• Living Room
    Living Room
  • Colony Calypso Private Deck Area and Main Entry door
    Colony Calypso Private Deck Area and Main Entry door
  • Front Entrance to Complex
    Front Entrance to Complex
  • Common Area Walkway
    Common Area Walkway
  • Common Area
    Common Area
  • Colony Calypso Private Deck
    Colony Calypso Private Deck
  • Full View looking towards Main Entry door
    Full View looking towards Main Entry door
  • Living Room
    Living Room
  • Living Room
    Living Room
  • Kitchen
    Kitchen
  • Full view from living room into kitchen looking at bathroom and bedroom door
    Full view from living room into kitchen looking at bathroom and bedroom door
  • Recently renovated Bathroom
    Recently renovated Bathroom
  • Bedroom with french doors that open onto front porch
    Bedroom with french doors that open onto front porch
  • Bedroom
    Bedroom
  • Bedroom
    Bedroom
  • Bedroom
    Bedroom
  • Bedroom
    Bedroom
  • Private back deck with seating
    Private back deck with seating
  • Private back deck with seating
    Private back deck with seating
  • Private back deck with seating
    Private back deck with seating
  • Shared Pool
    Shared Pool
  • Shared Pool
    Shared Pool
  • Shared Pool
    Shared Pool
  • Shared Pool
    Shared Pool
  • Key West
    Key West
  • Key West
    Key West
  • Key West
    Key West
  • Key West
    Key West
  • Key West
    Key West
  • Key West
    Key West
  • Key West
    Key West
  • Key West
    Key West

Colony Calypso

1 Bedrooms 1 Bathrooms Sleeps 4 Key West 526 sq. ft.

A charming one bedroom bungalow located in Historic Old Town Key West. This one level cottage has an open living/dining area, full kitchen and spacious bedroom with king size bed. Located on a compound with a large shared pool.

Bedroom

1 King

Living Sleeping Combo

1 Sofa Bed

Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is located just two blocks from world famous Duval Street. Colony Calypso is surrounded by coconut palms and blooming bougainvillea. This charming one bedroom bungalow is a true island hideaway.

The cottage features a one level open concept living and dining area with a full kitchen. The quaint cottage offers a spacious bedroom with a king size bed. The bathroom has a tiled shower bathtub combination.

The tropical common area grounds feature a large, beautiful swimming pool. Colony Calypso's convenient location and a quiet atmosphere make this a perfect place to relax in the comfort of your home away from home while still being in Old Town and close to Duval Street.

This vacation rental property offers secure, coded keyless entry with contactless check in.

Bedding: 1 king, 1 sleeper sofa

Parking: There is a small parking lot for cottage guests and available on a first come first parked basis. If the lot is full, there is on-street parking right on Olivia Street and on surrounding side streets and lanes.

Kitchen

  • Stove
  • Coffee Maker - Drip
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Cooking Basics
  • Oven
  • Dining table
  • Coffee Maker - Kcup

Location

  • Historic District

Tourist Attractions

  • Health Beauty Spa
  • Marinas, Boat Rentals & Excursions
  • Museums
  • Key West Aquarium
  • Public Parks & Beaches
  • Key West Historic Seaport
  • Key West Tropical Forest & Tropical Garden
  • Southernmost Point Buoy
  • Dry Tortugas National Park & Fort Jefferson
  • Fort Zachary Taylor State Park & Beach
  • Sunset Celebration at Mallory Square
  • History Tours - Motorized, Walking & Biking
  • The Florida Reef - N. America’s only living coral barrier reef
  • Key West Marine Park stretching from Higgs Beach to South Beach
  • The Key West Butterfly & Nature Conservatory
  • Food Tours
  • Ghost Tours
  • Pub Crawls
  • Your reservation guest portal will provide details

Accommodation Essentials

  • Hair Dryer
  • Hangers
  • Kitchen
  • Shampoo
  • Wireless Internet
  • Free wifi
  • Body Wash
  • Air Conditioning
  • Bed Linens
  • Cable
  • Towels
  • Hot Water
  • Essentials
  • Living Room
  • Iron & Ironing Board
  • Private Living Room

Sports

  • Paddle Boarding
  • Fishing - Surf
  • Hiking
  • Banana Boat Riding & Water Tubing
  • Wind Surfing
  • Ocean Waterpark & Challenge Course
  • Kayaking
  • Kite Boarding
  • Pickleball
  • Tennis
  • Golfing
  • Scuba Diving
  • Skydiving
  • Your reservation guest portal will provide details
  • Cycling
  • DeepSea Fishing
  • Fishing - Backcountry
  • Jet Skiing
  • Para-sailing
  • Fishing - Pier
  • Sailing
  • Snorkeling
  • Swimming

Leisure

  • Dolphin Watching
  • Dining Out
  • Live Theater, Concerts & Entertainment
  • Your reservation guest portal will provide details
  • Paint & Sip Art Classes
  • Bird Watching
  • Boating
  • Eco Tourism
  • Shopping

Local

  • Banks
  • Grocery Stores
  • Fitness Centers
  • Hospital
  • Laundromats

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Family

  • Bathtub

Car

  • Not Necessary

Entertainment

  • DVD Player
  • Satellite or Cable
  • Television

Outdoor

  • Garden or Backyard
  • Deck Patio Uncovered

Facility

  • Pool
  • Street Parking
  • Shared laundry on site

Pool

  • Communal Pool
  • Heated Pool

Themes

  • Historic
  • Romantic
  • Sports Activities
  • Tourist Attractions
LEAVE A REVIEW
July 23, 2026 - Track Survey

by Kimberly C

The place was great. Parking wasn't great due to construction and lack of non residential permit parking. Everything else was perfect!

