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Cabana Retreat

3 Bedrooms
3 Bathrooms
Welcome to Cabana Retreat, a newly constructed monthly rental located in the brand new Southernmost Cabana Town Home Complex.

Cabana Retreat is nothing short of pure perfection. A complete turnkey, fully accommodating monthly vacation rental is hard to come by. Located in the heart of 'Old Town...

Saint Lucia Suite #201

2 Bedrooms
2 Bathrooms
4.6842
(19 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Grand Bahama Suite #106

2 Bedrooms
2 Bathrooms
4.6538
(26 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and...

Curry House Room 1

Studio
1 Bathroom
4.7917
(48 Reviews)
Room 1 is considered by many to be one of the nicest rooms the Curry House has to offer. The recently remodeled private bathroom is spacious and includes a stunning tiled, marble shower. A semi-private veranda overlooks the pool. The veranda provides an excellent place to sit, relax & enjoy the...

Poolside Suite

2 Bedrooms
1 Bathroom
4.6364
(22 Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location.

Enjoy nearby bars, shops, and fine dining...

Saint Thomas Suite #302

2 Bedrooms
2 Bathrooms
4.8438
(32 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Shipyard Perch

2 Bedrooms
2 Bathrooms
4.6667
(21 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

The Shipyard’s Perch is a great place to stay and play near the water and Old Town Key West!

Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive...

Hispaniola Suite #101

2 Bedrooms
2 Bathrooms
4.7037
(27 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Rum Cay Suite #304

2 Bedrooms
2 Bathrooms
4.6735
(49 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Flagler's Crossing

2 Bedrooms
2 Bathrooms
Flagler's Crossing is a stunning 3 story condo with 2 bedrooms and 2 1/2 bathrooms. This home is one of the very few in Key West with a backyard ocean view! There is off-street covered parking, boat dockage, shared pool, multiple balconies, and an outdoor living area.

The backyard haven includes a...

Sweet Caroline

2 Bedrooms
2 Bathrooms
4.7027
(37 Reviews)
Part of Banana's Foster Guest House

This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front...

Salt Pond Hideaway

2 Bedrooms
2 Bathrooms
4.0000
(2 Reviews)
Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex.

It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the street. Taking a walk or bike ride down the oceanfront stretch right outside of...

Cristobal Suite #411

2 Bedrooms
2 Bathrooms
4.6591
(44 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Casa Cubana @ Duval Square R14

2 Bedrooms
2 Bathrooms
4.7397
(73 Reviews)
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West.

The foyer of this Mediterranean Style unit with Mexican Tile downstairs...

Caribbean Suite

1 Bedroom
1 Bathroom
4.8833
(60 Reviews)
Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!

The bedroom is decorated in rich tropical colors. A writing desk and chair completes the bedroom. The upstairs bath features an iridescent...

Oceana Suite

1 Bedroom
1 Bathroom
4.7143
(56 Reviews)
This immaculately clean and comfortable well air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a new Queen Sleeper Sofa with gel memory foam mattress.

The efficiency...

Papa's Hideaway #2 - Sun Also Rises

Studio
1 Bathroom
4.6087
(46 Reviews)
Papa's Hideaway was an historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value.

This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa,...

Saint Martin Suite #207

2 Bedrooms
2 Bathrooms
4.8542
(48 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and...

Caribbean Dreams

Studio
1 Bathroom
4.3000
(20 Reviews)
Caribbean Dreams is an inviting space, decorated in rich wood and cane furnishings, perfect for your Key West vacation!

Just a few steps up from the garden entry path, "Caribbean Dreams" offers a calm and cozy atmosphere. Enjoy the ultra comfy queen sized bed, free wifi, and daily housekeeping...

Abaco Suite

1 Bedroom
1 Bathroom
4.7843
(51 Reviews)
With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!

Abaco Suite, is a bi-level suite with a very spacious...

Great Exuma Suite #406

2 Bedrooms
2 Bathrooms
4.7879
(33 Reviews)
***Recently updated

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff...

Duval Square Penthouse R19

2 Bedrooms
2 Bathrooms
4.5714
(56 Reviews)
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden),
This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle.

Lush and...

Cozumel Suite #112

2 Bedrooms
2 Bathrooms
4.6667
(30 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Hibiscus Room

Studio
1 Bathroom
4.5455
(22 Reviews)
The Hibiscus is located just steps from our heated lagoon pool and adjacent to the Bougainvillea Room. Both Hibiscus and Bouganvillea share a large, semi-private deck, which has access to the front yard and the pool area.

This arrangement is perfect for couples traveling together: plenty of common...

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