Ann Street Cottage

1 Bedrooms 1.5 Bathrooms Sleeps 2 Key West 671 sq. ft.

Ann Street Cottage is a one bedroom one-and-a-half bathroom cottage on a tropical compound with a shared pool. Located steps off Duval next to The Curry Mansion.

Bedroom

1 King

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. Summer of 2020 update: Bathrooms have been remodeled and a private laundry is now in the unit.

The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to see why this location is unbeatable. The shared compound, of 6 total homes, features a winding brick pathway surrounded by tropical foliage and flowers that lead to a free form heated pool tucked away in the far side of the gardens. Take a refreshing dip, lounge and catch some sun, or enjoy a good book while being surrounded by beautiful trees and plants. This truly is a relaxing outdoor oasis!

Upon entering Ann Street Cottage you'll feel refreshed by the cool and relaxing decor. Neutral colors combine with pops of tropical color throughout to create an inviting atmosphere to relax in. Lounge in the living room while reading a great book or catch the morning news. Transom windows let in light and the vaulted ceiling creates a bright and airy atmosphere. A small dining table for two sits just off the fully equipped clean white kitchen. A half bathroom is conveniently located next to the kitchen. The bedroom combines island charm with boutique hotel style complete with full en-suite bathroom. Calming hues and pops of coral and teal will lull you to sleep after a busy day of exploring the island. French doors open out to the private patio with outdoor dining table from the bedroom and living room. A small office space with desk and chair are located behind the patio, in case you must get some work done. The washer & dryer is in this office space as well.

Ann Street Cottage combines a peaceful hideaway with excellent location making it the perfect option for a couple looking to have the ultimate Key West experience.

(The Ann Street Compound Homeowners Association requires all occupants to be 16 + yrs. Regretfully, NO Children under 16 allowed. This home is also not pet-friendly) STREET PARKING ONLY

Bedding: 1 king bed

Attractions

  • Marina
  • Museums

Essentials

  • Air Conditioning
  • Bed Linens
  • Towels
  • Wifi
  • Hot Water
  • Dryer
  • Essentials
  • Hair Dryer
  • Iron & Ironing Board
  • Kitchen
  • Washer
  • Wireless Internet
  • Free wifi
  • Wifi speed 25mbps

Accomodations

  • Breakfast: Not Available
  • Cleaning: Optional

Kitchen

  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Stove
  • Cooking Basics
  • Dishwasher
  • Oven
  • Dining table

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Leisure

  • Bird Watching
  • Boating
  • Eco Tourism
  • Shopping

Local

  • Fitness Center
  • Hospital
  • Laundromat

Sports

  • Cycling
  • DeepSea Fishing
  • Fishing
  • Fishing - Bay
  • Jet Skiing
  • Para-sailing
  • Pier Fishing
  • Racquetball
  • Sailing
  • Snorkeling
  • Swimming

Car

  • Not Necessary

Entertainment

  • DVD Player
  • Stereo
  • Television

Facility

  • Pool
  • Street Parking

Location

  • Historic District

Outdoor

  • Deck Patio Uncovered
  • Fenced Yard

Pool

  • Communal Pool
  • Heated Pool
LEAVE A REVIEW
June 1, 2022 - Website

Exactly as Described

by Recent Guest
Property was conveniently close to everything, yet was quietly tucked away. Pool area was perfect for relaxing with beautiful landscaping. Cottage was clean and well equipped with everything we needed. Once we figured out the hot water in the shower, we were all set! Property management was very helpful when needed. Would highly recommend and would stay again in a heartbeat!Manager's ResponseThank you for your review of Ann Street Cottage and your recommendation. We are so glad that you enjoyed your stay and we look forward to welcoming you back soon!
Thank you for your review of Ann Street Cottage and your recommendation. We are so glad that you enjoyed your stay and we look forward to welcoming you back soon!
June 1, 2022 - Website

Key Lime Cottage

by Scott M.
We can't say enough about how great a time we had in this key lime pie inspired cottage. The cottage had everything we needed right down to a few beach chairs, beach towels, and an umbrella.Location, location, location... just one block from the heart of old town Key West and a half block from SunShine Scooter rentals (a must do activity). Despite the close proximity to Duval St we were surprised how quiet it was at night and throughout the day.The pool is beautiful and private with a luxurious giant royal palm guarding and providing shade.We will definitely be back!Manager's ResponseThank you for your Five Star review of Ann Street Cottage and your recommendation. We are so glad that you enjoyed the cottage and its quiet, convenient location. We look forward to welcoming you back soon!
Thank you for your Five Star review of Ann Street Cottage and your recommendation. We are so glad that you enjoyed the cottage and its quiet, convenient location. We look forward to welcoming you back soon!
June 1, 2022 - Website

Fantastic little cottage!

by Anthony A.
We were quite surprised at what a tropical oasis Ann St is. We were not expecting the lush tropical foliage as we walked up the path to the door, it got even better as we walked to the pool. Absolute relaxation, pool was the perfect temperature and had plenty of seating if you didn't want to relax in the pool.The cottage itself was excellent, very clean and very comfortable with an AC unit in the living room area and one in the bedroom. And being a block and half off of Duval was extremely convenient to get to but also it was nice and quiet at the cottage.We would absolutely pick this complex again with no hesitation.Manager's ResponseThank you for your Five Star Review of Ann Street Cottage! We are so glad that you enjoyed your stay and we look forward to welcoming you back soon!
Thank you for your Five Star Review of Ann Street Cottage! We are so glad that you enjoyed your stay and we look forward to welcoming you back soon!
May 1, 2022 - Website