Thank you for the 5 star review, despite the lack of parking.  Unfortunately, there are only a few parking spaces onsite and they are on a first come basis.  Finding free, non-residential parking can be challenging in this area, but there are nearby pay and park lots.  We are happy that you enjoyed the cottage and your time in Key West.

June 29, 2026 - Track Survey

by Felicia R

This was our 3rd time staying with RentKW at the Colony rental property. We were originally booked at a different location in KW to try a beach front place but the place did not work out. I called and was able to get into a Colony rental same day for the remainder of our stay. The location is perfect - close enough to Duval but far enough away to be quiet, clean and cozy unit, the grounds are very well kept (the guys work extremely hard every day!). We'll be back!

Thank you for your kind review and for staying with Rent Key West again! We're glad we could quickly find you a Colony rental and that you continue to enjoy the location, comfort, and well-kept grounds. We appreciate your loyalty and look forward to welcoming you back soon!

May 10, 2026 - Track Survey

by Michelle S

The cottage was great. Clean and perfect for two people. Our coffee maker stopped working and they brought us s new one right away. Only problem a hotel complex behind us loud music at their outdoor bar. Only a open wooden fence between them and our cottage. Yo could see the people roght behind yo. They would be there for brunch in the afternoon and evening. The only way we did not hear the loud noise voices and music was to stay insidevsnd kerp the doors to the lovely back deck closed. We could not sit out there or eat out there.there.

Thank you for your review and for sharing your experience. We're so glad to hear you enjoyed the cottage and found it clean, comfortable, and well-suited for your stay. We're also happy our team was able to quickly replace the coffee maker when the issue arose.

We sincerely apologize for the noise and lack of privacy caused by the neighboring hotel's outdoor bar. We understand how disappointing it must have been to have such a lovely deck space that you were unable to fully enjoy because of the music, conversations, and activity nearby. While this area is outside of our control, we recognize the impact it had on your stay and appreciate you bringing it to our attention.

Guest feedback like yours is invaluable, as it helps us better inform future guests about the surrounding environment and identify opportunities to improve the overall experience. Thank you again for staying with us, and we hope to have the opportunity to welcome you back in the future.

April 23, 2026 - Track Survey

by Marshall C

We love this cottage. Will return again

So happy to hear that you love this cottage! We absolutely look forward to your return stay~

February 18, 2026 - Track Survey

by Yvonne G

The cottage we rented was the perfect size for a week rental. The kitchen was appointed well enough to cook a few nice meals. Everything was clean and comfortable. We did need a few things that were missing from the description, and the staff was quick to make the adjustments for us. One thing for others to be aware of is the noise from the property behind our rental. The back deck of the unit is very near the bar and pool area of the property behind it. They have music and conversations at times during the day and it did impact our overall experience.

Thank you for your thoughtful review. We're delighted to hear that the cottage was the perfect size for your stay and that you found it clean, comfortable, and well-equipped for preparing meals. We're also glad our team was able to quickly provide the additional items you needed and help make your stay more enjoyable.

We appreciate you sharing your feedback regarding the neighboring property's bar and pool area. While many guests enjoy the vibrant atmosphere that comes with staying in the heart of Key West, we understand that noise from nearby businesses and outdoor gathering spaces can impact the experience for those seeking a quieter retreat. Thank you for mentioning this, as it can be helpful information for future guests when selecting the property that best fits their preferences.

We truly appreciate your feedback and are grateful you chose to stay with us. We hope to have the opportunity to welcome you back for another enjoyable visit in the future.

December 4, 2025 - Track Survey

by Cherryl K

As always, pleased with the properties and services provided.

October 21, 2025 - Track Survey

Great property

by Michael R

Great property. Professional, friendly staff (and GiGi the bulldog)

October 3, 2025 - Track Survey

Very cheerful

by Tara S

The Colony Calypso was a great place for a couple to stay. The whole cottage was full of light and very cheerful.

September 21, 2025 - Track Survey

Wonderful time.

by Kristina S

This little bungalow was perfect for us. We loved the pool and had a wonderful time.

July 5, 2025 - Track Survey

by Gia S

Clean and organized unit. Pool was great. Auto check in and check out (without having to drop off keys is a plus) i wish check out was at 11am instead of 10am. We would stay here again.

April 14, 2025 - Track Survey

by Lisa B

Everything was great!

