Osprey @ Colony

0 Bedrooms 1 Bathrooms Sleeps 4 Key West 481 sq. ft. Pet Friendly

Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street, just two blocks from famous Duval Street, this ground-floor studio suite is equipped to make your stay in the islands comfortable and

Studio

1 Queen

Studio

1 Sofa Bed

Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street, just two blocks from famous Duval Street, this ground-floor studio suite is equipped to make your stay in the islands comfortable and convenient. Osprey is both removed from and integrated into Old Town Key West. It is tucked away in a quiet neighborhood, but close enough to walk to any bar, restaurant, shop, or gallery. This is a non-smoking unit designed to accommodate two people.

This charming suite is comfortably furnished with a Queen bed, comfortable couch, flat-screen TV, and tropical artwork. An open floor plan creates a breezy atmosphere and the kitchenette features a coffee maker, microwave oven, stovetop, refrigerator, and the accessories to allow for small meal preparation if you aren't up for going out. A spacious bathroom with standing shower and full-length mirror completes this wonderful accommodation. The french doors lead out to an inviting deck close to the shared pool.

Kitchen

  • Stove
  • Coffee Maker - Drip
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Cooking Basics
  • Dishes & utensils for kids
  • Blender

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
  • Iron & Ironing Board
  • Private Entrance

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

Entertainment

  • Satellite or Cable
  • Television

Facility

  • Paid Parking on Premises
  • Pool
  • Street Parking
  • Shared laundry on site

Outdoor

  • Patio or Balcony

Pool

  • Communal Pool
  • Heated Pool
LEAVE A REVIEW
April 2, 2026 - Track Survey

by Donald C

The compound and the unit itself were really special. Location is important to me and this was spot on!

March 28, 2026 - Track Survey

by Troy B

Property was very nice and quiet without much street noise. The unit was a good size for our needs. Two tips to the owner - add a lamp or two and consider a new mattress. Otherwise we really enjoyed our stay at the Colony. The location is really ideal and the neighborhood is vintage Key West.

Thank you for your review! We're glad you enjoyed the quiet atmosphere, comfortable space, and ideal location in one of Key West's charming historic neighborhoods.

We appreciate your suggestions about adding more lighting and updating the mattress and will share them with the property owner for consideration.

Thank you for staying with us. We hope to welcome you back to The Colony again soon!

February 12, 2026 - Track Survey

by Walt M

After staying in one of the other units of The Colony, I expected this one (Osprey) to be similar. I was not. I would describe this unit a small efficiency apartment.

Thank you for your review and for choosing to stay with us again. We appreciate your feedback and understand that Osprey did not meet the expectations you had based on your previous stay at another unit within The Colony.

Each unit at The Colony has its own unique layout, size, and features, and we're sorry to hear that this particular property felt smaller than anticipated. We understand how expectations can be shaped by prior experiences, and we appreciate you sharing your perspective.

We're glad you gave Osprey a try, and we'd be happy to help you find a property that better matches your preferences and space requirements for a future stay. Thank you again for your valuable feedback, and we hope to have the opportunity to welcome you back to Key West.

January 3, 2026 - Track Survey

by Morgan M

I enjoy working with this company for rentals. This was our 3rd time to rent with them . However I didn’t care for this unit, it was very small, bed was not comfortable and TV was positioned poorly for watching.

Thank you for your continued trust in our company and for choosing to stay with us for the third time. We truly appreciate your loyalty and are glad to hear you've enjoyed working with our team over the years.

We're sorry to learn that this particular unit did not meet your expectations. We understand that comfort is a key part of any stay, and we're disappointed to hear that you found the space smaller than anticipated, the bed uncomfortable, and the TV placement less than ideal. Your feedback is valuable and will be shared with our team as we continually evaluate ways to improve our properties and the guest experience.

We appreciate your honest comments and hope we'll have the opportunity to welcome you back to a unit that better suits your preferences on your next visit.

September 23, 2025 - Track Survey

by Carolann S

They make it easy and fast so you can start your vacation and hit the ground running!

June 17, 2025 - Track Survey

Easy walk to everything!

by Jen J

We loved this apartment - it had all we needed to rest and relax when we were not exploring the island. The pool was perfect for cooling off from the June heat. Especially loved location for easy walk to everything!

October 15, 2024 - Track Survey

by Amy A

Very nice place and easy to access.

May 25, 2024 - Track Survey

by Eric L

We loved everything about our stay here!

April 11, 2024 - Website

Clean & Quiet

by Patricia R

The location of this property was great and it is a quiet street. The cottage was very clean and the perfect size for the two of us. We also enjoyed use of the shared pool. The bed is very high so I would like to make the suggestion of having a foot stool available for short people like me. We will definitely be back.

February 7, 2024 - Website

Great Location!

by John D

Great location! The pool was amazing! I met some wonderful friends while staying. I re-booked for next year!!!

We are excited that you have already reserved for next year. 

July 30, 2023 - Website

Great Experience

by Jenny B

I'll never stay at a hotel in Key West again after experiencing Key West Hideaways! 10x better than any crappy hotel experience on that island

March 8, 2023 - Website

Beautiful, Clean property

by DZ

Beautiful, Clean property with awesome landscapes and pool. Staff was excellent. Will be returning next year!!

Thank you!  We look forward to your return

February 25, 2023 - Website

by DQ

I use a wheelchair. Although the property is not billed as wheelchair accessible, my companion and I were able to thoroughly enjoy our stay.

We are so glad the property worked for you.  We have several properties that are close, but not totally handicap accesible, so it is nice to hear you were able to make it work.

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June 2026
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July 2026
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$213
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$269
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August 2026
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September 2026
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October 2026
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$366
November 2026
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$342
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$299
         
December 2026
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$294
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$302
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$336
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$378
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$394
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$406
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$595
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$615
   
January 2027
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$593
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$524
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$444
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$421
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$475
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$473
           
February 2027
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  01
$484
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$451
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$460
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$510
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$551
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$493
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$465
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$478
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$551
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$570
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$597
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$544
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$572
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$584
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$589
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$507
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$490
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$563
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$512
           
March 2027
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$480
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$476
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$492
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$570
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$549
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$496
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$467
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$509
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$540
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$465
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$529
     
April 2027
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$582
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$555
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$552
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$538
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$526
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$517
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$534
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$610
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$486
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$557
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$669
 
May 2027
S M T W T F S
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$641
02
$501
03
$435
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$386
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$383
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$426
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$440
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$439
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$387
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$360
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$351
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$363
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$406
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$424
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$428
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$379
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$341
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$343
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$338
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$392
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$423
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$385
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$379
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$376
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$385
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$383
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$366
31
$365
         
June 2027
S M T W T F S
    01
$315
02
$275
03
$309
04
$322
05
$323
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$282
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$259
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$259
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$259
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$294
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$307
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$318
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$280
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$251
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$245
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$254
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$287
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$298
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$371
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$298
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$263
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$254
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$266
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$291
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$311
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$306
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$258
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$261
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$251
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$259
     

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