Lovely cottage in great location

by Michael B.
Ann Street Cottage is located less than a block from Duval in its own private garden oasis. The cottage was quiet, roomy, and comfortable. The grounds are absolutely beautiful and well-maintained. The shared private pool was a welcome bonus. Duval Street, Mallory Square, the historic marina, restaurants, bars, sites, etc. are all an easy walk away. Unless you're lucky enough to get a free parking spot on Ann St., parking is not cheap at nearby lots but it's not difficult either. We'd recommend ditching the car and navigating Key West on foot or by bike! We were very happy with our stay at Ann St. Cottage and would definitely rent here again.Manager's ResponseThanks so much for your review. We are very happy that you enjoyed your time at Ann Street Cottage and we look forward to your return!
Thanks so much for your review. We are very happy that you enjoyed your time at Ann Street Cottage and we look forward to your return!
April 1, 2022 - Website

Excellent Location

by Judy J.
Excellent location and very quiet. Property management offered to keep our luggage for us since we had a late flight so we could enjoy our last day on this beautiful island. Definitely will be back.Manager's ResponseThank you for your review of Ann Street Cottage. We are so glad you enjoyed the cottage and its excellent, quiet location. We greatly appreciate your recommendation and look forward to welcoming you back soon!
Thank you for your review of Ann Street Cottage. We are so glad you enjoyed the cottage and its excellent, quiet location. We greatly appreciate your recommendation and look forward to welcoming you back soon!
March 1, 2022 - Website

Beautiful Place

by Edward F.
Ann Street Cottage was a great little property for my wife and I. Small complex with a beautiful, quiet, peaceful pool area and close to pretty much everything Key West.
February 1, 2022 - Website

Ann Street Cottage

by Anthony and Geraldine P.
We just love all the cottages! This was our first stay in Ann Street Cottage, because we usually stay in Ann Street Tranquility. We love the location! Having two bathrooms was a real plus for us!
December 1, 2021 - Website

Amazing tranquil oasis

by Sonesh C.
This property was amazing -- great location, peaceful, immaculate, charming, filled with foliage, and somehow quiet though a hop, skip and a jump from Duval. Will definitely come back!
December 1, 2021 - Website

Great location

by Amy B.
Location is key for this quaint little cottage. We stayed here without a vehicle and was within walking distance to everything we wanted to do. The cottage was comfortable but showing its age. For example....some cracked floor tiles, porch doors that were warped and almost impossible to open and close. The bed was comfy and the kitchen had everything in it we needed to cook a few small meals. The cottage was very quiet at night despite its close proximity to night life. We would recommend staying here if you want to be close to Duval, it’s nightlife, and the harbor/Mallory square.
November 1, 2021 - Website

Quiet little place in the middle of eveything!

by JILL Y.
Surprisingly quiet little cottage considering the location. Really enjoyed and would definitely come back to this location given the right price.
October 1, 2021 - Website

Twice the Charm

by Recent Guest
This was our 2nd visit to the Ann St Cottage. It's a perfect little place for a couple in a great location. We will definitely stay here again and the air conditioning will freeze you out:)
September 1, 2021 - Website

Loved it!

by Recent Guest
Lovely property. Very relaxing area but still close to the action. Wish my vacation was longer, but it really was delightful. Would definitely reboot at this property.
July 1, 2021 - Website

Location Location Location

by LANCE J.
Very nice cottage. Great Location! Just right for a couple.
June 1, 2021 - Website

Quiet, great location

by Melissa A.
The unit was clean and super well stocked. Loved having two bathrooms and the washer and dryer were a huge plus! We would have brought a duffle bag instead of checking luggage had we realized what an asset that would be. So nice after a hot sweaty day to wash your clothes. Staff was nice. Only complaint was the shower didn't get hot. We noticed that it had been redone recently and it could just be that the valve needs adjusted. Would definitely stay here again. You couldn't ask for a more convenient location to everything
June 1, 2021 - Website

Amazing rental

by Recent Guest
The place we rented was amazing and very close to things to do. I definitely recommend it if you get the chance to rent this property. The pool area was beautiful and so was the rest of the property.
May 1, 2021 - Website

Back in paradise.

by judith g.
Perfect private quiet little house. Has everything you need- very well supplied.
April 1, 2021 - Website

Much Needed Getaway in Secluded KW Paradise

by Palmer H.
We could not be happier with our week at Ann Street Cottage, and we will only stay here for our future KW visits. We stayed at Bali Hideaway (located in the same compound) 11 years ago, and we also enjoyed it very much. However, we do prefer this cottage due to the larger king size bed, extra half bath, private courtyard patio, and private laundry. The location is within easy walking distance to all of our favorite spots in Old Town. It is amazing that you can enjoy such peace and quiet literally just steps away from the Duval Street party scene. We had no need to contact management the entire week, so that speaks volumes for the preparation of the cottage. Honestly, it was tough leaving this place to head back home! This might be KW's best kept secret, so don't tell anyone. 😉
April 1, 2021 - Website

Made for the perfect getaway

by Recent Guest
Couldn't have been happier with the experience. Great unit and spectacular location. Wish we had stayed an extra night or two.
March 1, 2021 - Website

Fun in Key West

by Recent Guest
Beautiful home plenty of space comfortable king sized bed Pool is gorgeous
February 1, 2021 - Website

Awesome stay!

by Alison H.
Would definitely rent this place again. Perfect location! One block from Duval Street so it was easy to walk everywhere and enjoy the night life, but was also far enough away that it was private and quiet. This is a perfect little cottage for two with a full kitchen and extra half bath. The private courtyard patio was our breakfast spot and we spent much time by the pool which sometimes we had by ourselves and sometimes not. My only suggestion to property management is there is no blanket. My husband was hot and I was cold, there was no blanket. Other than that simply perfect. Would highly recommend! We will be back.
January 1, 2021 - Website