March 26, 2025 - VRBO

First timers in Key West

by Bille-Jean B

Perfect location and size for two adults. The kitchen was well stocked with essentials for our visit. We walked everywhere. The location is very central to the old town. The pool was perfect for some sun and a swim. Easy check-in and check out.

January 16, 2025 - Track Survey

by Mary O

Everything was great

January 1, 2025 - Track Survey

by Jennifer A

We had an excellent stay. Looking forward to our next stay.

November 20, 2024 - Track Survey

by Mike P

Great property with everything that was needed. Good location.

November 16, 2024 - Track Survey

by Jessica J

Loved our stay!

May 15, 2024 - Track Survey

by John Slater

We had a wonderful time!

April 25, 2024 - Track Survey

by Cynthia M Williams

The new landscape, new shower & higher toilet. Nice quiet place to stay & would recommend to friends. Check in time needs to be earlier than 3 pm

January 24, 2024 - Track Survey

by Krista Clark

Unit was clean, charming, and exactly as described. The advance info was very helpful and the guest portal was easy to use.

January 10, 2024 - Track Survey

by Regina Eckert

Fabulous stay!

December 30, 2023 - Track Survey

by Pam Frederick

The location was amazing! Just a couple of short blocks to Duval St. Private patio was nice. I would say the furniture could be upgraded. The neighborhood was quiet and I felt safe walking.

December 18, 2023 - Track Survey

by Jason Osias

We’ve stayed in several of your properties and over all we’ve had great experiences. The only issues we had was that the bathroom door was very hard to close and paint would chip off. Also, the bathroom door did not lock.

Thank you for your 5 star review!  We have put in a maintenance request to fix the bathroom door.  Your feedback is greatly appreciated.

November 1, 2023 - Track Survey

by Michelle Resig

There wasn’t any baking dishes for the oven. The shower leaks water on the bathroom floor.

Thank you for the 5 star and your feedback.  We will be sure to have maintenance look at the shower leak and we will do an inventory of the kitchen supplies.  There should be baking dishes in the cottage.  We apologize for the oversight.  Thank you for staying with us and we hope to see you again.

May 4, 2023 - Track Survey

by Thomas Stickford

Rent Key West was great to work with. Friendly staff answered all questions. We were able to store luggage there between our arrival and check-in time. Great service!

Thank you for your Five Star review of Colony Calypso Key West. We are so glad that our friendly staff helped make your stay enjoyable.  We look forward to welcoming you back again soon!

April 4, 2023 - Track Survey

by Jacqueline Martucci

We loved our stay at Colony Calypso! The back deck seating area was the perfect place to both work and relax. The music at the hotel behind this property was loud at times, but wasn't unpleasant. The property felt properly equipped for our short 4.5 day stay. The pool area was lovely but it would be nice to see some additional chairs out there! On most days, all the pool chairs were already "claimed" by a larger group who was staying on property. The bed and couch were super comfortable. Overall, a great stay and we would absolutely return!

Thank you for your Five Star review of Colony Calypso Key West. We are so glad that the cottage provided the perfect place for your working and relaxing getaway.  We hope to elcome you back again soon!

January 15, 2023 - Track Survey

by steven Bernstein

The location was great. The place was great. It was everything you could ask for.

Thank you for your Five Star review of Colony Calypso Key West.  We are so glad that you enjoyed the cottage and its great location.  We hope to welcome you back soon!

December 17, 2022 - Track Survey

by Sandra Robey

Pleasant experience

Thank you for your Five Star review of Colony Calypso Key West.  We are so glad that you had a pleasant experience and we hope to welcome you back soon!

November 7, 2022 - Track Survey

by Gerry Williamson

This was the perfect rental for our long weekend stay. Close to all we wanted to do.

Thank you for your Five Star review of Colony Calypso Key West.  We are so glad that it was the perfect place for your vist and that you enjoyed its convenient Old Town location.  We hope to welcome you back soon!

October 26, 2022 - Track Survey

by Patrick Haskell

Ran into a few problems and they were promt on taking care of

Thank you for your review of Colony Calypso Key West.  We are so glad that the few issues that came up were promptly resolved.  We hope to welcome you back soon!

October 26, 2022 - Track Survey

by Stephanie H

We booked for our honeymoon - seeking a central/walkable location that was peaceful. Our unit was bright, clean and well stocked. The bed was very comfy. Loved our private patio for morning coffee. Only thing I was wanting, was a little more drawer space for clothing - but hey - it's Key West. All you need is a few outfits, swimsuits and flip flops! We regretfully had to leave early due to medical emergency. The wifi/cable would go out frequently - but usually popped back on in a matter of minutes. I appreciated the fast and professional responses from the staff as we booked and planned our arrival.

Thank you for your Five Star review of Colony Calypso Key West.  Congratulations again on your recent nuptuals and we hope the medical emergency was resolved quickly and with a very healthful outcome!  We are glad that you enjoyed the cottage and its peaceful property and convenient location.  We hope to welcome you back for your first anniversary or sooner!

July 1, 2022 - Website

Great get-away cottage!

by Karen P.

