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 King

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 King 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
June 20, 2026 - Track Survey

by Richard L

While my second stay at the Colony compound, this was my first at The Osprey #8. It was a great studio, perfect for a single. Already thinking of booking for a stay in 6-months.

We are happy to hear that you enjoyed our cottage!  We hope to have you stay with us again.

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.

Available
Unavailable
Check-In Only
Check-Out Only


September 2026
S M T W T F S
    01 02 03 04 05
06 07 08 09 10 11 12
13 14 15 16 17 18 19
$169
20
$150
21
$150
22
$150
23
$150
24
$150
25
$186
26
$188
27
$150
28
$150
29
$150
30
$157
     
October 2026
S M T W T F S
        01
$229
02
$242
03
$246
04
$213
05
$222
06
$222
07
$230
08 09 10
11 12 13
$282
14
$262
15
$307
16
$340
17
$376
18
$374
19
$393
20
$405
21 22 23 24
25 26
$304
27
$299
28
$277
29
$311
30
$332
31
$342
November 2026
S M T W T F S
01
$310
02
$309
03
$319
04 05 06 07
08 09 10
$329
11
$339
12
$379
13
$384
14
$374
15
$315
16
$299
17
$290
18
$298
19
$326
20
$348
21
$360
22
$328
23
$319
24
$322
25
$366
26
$362
27
$381
28
$356
29
$331
30
$278
         
December 2026
S M T W T F S
    01
$286
02
$301
03
$345
04
$386
05
$386
06
$333
07
$306
08
$300
09
$308
10
$347
11
$360
12
$354
13
$313
14
$293
15
$291
16
$303
17
$340
18
$406
19
$413
20
$360
21
$366
22
$369
23
$342
24
$396
25
$442
26
$494
27
$469
28
$652
29
$555
30
$715
31
$674
   
January 2027
S M T W T F S
          01
$622
02
$583
03
$510
04
$466
05
$423
06
$439
07
$486
08
$490
09
$489
10
$432
11
$416
12
$414
13
$429
14
$467
15
$545
16
$579
17
$534
18
$466
19
$467
20
$444
21
$501
22
$516
23
$525
24
$468
25
$468
26
$517
27 28 29 30
31
$478
           
February 2027
S M T W T F S
  01
$449
02
$453
03
$461
04
$509
05
$548
06
$557
07
$493
08
$463
09
$465
10
$477
11
$530
12 13
14 15 16
$541
17
$520
18
$572
19
$588
20
$576
21
$512
22
$484
23
$487
24
$505
25
$564
26
$580
27
$572
28
$510
           
March 2027
S M T W T F S
  01
$480
02
$473
03
$485
04
$541
05
$571
06
$582
07
$526
08
$526
09
$526
10
$526
11
$557
12
$571
13
$582
14
$530
15
$529
16
$531
17
$530
18
$561
19
$570
20
$569
21
$500
22
$471
23
$464
24
$482
25
$527
26
$554
27
$559
28
$500
29
$499
30
$460
31
$474
     
April 2027
S M T W T F S
        01
$515
02
$546
03
$545
04
$481
05
$456
06
$450
07
$465
08
$510
09
$536
10
$533
11
$473
12
$448
13
$446
14
$457
15
$500
16
$520
17
$522
18
$454
19
$429
20
$423
21
$434
22
$476
23
$493
24
$495
25
$444
26
$416
27
$413
28
$472
29
$505
30
$521
 
May 2027
S M T W T F S
            01
$544
02
$441
03
$383
04
$380
05
$385
06
$422
07
$439
08
$439
09
$381
10
$359
11
$370
12
$360
13
$394
14
$407
15
$406
16
$359
17
$365
18
$345
19
$364
20
$400
21
$395
22
$394
23
$353
24
$376
25
$373
26
$371
27
$369
28
$381
29
$382
30
$364
31
$362
         
June 2027
S M T W T F S
    01
$360
02
$345
03
$345
04
$364
05
$365
06
$345
07
$345
08
$345
09
$345
10
$345
11
$347
12
$351
13
$345
14
$345
15
$345
16
$345
17
$345
18
$345
19
$346
20
$345
21
$345
22
$345
23
$345
24
$345
25
$345
26
$345
27
$345
28
$345
29
$345
30
$345
     
July 2027
S M T W T F S
        01
$345
02
$345
03
$345
04
$345
05
$345
06
$345
07
$345
08
$345
09
$345
10
$345
11
$345
12
$345
13
$345
14
$345
15
$345
16
$345
17
$345
18
$345
19
$345
20
$345
21
$345
22
$345
23
$345
24
$345
25
$345
26
$345
27
$345
28
$345
29
$345
30
$345
31
$345
August 2027
S M T W T F S
01
$345
02
$345
03
$345
04
$345
05
$345
06
$345
07
$345
08
$345
09
$345
10
$345
11
$345
12
$345
13
$345
14
$381
15
$345
16
$345
17
$345
18
$345
19
$345
20
$345
21
$345
22
$345
23
$345
24
$345
25
$345
26
$345
27
$345
28
$345
29
$345
30
$345
31
$345
       
September 2027
S M T W T F S
      01
$345
02
$345
03
$345
04
$351
05
$345
06
$345
07
$345
08
$345
09
$345
10
$345
11
$345
12
$345
13
$345
14
$345
15
$345
16
$345
17
$345
18
$345
19
$345
20
$345
21
$345
22
$345
23
$345
24
$345
25
$345
26
$345
27
$345
28
$345
29
$345
30
$345
   

Book Now

Detailed Quote
Add to Favorites
Inquire
Share
Print