Quiet, private, and perfect location

by Blaine C.
This is the perfect cottage for two, in the perfect location. We did not use the kitchen, but everything else was fantastic and exactly what we needed!! Bike rental company just around the corner makes Fort Zachary Taylor only a 10 minute ride away. Older Key West is just a 10-15 minute walk. Couldn't believe how close we were to Duval without all the commotion and noise. Can easily Uber to further destinations if needed. We were thankful we didn't have a car to mess with parking. Check-in and out was a breeze. It was nice to have a keypad lock and not worry about keys. We already plan to stay here again! Thank you!(sidenote to rental company: the master bedroom door sticks pretty bad in the upper corner--we were worried it would break with trying to get out in the mornings! Could easily be shaved down or something)
January 1, 2021 - Website

Best location!

by Recent Guest
We have stayed at several of the places on Ann Street, and will keep coming back!
November 1, 2020 - Website

Relaxing cottage

by Recent Guest
Overall, it was a pleasant stay. Cottage was clean, more than enough for our needs. I would only say an e tea blanket would be nice. We like it cool at night, but the thin cover & sheet was not enough. Everything else was very nice. Except the weather! Oh well!
June 1, 2020 - Website

Escape to Key West

by Thomas H.
We were very happy with the cottage. It was very clean and well prepped for our visit. The location is perfect for walking around town. We plan to stay there on our next visit.
March 1, 2020 - Website

Home away from home

by Recent Guest
Outstanding!!!
March 1, 2020 - Website

Home away from home

by Ken S.
Outstanding!!!
February 1, 2020 - Website

Ann Street 2 a home away

by James and Patricia C.
Our second year in this cottage and we know we will be back. Lovely and spacious, this cottage feels like home and has everything needed for your stay. Close to Duval but closed in and peppered with the tropics you enjoy the pool and the quiet. Joyce our agent is welcoming and most helpful. We have also stayed at Bali on Ann Street and although smaller, still is great!!
February 1, 2020 - Website

Ann Street 2 a home away

by James C.
Our second year in this cottage and we know we will be back. Lovely and spacious, this cottage feels like home and has everything needed for your stay. Close to Duval but closed in and peppered with the tropics you enjoy the pool and the quiet. Joyce our agent is welcoming and most helpful. We have also stayed at Bali on Ann Street and although smaller, still is great!!
February 1, 2020 - Website

Ann Street 2 a home away

by Recent Guest
Our second year in this cottage and we know we will be back. Lovely and spacious, this cottage feels like home and has everything needed for your stay. Close to Duval but closed in and peppered with the tropics you enjoy the pool and the quiet. Joyce our agent is welcoming and most helpful. We have also stayed at Bali on Ann Street and although smaller, still is great!!
February 1, 2020 - Website

Schroder's review

by Glenn S.
Great location. Right in the thick of the action, but a little quiet oasis to yourself. Best of both worlds. Parking was a *****. Glad we lucked out by finding a spot a few streets away but it was only by luck. Place was clean and relaxing. Pool was nice also. Great stay!
February 1, 2020 - Website

Great location & property

by Recent Guest
Cottage location was perfect and loved the pool and privacy. The cottage was very clean and brightly decorated as shown. The bathrooms and kitchen were outdated, but also very clean. The location couldn't be any better within walking distance to just about everything and 1.5 blocks from the free Duval Loop shuttle bus. If there was one drawback, it would be the bathrooms age. If I was the owner I would update them.
January 1, 2020 - Website

Loved Ann St. Cottage

by Connie S.
Loved Ann St. Cottage and look forward to my next stay. Location is perfect along with privacy. Well decorated, clean and very comfortable. Rent KW was very attentive to one maintenance issue. The only drawback is no parking space.
January 1, 2020 - Website

Loved Ann St. Cottage

by Movita S.
Loved Ann St. Cottage and look forward to my next stay. Location is perfect along with privacy. Well decorated, clean and very comfortable. Rent KW was very attentive to one maintenance issue. The only drawback is no parking space.
January 1, 2020 - Website

PERFECT LOCATION!

by Recent Guest
This rental is located within a few steps to Duval Street, The harbor, marina, tours, shops, stores, restaurants, etc. So close yet such a quiet, lovely retreat tucked away in a beautiful garden with a nice heated pool. Very clean. Management is friendly and very responsive.
November 1, 2019 - Website

Wonderful location

by Recent Guest
Wonderful location. Very clean. Management very helpful.
November 1, 2019 - Website

Charming house in a perfect location

by Yann L.
We had a lovely stay. Not only a perfect location - just a few steps from Duval street , the harbour and all the restaurants - but also a beautiful, cosy and comfortable space with all amenities we could need. An excellent choice that we would certainly recommend. Thank you so much !
October 1, 2019 - Website

Ann St Cottage

by Joel K.
We loved the locaton. Easy to walk and bike to beaches, marinas and Duval St.
October 1, 2019 - Website

Paradise!

by James W.
Awesome location, awesome rental agency, awesome all around!
September 1, 2019 - Website

Fantastic hideaway close to everything!

by Kathy B.
This is a great property for couples. Walking or biking distance to everything. We didn’t even rent a car. Cottage is adorable, clean and perfect size for two. Rental company was very accommodating with our check out time allowing us to extend a few hours based on our flight departure time. I can’t wait to go back!!!Manager's ResponseThank you for sharing feedback from your stay with us. We appreciate your kind words and are happy that you enjoyed the cottage!
Thank you for sharing feedback from your stay with us. We appreciate your kind words and are happy that you enjoyed the cottage!
August 1, 2019 - Website