This cottage was a very nice quiet spot close to Duval. Restaurants, grocery,bakeries all within close walking distance, as well as Hemingway House and other attractions. With bicycles you could truly get anywhere. There was parking on-site. The unit air conditioners were very noisy but kept the place very cool,even in 100 degree heat. Pool was immaculately maintained. Unless you wanted to stay directly on Duval, this was a great place. Rental staff was very helpful when needed. We never watched TV, but I assume they worked. Who watches TV while in key West? Lusting pictures make the place look larger than it is, but i expected that. I would stay here again.

Thank you for your Five Star review of Colony Calypso. We are so glad you enjoyed the cottage, pool and the location. We look forward to welcoming you back soon!

June 1, 2022 - Website

Wonderful Vacation Rental

by Recent Guest
This rental was wonderful! It was a great size for two, very bright, and clean. We had everything we needed and the location was great. We added a couple of days to our stay since we were so happy with it. The bonus on this cottage was the private deck in the back. We will rent this cottage again.Manager's ResponseThank you for your Five Star review of Colony Calypso! We are so glad that you enjoyed the cottage and its location so much that you were able to stay a bit longer! We look forward to welcoming you back soon!
Thank you for your Five Star review of Colony Calypso! We are so glad that you enjoyed the cottage and its location so much that you were able to stay a bit longer! We look forward to welcoming you back soon!
April 1, 2022 - Website

Perfect Location!

by Recent Guest
This quaint little place is perfect for walking access to the main attractions in Key West. It was a little dated, but mostly clean. As other reviewers mentioned, the hotel behind this unit plays very loud musics during their brunch time. It was kinda annoying, but if you plan on being out all day, it’s inconsequential. The community pool was perfect, a little sunny, a little shady and never too crowded. I’d definitely Italy recommend this place!Manager's ResponseThanks for your review and recommendation. We greatly appreciate your feedback and hope to welcome you back soon!
Thanks for your review and recommendation. We greatly appreciate your feedback and hope to welcome you back soon!
January 1, 2022 - Website

Laid Back Key West

by Kent H.
Pleasurable
January 1, 2022 - Website

Laid Back Key West

by Recent Guest
Pleasurable
December 1, 2021 - Website

Tropical Serenity in Key West

by Recent Guest
This property is tucked away from the street, surrounded by lovely tropical plants and trees.The inner courtyard has a lovely swimming pool of azure blue tiles also surrounded by beautiful tropical plants. Zen like exterior that leads into the spacious, colorful and comfortable interior space.Large spacious living room with vaulted ceiling, a kitchen with all the practical amenities, and a spacious bedroom with an amazingly comfortable king size bed. Having stayed in many VRBOs over the past 15 years, this one exceeded expectations immediately. Aesthetically, the soothing colors used for walls & furnishings as well as the artful touches of photographs of iconic places around Key West were a perfect complement to the sense of having everything you need on a practical level. The outdoor patio provided a haven for coffee in the morning and a cool drink in the evening before venturing out to dinner. The apartment is very conveniently located yet away from the frenzy of Duval St. We were able to walk or ride our bikes everywhere we needed/wanted to go. Highly recommend this oasis in Key West. We will definitely return! Thank you to the owners and management for a superb experience.
October 1, 2021 - Website

Wonderful little condo on a quiet street!

by David L.
Perfect getaway for the solo traveller or a couple wanting privacy. Located on a quiet side street in the middle of the key, this unit is just a 5 minute bike ride from everything.
October 1, 2021 - Website

Wonderful place!

by Sharen B.
The cottage was just perfect. Wonderful deck, peaceful, pool access and friendly neighbors. There's a little grocery up the street and just a short walk to the Duval loop stop or a few more blocks and you're on Duval or at the Southernmost point. Clean, bright, cheery.
October 1, 2021 - Website

Vacation

by Sharon R.
Great
September 1, 2021 - Website

Loved it!

by Staci D.
Husband and I stayed for a week. Loved the cottage! Very comfortable and cozy. Had everything you needed, including beach towels! Requested extra pillows and they were delivered a couple of hours later. And I cannot say enough great things about the folks at Rent KW. They were so friendly and accommodating. We were able to drop our luggage at the office for a few hours before our flight.The pool was refreshing and we met so many fun couples that were staying in some of the other cottages. Great location to walk to most things too!
August 1, 2021 - Website

Colony Calypso 8/7-8/13

by Karl A.
A last minute change in accommodations brought us to this cottage. The unit is quaint...probably only suitable for couples as it’s 1BR. Others would have to sleep on the pull-out. The unit was very clean and everything appeared in working order. We used the nice semi-private patio for breakfasts and relaxing. Pretty much everything you’d want is within walking distance. We met the owners who were very pleasant and always eager to provide us with restaurant recommendations, etc.... What started out as a stressful vacation (due to having change accommodations) ended up being very enjoyable.
July 1, 2021 - Website

Holiday Getaway

by Mike T.
We had an enjoyable time in KW. Our Accomodations were clean, comfortable and convenient.
May 1, 2021 - Website

