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
  • Wireless Internet
  • Free wifi
  • 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

Outdoor

  • Patio or Balcony

Pool

  • Communal Pool
  • Heated Pool
LEAVE A REVIEW
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


January 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 20 21 22 23 24
25 26 27 28 29 30 31
February 2026
S M T W T F S
01 02 03
$267
04
$366
05 06 07
08 09 10 11
$305
12
$444
13
$502
14
$530
15
$407
16
$413
17
$542
18 19 20 21
22 23 24 25 26 27 28
March 2026
S M T W T F S
01
$384
02
$356
03
$383
04
$380
05
$450
06
$483
07
$495
08
$446
09
$459
10
$460
11
$451
12
$461
13
$478
14
$492
15
$455
16
$500
17
$530
18
$489
19
$483
20
$497
21
$480
22
$388
23
$347
24
$336
25
$366
26
$433
27
$466
28
$487
29
$387
30
$381
31
$354
       
April 2026
S M T W T F S
      01
$413
02
$455
03
$476
04
$462
05
$416
06
$429
07
$325
08
$366
09
$430
10
$482
11
$470
12
$368
13
$320
14
$326
15
$351
16
$413
17
$461
18
$461
19
$361
20
$314
21
$304
22 23 24 25
26 27
$294
28
$284
29
$356
30
$399
   
May 2026
S M T W T F S
          01
$453
02
$430
03
$314
04
$273
05
$264
06
$285
07
$331
08
$371
09
$370
10
$291
11
$253
12
$245
13
$265
14
$339
15
$375
16
$380
17
$281
18
$245
19
$239
20
$259
21
$317
22
$363
23
$356
24
$342
25
$313
26
$312
27
$257
28
$299
29
$330
30
$332
31
$263
           
June 2026
S M T W T F S
  01
$230
02
$235
03
$244
04
$286
05
$321
06
$323
07
$258
08
$254
09
$250
10
$248
11
$279
12
$312
13
$328
14
$251
15
$233
16
$215
17
$234
18
$276
19
$309
20
$312
21
$248
22
$232
23
$213
24
$232
25
$272
26
$309
27
$312
28
$252
29
$221
30
$216
       
July 2026
S M T W T F S
      01
$236
02
$327
03
$327
04
$327
05
$328
06
$226
07
$278
08
$277
09
$284
10
$311
11
$314
12
$250
13
$219
14
$215
15
$244
16
$274
17
$308
18
$311
19
$254
20
$222
21
$216
22
$280
23
$313
24
$330
25
$366
26
$317
27
$223
28
$254
29
$283
30
$274
31
$294
 
August 2026
S M T W T F S
            01
$294
02
$233
03
$204
04
$198
05
$216
06
$252
07
$284
08
$321
09
$273
10
$197
11
$191
12
$207
13
$241
14
$307
15
$275
16
$218
17
$192
18
$188
19
$204
20
$240
21
$272
22
$274
23
$218
24
$191
25
$187
26
$203
27
$238
28
$270
29
$272
30
$228
31
$231
         
September 2026
S M T W T F S
    01
$185
02
$202
03
$271
04
$271
05
$296
06
$270
07
$270
08
$270
09
$200
10
$236
11
$305
12
$323
13
$233
14
$206
15
$184
16
$203
17
$241
18
$276
19
$281
20
$226
21
$201
22
$198
23
$218
24
$259
25
$297
26
$304
27
$245
28
$216
29
$213
30
$235
     
October 2026
S M T W T F S
        01
$279
02
$320
03
$331
04
$265
05
$234
06
$230
07
$253
08
$299
09
$342
10
$354
11
$286
12
$249
13
$244
14
$268
15
$312
16
$531
17
$583
18
$467
19
$409
20
$402
21
$445
22
$533
23
$611
24
$619
25
$311
26
$251
27
$244
28
$267
29
$313
30
$354
31
$363
November 2026
S M T W T F S
01
$310
02
$269
03
$288
04
$409
05
$533
06
$600
07
$607
08
$517
09
$278
10
$328
11
$325
12
$328
13
$356
14
$367
15
$288
16
$247
17
$240
18
$262
19
$305
20
$347
21
$350
22
$299
23
$316
24
$310
25
$386
26
$388
27
$386
28
$384
29
$383
30
$242
         
December 2026
S M T W T F S
    01
$236
02
$289
03
$335
04
$346
05
$360
06
$301
07
$406
08
$395
09
$397
10
$399
11
$401
12
$399
13
$399
14
$240
15
$235
16
$258
17
$304
18
$350
19
$365
20
$313
21
$290
22
$316
23
$301
24
$523
25
$525
26
$526
27
$677
28
$496
29
$483
30
$622
31
$586
   
January 2027
S M T W T F S
          01
$548
02
$547
03
$356
04
$289
05
$291
06
$321
07
$387
08
$426
09
$436
10
$359
11
$304
12
$385
13
$419
14
$468
15
$584
16
$641
17
$455
18
$450
19
$470
20
$381
21
$443
22
$492
23
$477
24
$384
25
$357
26
$360
27
$396
28
$465
29
$537
30
$511
31
$452
           

Book Now

Detailed Quote
Add to Favorites
Inquire
Share
Print