St. Ann Street

by Joe S.
FANTASTIC!!!!!!!!!!!!!
June 1, 2019 - Website

Quiet Compound

by Lorrie D.
We have been to Key West many times and never knew these cottages were tucked away here. It is a nice quiet location. The only improvement that could be made would be a washer and dryer in the unit. Manager's ResponseThank you for staying with us and taking the time to review our property. We appreciate the 5 star review! This cottage has the extra half bath rather than a washer and dryer in the unit, but there is the coin operated washer and dryer on site at Ann Street. We are very happy that you enjoyed your stay and hope to see you again!
Thank you for staying with us and taking the time to review our property. We appreciate the 5 star review! This cottage has the extra half bath rather than a washer and dryer in the unit, but there is the coin operated washer and dryer on site at Ann Street. We are very happy that you enjoyed your stay and hope to see you again!
May 1, 2019 - Website

Great Stay on Ann St.

by Recent Guest
Our lodging at Ann St Cottage was perfect for us. The location was fantastic - in the middle of everything but still quiet. We were able to park our car on Ann St (kind of lucky) and it stayed there all week as we walked to all of our activities and dining. The cottage was clean and well furnished and had everything we needed. I would highly recommend Ann St Cottage, except for the week we plan to come back. 🙂
May 1, 2019 - Website

Great Stay on Ann St.

by Michael D.
Our lodging at Ann St Cottage was perfect for us. The location was fantastic - in the middle of everything but still quiet. We were able to park our car on Ann St (kind of lucky) and it stayed there all week as we walked to all of our activities and dining. The cottage was clean and well furnished and had everything we needed. I would highly recommend Ann St Cottage, except for the week we plan to come back. 🙂
February 1, 2019 - Website

Ann Street.

by James and Patricia C.
We love this compound. It’s our fourth year and each year is better. Close to everything yet quiet and very private. Beautiful grounds and a lovely pool. Thanks Joyce and Jann. We will see you again next year
February 1, 2019 - Website

Ann Street.

by James C.
We love this compound. It’s our fourth year and each year is better. Close to everything yet quiet and very private. Beautiful grounds and a lovely pool. Thanks Joyce and Jann. We will see you again next year
February 1, 2019 - Website

Ann Street.

by Recent Guest
We love this compound. It’s our fourth year and each year is better. Close to everything yet quiet and very private. Beautiful grounds and a lovely pool. Thanks Joyce and Jann. We will see you again next year
February 1, 2019 - Website

Top Notch!

by Recent Guest
This rental was a perfect location! Close to the north end of Duval, everything was just a short walk away! The unit was bright and clean and perfect for a romantic getaway! Would rent repeatedly! The rental company was friendly and so easy to work with!
February 1, 2019 - Website

50th birthday paradise vacation

by Joey Lynn G.
This cottage was tucked away in the heart of duval. It was an amazing retreat. It was quiet and convenient to everything. I will be booking another stay soon. The staff at rent key west was extremely helpful and gave us all the resources we needed. I couldn't ask for anything more than the best!
December 1, 2018 - Website

Great Rental Property and Service

by Recent Guest
What a wonderful rental property! Location was awesome! Perfect size and fantastic staff and service.
November 1, 2018 - Website

Hidden Gem

by Recent Guest
What you see is what you get. Amazing location but so private and quiet.
November 1, 2018 - Website

Private Perfection

by Valerie D.
We absolutely loved Ann Street Cottage. SO close to the fun of Duval Street and the sunset at Mallory Square, but so quiet and secluded. We didn't see anyone in the complex other than someone cleaning the pool. The cottage had everything we needed!! We were in town to see the Avett Brothers in concert at the ampitheater and there were even folding chairs for us to use! I will absolutely stay there again and highly recommend it to any couple just needing a getaway like we did!!
October 1, 2018 - Website

Ann Street

by Richard M.
We have stayed at this property twice and there are some maintenance issues that have not been addressed. Sink facet is loose, towel rack falls off, air conditioner malfunctioned and pool is not cleaned of leaves. Overall the property is a nice place to stay.
August 1, 2018 - Website

Great Place to Stay

by John Y.
We have stayed at the Ann Street Cottage several times over the years. It is in a great location, close to just about everything. It feels like home to us. Comfortable bed, well stocked full kitchen, two bathrooms, and several little things that make the stay enjoyable. Although it is very close to all the action on Duval Street, it is quiet inside the compound. We highly recommend this quaint little cottage.
May 1, 2018 - Website

It was the perfect place

by Kathleen p.
Stayed x 14 days, clean, cute, half bath was major plus as was the King bed....dont see many King sized beds. Private patio. Very quiet. Tucked away in gardens and behind cute, locked picket fence. We saw a total of 5/6 people on the property the entire 2 weeks. Walking/biking distance to everything Manager's ResponseThank you for your wonderful review! We are very happy to hear that you enjoyed your stay at the cottage. We look forward to seeing you again!
Thank you for your wonderful review! We are very happy to hear that you enjoyed your stay at the cottage. We look forward to seeing you again!
April 1, 2018 - Website

April stay at 21902 Anne AStreet

by Robert T.
Outstanding! The entire process, from reservation, to check-in, to staying in the cottage, were exceptional. The location is close to everything but we still felt distant from the noise when we wanted to be.
March 1, 2018 - Website