Colony Calypso cottage #4

by Sandra H.
This rental was perfect. Close to everything you would want to visit on Key West.The cottage was clean, kitchen had everything you would need to cook with. The bed was comfortable and also had a TV as did the living room. The pool was an added bonus coming back from a hot day out and about. It was nice to take a dip in the late afternoons. Would definitely recommend this rental .
March 1, 2021 - Website

1st trip after Covid19

by Recent Guest
The pool is very nice, great location. The back deck is nice but chairs & grill could use updating. There is evidence of water damage under the kitchen sink including mold. But overall very nice. Kitchen well stocked for cooking/eating.
March 1, 2021 - Website

Calming, Charming, Cheerful Colony Calypso!

by Lisa J.
This was my second stay at The Colony. As we had no car, Jann was kind enough to have our luggage delivered to the cottage after we checked in. This enabled us to walk the few blocks to our unit unencumbered. We had no issues with the rental while we were there, but we knew that Jann was just a phone call away, if need be. Colony Calypso was exactly as described: very clean, comfortable and nicely appointed. The pool was lovely and well maintained - nice to come home to after a day on Higgs Beach. Our cottage had everything we needed for our stay. It was wonderful to have both a front patio as well as a rear patio for privacy. This is a great cozy space! Hemingway House is just a few blocks away and a must-see. It was fun to stroll the neighborhood, see the colorful architecture and end your day at Mallory Square for dinner and a spectacular sunset view. You can’t go wrong with any of the restaurants, but try Two Friends Porch or Harpoon Harry’s for breakfast, the Green Parrot for drinks, and Salute! (located right on Higgs Beach), Conch Republic Seafood Company and The Waterfront Brewery for dinner, just to name a few. I highly recommend Rent Key West Vacations and specifically The Colony, if you are headed to Key West. I certainly hope to return a 3rd time to this cozy oasis. It’s my happy place!
February 1, 2021 - Website

Wonderful cottage in the middle of Key West

by william y.
We loved our stay! We rented a car but ended up walking or riding bikes most of the time.Pool was clean and warm. Loved our private deck
February 1, 2021 - Website

Except for one issue this would be a 4-5 star rental

by Tyler T.
In a fantastic location to walk or bike to most everything, this unit was clean and as described. Very well managed and responsive. One small issue is the couch was very uncomfortable. One large issue is there is a hotel pool and an outside bar directly behind the unit just on the other side of the fence. We never could use the back patio which is something we really enjoy. From day one throughout the entire stay the music, bar patrons and those at the pool were very loud. At times the music at the bar shook the windows. While KW has a noise ordinance after 10 p.m. apparently there isn’t any rule until then. If this issue didn’t exist I’d give this 5 stars and probably stay again. On the day before we left I was talking with another couple staying one unit away from us and they informed me that they thought we were having parties every night. It’s that loud. If you can tolerate the noise then its a good place to stay, but I will not nor would I recommend it to a friend.
January 1, 2021 - Website

Perfect Getaway in Key West

by Cory R.
My wife and I had an absolutely terrific time and enjoyed riding our bikes all over the island. We REALLY thought the condo was our perfect scenario. Thank you so much for the great welcome and helping us enjoy the heck out of our vacation. Great 5year anniversary!
January 1, 2021 - Website

Private tropical retreat, just a short walk from everywhere

by Ryan T.
We loved this place. We could walk and bike everywhere we wanted. The shared heated pool was wonderful in January. Banana trees, elephant ears, and mango trees give the entire place privacy. There is a nice private little back porch with lounges to unwind on. The inside of the condo is very nice and just enough space for a couple. The bed and linens are great. The owner and management company were all very courteous and easy to deal with. The only issues we saw were very minor ones. The smoke detectors were taken apart or missing, the kitchen a/c unit showed visible mold inside, and the couch was pretty beat up. I’m sure the place will get these issues resolved soon. We would come back here every year if we could.
December 1, 2020 - Website

Perfect place to stay in Key West.

by Sandra R.
Quiet and a great location. Office staff and maintain staff friendly and efficient. The fourth year I stayed there.
December 1, 2020 - Website

Perfect place to stay in Key West.

by Recent Guest
Quiet and a great location. Office staff and maintain staff friendly and efficient. The fourth year I stayed there.
November 1, 2020 - Website

Key West

by Joseph G.
Great!!
November 1, 2020 - Website

Key West

by Joseph Vincent G.
Great!!
July 1, 2020 - Website

Key West Trip

by Alan C. A.
Up until I had an emergency and had to ck. out early , it was great. Joyce could not have been anymore helpful. When I had to leave 3 days early I didn't know what to expect! Joyce gave me a credit for the 3 days I missed w/o me even talking to her. This is the company I will use in the future and have already gave there info to some friends of mine. Other lady in the office is a little rump sprung- so I'd talk to Joyce!!!!
March 1, 2020 - Website

40 yr anniversary

by Mary F.
What a lovely charming place. Close to everything and a great pool. MGMT company helped me secure a package shipped here and we're very helpful.
January 1, 2020 - Website

Key West Unit

by Recent Guest
Was very disappointing after traveling for 14 hours to not have hot water when we arrived to shower and had to shower in cold water that night and the following morning. This is inexcusable for the cost per night. In addition, I did not appreciate the property manager talking to me the next morning like I didn't know how to operate a shower - at 61 years old, I've operated plenty of showers. The place is in a great location, clean, but very small - I would not recommend it for more than one couple or a couple with 1-2 small kids. There is limited parking out front so if you get one of those spots, if you don't have to move your car, don't - street parking in the area is impossible to find. Recommend the Little Pearl for seafood just one block away.
January 1, 2020 - Website

Very much enjoyed the stay

by Recent Guest
Nice place, good location.
November 1, 2019 - Website

Great Location

by Deana S.
Can’t wait to stay again!
October 1, 2019 - Website

Great place to stay!!

by Karen M.
The pictures are exactly how the rental is! We loved staying here! Convenient and quite! Felt like we had a private pool too! It was a great place to stay!
July 1, 2019 - Website

Great little house

by Norman G.
Great location, small but great for just 2 people
May 1, 2019 - Website

Key West Discovery

by Recent Guest
Loved this quaint little cottage enclave. Nicely landscaped grounds. Nice pool area. Pool could use some tile repair. Our unit was very clean and. I let furnished. Patio furniture and grill could be updated.
May 1, 2019 - Website

Key West Discovery

by Renee M.
Loved this quaint little cottage enclave. Nicely landscaped grounds. Nice pool area. Pool could use some tile repair. Our unit was very clean and. I let furnished. Patio furniture and grill could be updated.
April 1, 2019 - Website

Family Vacation 3019

by DIANE A.
I’ve rented this spot in the past and still as wonderful! Having a kitchen to make breakfast, a barbecue in the back for dinner, is a big money saver. The grounds are cleaned every day and immaculate. The pool was refreshing. Can’t wait for my next stay
April 1, 2019 - Website

Jannie&BeckVacay

by Rebecca Q.
Great location, private accommodations, well kept resort.
April 1, 2019 - Website

Family Vacation 3019

by Diane A.
I’ve rented this spot in the past and still as wonderful! Having a kitchen to make breakfast, a barbecue in the back for dinner, is a big money saver. The grounds are cleaned every day and immaculate. The pool was refreshing. Can’t wait for my next stay
January 1, 2019 - Website

Key West getaway

by Recent Guest
We were pleased with the rental. The accommodations were as described and centrally located as promised. The unit was clean and comfortable. It could have used a few more ammenities such as kitchen towels and dish clothes. It also didn't have anything in writing to answer common questions. Such as where to find the sheets for the couch pull out. They were in a container under the bed but we didn't think to look there and thus had to spend the first night sleeping in the same bed, which was not desired. The rental staff were friendly and helpful in storing our luggage on day of checkout.
January 1, 2019 - Website

Winter Get Away

by Recent Guest
Very nice place, good location, clean and private
November 1, 2018 - Website

Charming Cottage

by Recent Guest
Great location in a quiet neighborhood but within walking distance of everything we needed
November 1, 2018 - Website

Perfect Description!

by Rodney Y.
Far too often, when you rent a place based on photos, you are sorely disappointed. Not the case here. The photos are spot on. It is perfect for two and the location is excellent. Can't wait to return and definitely recommend this little gem. Everything was just perfect!
October 1, 2018 - Website

Calypso

by Ronald L.
House was nice. Clean and in good shape. Pool was good. Wish there had awnings over outdoor seating areas. Parking needs to be improved. Only four spaces for six rental units.
September 1, 2018 - Website

Best vacation spot ever

by James A G.
Relaxing quiet yet a short walk to all the highlights Key West has to offer. We definitely are going back soon!
July 1, 2018 - Website

Key West Honeymoon

by Recent Guest
Kudos to the Rent KW team. Professional, accessible, and all-around impressive. We arrived after hours, but we had been given step by step instructions on how to get our paperwork, access code, etc. The property was easy to find, very clean, and exactly as the pictures depicted. The location was good if you take it for what it is. (It's Key West, so expect to walk a little bit!) Two blocks off of Duval St, so you can easily walk to all of the tourist stops, bars, restaurants, etc, but tucked back in a nice, quiet neighborhood.It was warm the week we were in town, so the pool (and a well-maintained one at that!) was a lifesaver. It's tucked back in the compound, so you actually have pretty good privacy for a community pool! All the guests that were staying on the grounds seemed to enjoy it. We had a great overall experience. Good work Rent KW.
July 1, 2018 - Website

Key West Stay

by Recent Guest
Came to relax. Area was nice. Unit had drywood termite bodies on sills, kitchen had mold under sink and the wall units have mold growing inside the units.
March 1, 2018 - Website

Oloony Calypso

by Maryanne A.
We really enjoyed our stay. Great location close to everything. Cute, immaculate sun filled cottage. Would come back to stay here again.
March 1, 2018 - Website

Colony Calypso

by Recent Guest
We enjoyed our stay. The team at Rent KW are wonderful. The location can't be beat, very quiet and in the heart of the best part town walkable to everywhere. The accommodations are basic but the price is a total bargain for the space and privacy. The landscaping is well kept and attended to regularly. As far as the other exterior areas, the pool, laundry facilities, and building exteriors could use a little maintenance.
January 1, 2018 - Website