KW is all heaven

by Judith G.
small, private, well equipped, 1 br cottage
March 1, 2018 - Website

KW is all heaven

by judith g.
small, private, well equipped, 1 br cottage
March 1, 2018 - Website

Ann St Cottage

by Gia S.
This place was perfect for my husband and myself! Size of the place is perfect for 1 or 2 people. Well maintained. Private pool shared by the other 3 adjoining cottages. But we were lucky to have the pool all to ourselves! The location could not have been more perfect as well. Will definitely stay here again.
March 1, 2018 - Website

Key West

by Wendy M.
The cottage was great, clean and quiet, 2 bathrooms, lovely little private patio.
February 1, 2018 - Website

Ann Street Cottage in late February, early March

by Michael N.
Ann Street cottage was perfect and better than expected. Location could not have been more convenient. Manager provided good customer service. We highly reccomend this cottage.
February 1, 2018 - Website

Ann St. Cottage

by John K.
We loved Ann St Cottage and will recommend to all our friends. Bathroom needs some minor repairs (woodwork beginning to rot from moisture), other than that bathroom was very clean. Theres a shared patio between properties, drapes on door leading to the patio would be nice as there is a direct line of sight into adjacent unit while sitting in Anne Sts living room.
January 1, 2018 - Website

A Gem of a Hideaway so Convenient to Everything!

by Patricia Z.
A perfect little cottage in an over-the-top tropical garden and one block from all the action of Duval Street. What more can one hope for on a Key West vacation? The cottage was impeccable; clean, well appointed, and nicely decorated. The unheated pool was lovely to look at but too cold to go swimming. (The only negative about the place:( ) We had a wonderful time and would definitely return to that little bit of heaven!
October 1, 2017 - Website

Great stay

by Nick K.
My wife and I stayed at Ann Cottage for a week. The accommodations were bright, clean, and very close to Duval Street. The bed was very comfortable as was the living room. The grounds outside the unit were lush and the pool was very close.
May 1, 2017 - Website

Great location

by Rose H.
Very nice place in a great location. Very secluded but close to everything. We walked everywhere.
April 1, 2017 - Website

Cottage in paradise

by Recent Guest
The pictures are exactly what you experience. The location was the best, your around everything you need. I would definitely go back.
April 1, 2017 - Website

Bucket List Trip

by Rickey P.
Close to down town Deval and watch the sun set.
March 1, 2017 - Website

Delightful cottage

by Bryn E.
We absolutely loved our stay at Ann Street Cottage. The property was exactly as shown in the photos. It was spotless, comfortable and so much attention to detail which made our holiday stay a pleasure. The location is central to everything and yet away from the madding crowd. Air conditioner was very quiet and effective. Tropical garden and pool was a delight....couldn't fault the place. Rent Key West Vacations were a pleasure to deal with and I would highly recommend this company.
March 1, 2017 - Website

First time Key West trip

by Tina W.
Loved the location of Ann Street Cottage. Close to all the action, but quiet and private. Very secure feeling. Grounds were beautiful. Cottage was so cute. The only complaint would be the mattress. Definitely needs replacing. We rented a car on our trip and learned that parking can be very difficult. Next time, we will not be renting a car as everything is within walking distance of the cottage.
February 1, 2017 - Website

Perfect getaway

by Chris S.
This turned out to be one of our most relaxing vacations ever. The property location was extremely close to all the action and many eating & drinking establishments. Due to dietary restrictions, I don't like to eat out much. The kitchen was essential! Although small (galley like), it was very well equipped for a rental property. We had no problem w/ cooking, although counter space was limited. I do find that knives in these places need to be sharpened more frequently...this one included.Management company was helpful in first couple of days to negotiate some minor issues. I probably could have handled myself, but did not want to be bothered given that I was on vacation. But all issues resolved almost immediately.Pool was nice, especially since we only saw a couple using it for the short time they were there. Basically had it to ourselves.Only thing we did not like was the enclosed patio. It seemed aittle damp and the umbrella had an algae growing on it. It just made it seem dirty. We used it only the first night, but really did not want to go out on it. Fortunately, we had the pool and could use it for our cocktail hour.Property was very secure. We brought our own bike with us and had absolutely no worries about keeping them locked up outside our unit, since the units are within the confines of a locked gate.All that was described in property listing was very accurate. We felt that the value was very fair for what we wanted.Final note, The Stoned Crab on Roosevelt Blvd and the adjoining little fish market were outstanding. Lunched on stone crabs at restaurant one afternoon, and bought the freshest fish we had ever eaten from fish mkt/stand for 6 of our dinners. Expensive....but what isn't in KW?
February 1, 2017 - Website

Anne Street Cottage

by Karl S.
Spent 10 days at Anne Street Cottage. Second time here. Great location, beautiful grounds and very quiet. Kitchen has been upgraded since last visit. Nice having 1/1/2 baths. Bright and comfortable.
February 1, 2017 - Website

Awesome hidden retreat

by David P.
So enjoyable to be located in the middle of town and yet be so secluded. Unit was very clean, well stocked and quiet. Secure entry gates and unit entry. A great time! Will be back!
November 1, 2016 - Website

Great Little Cottage

by John Y.
We have stayed at the Ann Street Cottage on earlier visits to Key West and love it. It's got a great location, close to just about everything. Despite being located in the middle of all the action, it is very quiet and private. It feels very tropical and is comfortable. We particularly like the fact that it has two bathrooms.
October 1, 2016 - Website

Anniversary Stay

by Philip F.
Rental experience was very good. Accomodations were good except not enough hangers in the closet, light wasn't working in the closet and the way they had the wall switch and the lamp switches was awkward-couldn't turn off the wall switch or the clock would go blank.
June 1, 2016 - Website