Quiet, clean, quaint

by william s.
Unit 4 is perfect for a couple. Walk everywhere The staff is very helpful.
August 1, 2017 - Website

Two Thumbs Up for Colony Calypso!

by Allison M.
We had the most amazing stay at the Colony Calypso! We have been vacationing in Key West for the past 20 years and my husband and I agreed this was one of our best stays (second only to our wedding!). The room was clean and updated and fit our family perfectly. The private back balcony was so nice for meals and the kitchen was certainly large enough to be able to prepare meals for us and the kids. The bedroom is quite large and had plenty of room for the crib. The 2 boys fully enjoyed sleeping on the pullout in the living room as well. The best part was the big pool! We really couldn't have asked for a better stay!
July 1, 2017 - Website

Much needed vacation

by Sonia E.
There is nothing negative to be said, we had the most relaxing vacation and was definitely well needed. We loved the property and the convenience to everything that we wanted to visit. We also met a lot of super people and the staff at the rental agency couldn't have been any more helpful. Will visit again and rent in the same area again.
July 1, 2017 - Website

Quaint Cottage - perfect for 2!

by Theresa O.
Rented this quaint cottage just blocks off Duval Street. It's perfectly situated to all restaurants and beaches. It was easy to find and to bike to the marina to the beach to Duval street. Parking is first come first serve which was an issue but other than that, the cottage was beautifully decorated and furnished. We loved having a private back patio to come home to and a shared pool was great! We will definitely book again! Great linens and kitchen was well equipped as well. We didn't use it much with all the great restaurants around but it's nice to have it when you need it.Manager's ResponseThank you for the great review! We are happy to hear that you enjoyed the cottage. You are right about parking being first come, first serve, but there are also many free street parking spots near the cottage. Next time, we would be happy to give you other parking options if the cottage parking lot is full. We look forward to you staying with us again!
Thank you for the great review! We are happy to hear that you enjoyed the cottage. You are right about parking being first come, first serve, but there are also many free street parking spots near the cottage. Next time, we would be happy to give you other parking options if the cottage parking lot is full. We look forward to you staying with us again!
June 1, 2017 - Website

Just what we needed

by Will H.
Clean, comfortable, great location, nice pool, and very quiet. We had no complaints whatsoever and were extremely happy with the accommodations. Unless we win the lottery and can afford to buy a vacation home in Key West, we'll be staying here.
April 1, 2017 - Website

Great stay!

by kris m.
We had a great time and great stay! Very clean and great location. I would stay here again for sure. (We had ants and kept all food in the refrigerator, but not a deal breaker. Bought some traps and all was good.)
April 1, 2017 - Website

Great stay!

by Kris M.
We had a great time and great stay! Very clean and great location. I would stay here again for sure. (We had ants and kept all food in the refrigerator, but not a deal breaker. Bought some traps and all was good.)
March 1, 2017 - Website

Excellent Stay at a Fun Destination

by Lee S.
Colony Calipso was a wonderful place to stay in Key West!The cottage was inviting, clean and equipped very well.One of maybe eight cottages around a pool. Private, yet, we met most of the neighbors. As nice, or better than pictures. The kitchen was the best equipped of any vrbo we've stayed at. My wife was able to cook gourmet meals.Calypso is walking distance to most everything. We would recommend rent a scooter. Parking for a car is difficult, and streets are narrow. With the scooter we could reach many places, zip back to Calypso and then head out again- enough we were forgetting what day it was.Between Calypso, the scooter and Key West we felt like teenagers.
January 1, 2017 - Website

Beachy

by Recent Guest
The property was immaculate and quiet! The unit was fully stocked with bath and beach towels, coffee filters, dish washing detergent, paper towels and two air conditioners and two televisions!Only one negative; no beach chairs for us to take to the beach. The local rental company had only one small sit upon chair. We love the beach at Zachary Taylor State Park. El Sorbey Restaurant for Cuban food and Pepe's Restaurant for atmosphere.
January 1, 2017 - Website

Perfect choice

by Jason I.
Best location and advertised right. The cottage was clean and in great condition. The rental company was excellent and had us in there immediately even with and early arrival. It was quiet and very comfortable. Thought it leave. Highly recommended for 2, not sure of 4. Went during winter months so sun was low and pool in shade a bit so maybe some selective brush clearing would be good but that is about it.
December 1, 2016 - Website

Perfect Place for Key West Getaway

by Tim R.
This property was awesome. It was perfect for what I needed. Close to Duval and was able to walk anywhere in Old Town. Overall, a great property.
December 1, 2016 - Website

Colony Calypso

by Wendy S.
We had a wonderful stay at Colony Calypso. Extremely private and just far enough away from Duval Street to be quiet but close enough to walk everywhere. There were just a couple instances where we used our car and that was simply because we were doing water activities and didn't want to have to walk home in beach attire. The accommodations were clean and provided everything we needed for a weeks stay. Would rent this property again.
November 1, 2016 - Website