Keep this secret or it will be gone the next time I want to book

by Kathy I.
This beautiful cottage is just steps away from Sloppy Joes, in fact you can hear the band playing from the pool. When you enter the gardens you have no idea you are so close to the center of the Key West hotspots. We rented bikes, which I always recommend, but many times we ventured out on foot because everything was so close. This unit has a hidden inside patio that is hidden from view. The pictures as you see then are a perfect description of the unit. Guest before us left behind useful items such as salt, pepper, sugar, coffee, dish soap, plastic cups that look just like the cups used in the local bars, and even some tasty beverages. Our favorite spot was the pool. We almost always had it to ourselves. Most people were out touring the island and this is our 4th trip and we took it real easy. I enjoy staying in a different place for each trip to make them all unique, but next time, I will come back to this same spot, the location and privacy are ideal.
May 1, 2016 - Website

Great place for a 35th anniversary vacation

by Joe C.
We loved Ann Street cottage. It's so close to Duvall Street yet so quiet. We used the pool everyday and rarely did we have to share it. Walking distance to great restaurants, shopping and the harbor. Cottage was nicely decorated and we didn't find it lacking in any of the things that we needed. Would definitely stay here again and recommend it to our friends.
April 1, 2016 - Website

Ann Street Cottage

by Debra P.
This was our second time at Ann Street Cottage. The unit is in a great location and is very clean. We will return.
April 1, 2016 - Website

April Birthday Vacation

by John M.
We had a great time at the Ann ST cottage. The property was even better than the pictures. We will rent the cottage again!
April 1, 2016 - Website

Great location, nice accomodations

by Recent Guest
Ann Street Cottage is one block from Sloppy Joes and a couple blocks from the marina. Great place to start your days in Key West. We brought bikes and had a good place to look them up. Laundry was never crowded and easy to do. Pool was shared, but we never had a problem with too many people. The cottage "community" was quiet and nice.
February 1, 2016 - Website

Ann Street Cottage Get Away

by Recent Guest
We spent a week here in February of 2016. Previously, we stayed at Bali Hideaway which is in the same compound. Despite being a block off Duval, this compound is amazingly quiet and private. Both cottages were clean, comfortable and furnished more than adequately. We will return.
January 1, 2016 - Website

A Wonderful Retreat!

by Diane J.
We enjoyed a wonderful week in Key West, and staying at the Ann Street cottage was one of the things that made our trip so enjoyable. The cottage is beautifully decorated, is very comfortable, is in a perfect location, and yet is quiet and soothing since it is located within a lush tropical garden right in the middle of it all! I can't imagine staying anywhere else in the Keys now that we've found this wonderful retreat! Just beware that the pool isn't heated and even with unseasonably warm weather this winter, it was cold and not really suitable for swimming. It was beautiful, though, and we enjoyed poolside drinks before dinner!
December 1, 2015 - Website

Great vacation hideaway

by Randall G.
Great vacation hideaway, close to Duval Street yet hidden away if you're just looking to relax. Walking distance to everything!!
December 1, 2015 - Website

December stay

by Recent Guest
We found the whole exerience via this agency to be a very positive one. The staff was friendly, and knowledgeable. The house was clean and well equiped. The bed comfortable, stero system much appreciated, and also a friendly cat to pet! The location was outstanding, ideal even, walking access to everywhere! We would consider using this agency again!
November 1, 2015 - Website

A little slice of paradise

by Christopher M.
The Ann Street Cottage was a wonderful place to stay while we were in Key West. The location could not be better. Close to lower Duval, but off the beaten path enough to be quiet at night. It even came with a community cat!
November 1, 2015 - Website

Always a perfect place to stay...

by Linda M.
Being so close to everything in Old town is such and advantage. You are never more then a few blocks from anything you want or need to do. Accommodations are always wonderful.
October 1, 2015 - Website

Perfect cottage!

by Ric S.
Loved this cottage! Comfortable, soft bed, clean linens and dishes, nice private patio! Perfect location! We couldn't have gotten a better cottage for our wedding weekend! Thank you we will be back!!
October 1, 2015 - Website

Perfect cottage!

by Richard S.
Loved this cottage! Comfortable, soft bed, clean linens and dishes, nice private patio! Perfect location! We couldn't have gotten a better cottage for our wedding weekend! Thank you we will be back!!
October 1, 2015 - Website

Cozy cottage

by Recent Guest
The cottage was very cozy and had all the needed furnishings for a great stay! The cottage was very quiet even though it was one block off of Duval street. Excellent location to get to everything! The rental agency was always available and very helpful through out the vacation.
October 1, 2015 - Website

Cozy cottage

by Amy G.
The cottage was very cozy and had all the needed furnishings for a great stay! The cottage was very quiet even though it was one block off of Duval street. Excellent location to get to everything! The rental agency was always available and very helpful through out the vacation.
July 1, 2015 - Website

Airy, bright and comfortable

by Claudette K.
This location is perfect, one block away from Duval in old town. We went for our honeymoon and it was a perfect off-the-beaten-track location, quiet with plenty of room. Loved the bright, open layout!! Only con would be lack of parking...
May 1, 2015 - Website

Ideal Location in a Charming Cottage

by Recent Guest
We absolutely loved our honeymoon at the Ann Street Cottage. It is the perfect location - the vast majority of places we went were within a 10 minute walk. The cottage itself is adorable with a great Key West vibe. It was comfortable, clean, and the air conditioning was great. We really enjoyed the pool - it was warm but still refreshing. And we loved being greeted by the friendly, adorable cat every night! We'll definitely be back!
April 1, 2015 - Website

Wonderful Experience

by Recent Guest
We spent a week at Ann Street Cottage and had a blast. The cottage was clean and looks even better than the photos. Despite being so close to Duval Street, the property was very quiet and is it's own oasis. The property is well located for walking or riding bikes too. We are already planning our next trip back!
April 1, 2015 - Website

Great property in great location

by Recent Guest
One of the best we've stayed in. In the heart of everything but it's own oasis. Will definitely stay here again.
April 1, 2015 - Website

Perfect Paradise Retreat

by Jennifer G.
This is our 6th trip to Key West and our second time using Rent Key West. Great communication. The property was better than the pictures. Clean, nicely furnished, comfy bed,... The lush gardens add to the paradise feel. The location is the BEST!!!! Close to Historic Seaport and Mallory Square. No need for a car.
March 1, 2015 - Website

Loved Ann St cottage!

by Susan M.
Ann St Cottage is beautifully decorated and in a great location! We can't wait to return!
February 1, 2015 - Website

Key West Charm

by Kathleen L.
We had a great time in Key West! The location of the Ann Cottages was close to all the action and if not we walked to everything. Great way to get our exercise in after eating all the great food! The cottage was very quaint and light. It had everything we needed and if not grocery or CVS was very close. The pool was nice but too many leaves in it. The water was too cold to swim in. Key West is very loud with traffic and parties but the cottage was tucked back enough that we were not effected by it!Overall it was very enjoyable!
February 1, 2015 - Website

Way too much fun!!

by Keith P.
What a great vacation in the Keys for us snowbirds in Ky! The staff was more than eager to make our stay a great time. The Ann Street cottage suited us well and is all a couple would need to be just close enough to all of the best bars and eating establishments Key West has to offer but yet quiet at night and very comfortable. We parked the car and never needed it. We would highly recommend the Cottage for your next Key West vacation but not on the week we will be there next year!
February 1, 2015 - Website

Delightful!

by Amy F.
Delighted with Ann Street Cottage! Property was perfect for 1/2 people and in a fabulous,quiet location! Easy walking to almost anywhere one wants to go, but property is well secluded in a lovely quiet garden center. Cottage was in perfect condition and clean. Pool was lovely, but too cold for swimming as was the ocean water also. Easy walk to a few beaches. Definitely would recommend!
January 1, 2015 - Website

Great location, comfortable, quiet

by Recent Guest
Property was in good shape, clean and most everything worked (exception was right front burner on stove). There was plenty of hot water. Location was excellent - easy walk to grocery (Fausto's), restaurants, sunset pier. Just a block off of very busy Duval St and yet very quiet. Having 1.5 baths was very convenient. Air conditioning was very efficient. We'd definitely stay here again.
October 1, 2014 - Website

Ann Street Cottage

by Debra P.
The cottage was as described and excellently located. Key West Vacations was responsive and good to work with. I would use them in the future and would also return to the cottage.
September 1, 2014 - Website

Nice Cottage/ Good location

by Recent Guest
If you want to stay toward Sloppy Joe's area on Duval Street, then this is an excellent place to stay. It was very quiet in spite of the proximity to Duval but an easy walk to shops and the bars, stores and business on Duval.
August 1, 2014 - Website

Thank you

by Meg J.
We enjoyed our stay in the Ann St. Cottage. We loved the location and the pool. The accommadations were great.
July 1, 2014 - Website

Excellent Cottage on Ann Street

by John Y.
We have been vacationing in Key West for 30 years. We typically stay at bed and breakfast accommodations. This is the first time we tried a private cottage and we were very impressed. The Ann Street Cottage is a great little hideaway yet right down in the think of things. The compound is private and very nice. The cottage itself was great. We loved it.
June 1, 2014 - Website

50th Birthday Celebration

by Recent Guest
For my wife's 50th birthday she wanted to be in Key West and we landed at the Ann Street Cottage. What a perfect place to relax and be right in the middle of all the activities of Duvall Street. We rented a scooter and went to Ft. Zachary Taylor beach every day. This is the best beach on the island for senic and snorkeling purposes. Take water shoes as it is a bit rocky but wonderful. We were very happy with this choice. Clean, great colors, private yet in the heart of all the action.
June 1, 2014 - Website

50th Birthday Celebration

by Bradley B.
For my wife's 50th birthday she wanted to be in Key West and we landed at the Ann Street Cottage. What a perfect place to relax and be right in the middle of all the activities of Duvall Street. We rented a scooter and went to Ft. Zachary Taylor beach every day. This is the best beach on the island for senic and snorkeling purposes. Take water shoes as it is a bit rocky but wonderful. We were very happy with this choice. Clean, great colors, private yet in the heart of all the action.
May 1, 2014 - Website

Honeymoon redo

by Jessica S.
My husband and I were hoping for a honeymoon redo and since we had never been to Key West, we decided to go there. When we got to the island, our check in process was very easy. Ann Street Cottage is adorable and it looks just like the pictures online. We wish it had a bathtub, but other than that the cottage was great. The kitchen is well stocked, the bed is comfortable, and it's perfect for 2 people. We ended up not liking our stay, but it had nothing to do with our cottage. We just don't party enough for Key West and we wanted more/better beaches. We would recommend Ann Street Cottage and this rental company for sure.
May 1, 2014 - Website

Perfect Spot

by Recent Guest
The entire rental experience from beginning to end was perfect. We came in late and the after hours key pick-up was exactly where they said it would be, no issues at all. We walked in and the place is exactly as pictured online. The location couldn't be more perfect - a block from Duval, close to Mallory, close to the Marina, an electric car rental place a block away. All that close by, but it was quiet, serene, and a perfect getaway. They were flexible with us on check out time because no one had it after us. We loved everything about staying there, worth the value, easy to work with, and loved the place.
May 1, 2014 - Website