Nice Vacation

by Recent Guest
Hi,The only complaint I would have is the tub water did not drain and you are taking a shower in standing water. I think that is gross. All in all the place was great and I for sure would be backKaren Manager's ResponseThank you for taking time to review our property, Colony Calypso. Your feedback is important to us. We are happy to hear that you enjoyed your stay. As for the shower not draining, we would have sent our maintenance staff over right away if you had reported the problem to us while you were here. The shower drain is now fixed. We greatly appreciate your feedback and hope you will stay with us again.
Thank you for taking time to review our property, Colony Calypso. Your feedback is important to us. We are happy to hear that you enjoyed your stay. As for the shower not draining, we would have sent our maintenance staff over right away if you had reported the problem to us while you were here. The shower drain is now fixed. We greatly appreciate your feedback and hope you will stay with us again.
July 1, 2016 - Website

Colony Caylpso

by Steven T.
The cottage was exactly as it is shown in the pictures and the management office was very helpful. We arrived before the unit was ready and the office let us keep our bags at the office and offered to deliver them directly to our cottage. They even gave us several suggestions for local restaurants to have lunch at while we waited. The pool area was beautiful and we felt like we had our own oasis just a couple of blocks off of Duval Street!
April 1, 2016 - Website

Key West Getaway

by Virginia L.
My husband and I were looking for a place to relax and unwind from the cold of New York. This was the perfect set up and location for us. Close to lots of great restaurants and local attractions. The place was clean and the pool was wonderful. The property manager was very helpful in giving us directions to attractions and places to eat. I recommend this to anyone who is looking for a pleasant stay in beautiful Key West.
March 1, 2016 - Website

Very clean, awesome location!

by Recent Guest
If you are a couple looking for a perfect location on Key West, give this little gem a try. I wouldn't try to squeeze more than two in here, it is cozy. But it was just perfect for the two of us. Location is perfect, halfway between Atlantic and Gulf side activities. Walk to the ocean for lunch and meander back to the gulf side for evening sunset, etc. The management company was great to work with. Pool area was very well maintained. Parking is tricky but you don't need a car here. There is a little grocer one block away. If you have a car, park it and leave it. The unit was VERY clean. A brand new memory foam mattress was delivered the day before we left. Deck is not huge but who wants to hang out on the back deck when you can be checking out all the sites in KW.
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September 2026
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$157
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$196
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$151
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$174
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$208
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$183
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$154
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October 2026
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$212
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$222
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$257
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$268
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$273
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$240
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$277
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$259
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$300
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$334
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$394
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$384
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$419
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$367
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$396
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$337
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$318
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$319
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$355
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$316
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$324
November 2026
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$309
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$309
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$511
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$416
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$325
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$348
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$351
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$390
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$384
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$369
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$345
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$316
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$309
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$314
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$356
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$346
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$358
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$334
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$311
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$259
          
December 2026
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$291
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$286
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$294
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$330
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$340
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$334
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$294
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$275
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$269
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$289
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$322
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$352
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$370
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$363
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$382
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$404
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$424
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$456
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$528
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$620
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$600
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$608
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January 2027
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$580
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$506
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$494
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$497
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$511
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$515
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$510
10
$449
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$430
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$427
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$443
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$484
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$569
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$600
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$555
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$484
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$488
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$467
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$525
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$536
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$538
24
$482
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$475
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$527
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$529
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$554
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$584
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$613
31
$489
            
February 2027
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$466
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March 2027
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$607
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$607
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$603
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$636
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$639
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$633
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$554
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$516
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$507
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$523
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$568
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$591
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$595
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$529
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$519
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$475
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$490
      
April 2027
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$520
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$548
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$543
04
$470
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$449
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$435
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$446
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$483
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$503
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$500
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$442
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$419
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$414
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$426
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$464
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$484
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$487
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$425
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$403
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$399
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$407
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$449
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$467
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$473
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$425
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$401
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$395
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$449
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$481
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$505
  
May 2027
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$513
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$390
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$367
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$360
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$365
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$397
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$427
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$415
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$361
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$464
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$354
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$345
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$345
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$361
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$400
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$413
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$395
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$356
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$381
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$378
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$377
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$375
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$386
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$386
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$365
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$361
          
June 2027
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$357
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$345
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$345
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$364
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$366
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$345
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$345
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$345
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$345
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$348
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$369
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$376
13
$345
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$345
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$345
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$345
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$360
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$378
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$382
20
$345
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$345
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$345
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$345
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$350
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$369
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$368
27
$345
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$345
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$345
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$345
      
July 2027
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$383
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$387
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$406
04
$388
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$346
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$345
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$349
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$376
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$402
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$371
11
$345
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$345
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$345
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$345
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$348
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$368
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$373
18
$345
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$345
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$345
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$345
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$358
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$395
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$439
25
$387
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$393
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$408
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$395
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$417
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$421
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$370
August 2027
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01
$345
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$345
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$345
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$345
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$345
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$347
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$353
08
$345
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$345
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$345
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$357
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
        
September 2027
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
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$345
    

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