GOOD TIMES

by Mark H.
Very clean, cool, quite and best of all was the location. Will definitely stay there again.
May 1, 2014 - Website

Ann Street Cottage

by Kent S.
We booked Ann St. Cottage months in advance of the BMI Keywest Songwriter's Festival. We couldn't have been happier with Rent Key West or the property. The location was perfect for the festival. The cottage was clean, well-appointed and decorated just the way we have if it was ours. The garden walk to the secluded pool is wonderful and we almost always had the pool to ourselves. The reservation, billing, check-in/out process was effortless. We will be back!
December 1, 2013 - Website

Perfect Quiet Location

by Recent Guest
Our cottage was very quaint, clean, just needing a few updates. Grounds and pool were pretty and very clean. For being so close to Duval, it was very quiet. Would definitely come back on another visit!
October 1, 2013 - Website

Awesome location at Ann Street Cottage

by Mark A.
No better location on the island. 1/2 block off Duval, no bikes or transportation needed. Minutes from everything. This was our second trip staying at Ann Street and it is perfect!
August 1, 2013 - Website

Great cottage!

by Jennifer M.
We had a great vacation and the cottage was perfect. Great location, very secluded, loved the pool! Within walking and biking distance to everything. Would definitely stay there again and again...
August 1, 2013 - Website

Key West paradise

by Jane P.
We just loved the week that we spend there.
May 1, 2013 - Website

Perfect location - Fantastic Stay

by Tanya D.
Ann Street is the perfect location for anything and everything you might want to do. We were able to walk everywhere. Lots of restaurants and shops nearby. Very close to the waterfront and any excursions you might want to take. Rent Key West was fantastic from beginning to end. Incredibly easy to deal with. I would absolutely recommend them to anyone
May 1, 2013 - Website

Perfect location - Fantastic Stay

by Recent Guest
Ann Street is the perfect location for anything and everything you might want to do. We were able to walk everywhere. Lots of restaurants and shops nearby. Very close to the waterfront and any excursions you might want to take. Rent Key West was fantastic from beginning to end. Incredibly easy to deal with. I would absolutely recommend them to anyone
May 1, 2013 - Website

Ann Street Cottage is lovely

by Recent Guest
This was our first trip to Key West-we were there a week. There are no shortage of rental properties available in Key West-but this one was the only one that has such a lovely tranquil mature landscaping and a quiet alcove and pool when one needs a break from Duval Street. The cottage was quiet, and perfectly sized for two. It's centrally located so you can walk everywhere. The cottage also had wireless, and a laundry area next to the pool. The management was professional and efficient. The ONLY draw back was parking which was blocks away. Overall we highly recommend this cottage.
April 1, 2013 - Website

Spring Time in Key West

by Suzanne L.
My husband just returned from a week's stay at Ann Street Cottages, and wish we were still there. Everything was perfect - from the location though right in the heart of Old Town, quiet and secluded, to the coffee left in the fridge - we arrived late in the evening. We could not have asked for anything more. The cottage was spotless and spacious, having 1 and 1/2 baths was fabulous! Minnie the cat greeted me each morning, as did the little lizards and wind chimes. We rented bikes for the week, absolutely no reason for a car as the airport is 10 minutes away by cab. We would HIGHLY recommend this rental. By the way, the Thai restaurant at the end of the block is scrumptious, as was the Cuban Coffee Queen. Can't wait to come back!
January 1, 2013 - Website

We love Ann street!!

by James and Patricia C.
Love Ann street. Comfortable and close to old key west haunts We love it
January 1, 2013 - Website

We love Ann street!!

by James C.
Love Ann street. Comfortable and close to old key west haunts We love it
January 1, 2013 - Website

We love Ann street!!

by Recent Guest
Love Ann street. Comfortable and close to old key west haunts We love it
December 1, 2012 - Website

25 year KW renter

by Recent Guest
If there's a better location in KW, we have yet to find it. A perfect compound.
November 1, 2012 - Website

Second Year - we're booking soon for our third year

by Recent Guest
Great place, well equipped. QUIET as a can be and clean. Only negative is "parking" - there isn't any - so if you rent here, cab it from the airport and rent a scooter or walk! - other than that - don't hesitate its wonderful.
November 1, 2012 - Website

Best Location in Key West

by Mark P.
Whether we turned left or right out of our cottage we were close to everything we wanted to see & do during our wonderful vacation. We met wonderful friends, ate wonderful food, saw wonderful sunsets. Couldn't have been a more wonderful trip. Thank you.
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September 2022
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$584
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$648
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$495
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$479
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$465
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$475
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$580
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$565
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$490
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$476
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$469
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$579
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$497
           
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$469
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$623
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$688
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$723
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$728
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$470
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$483
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$546
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$589
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$513
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$472
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$452
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$478
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$536
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$584
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$453
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$426
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$419
     
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$472
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$455
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$525
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$541
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$463
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$447
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$438
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$484
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$512
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$526
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$507
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$490
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$487
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$430
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$480
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$504
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$519
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$450
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$421
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$409
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$444
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$552
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$578
 
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$594
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$531
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$506
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$463
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$430
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$422
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$430
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$476
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$510
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$524
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$437
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$454
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$519
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$670
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$635
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$466
         
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$465
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$585
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$719
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$679
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$732
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$473
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$407
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$414
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$373
   
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$410
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$376
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$388
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$384
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$358
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$358
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$358
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$371
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