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Bahama House

3 Bedrooms
3 Bathrooms
4.8182
(44 Reviews)
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable 3 bedroom home includes 2 bedrooms in the main house and an additional mother-in-law suite by the pool. Each bedroom features...

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...

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...

Howe Street Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(5 Reviews)

The neighborhood is complete with conch style homes, little lanes, corner gardens and yes our famous Key West Roosters watching their chicks. Featuring a classic front porch for greeting the neighbors as they go about their day. Entering into this lovely home you are surrounded with light,...

Sunrise Suites - Tahiti Suite 104

2 Bedrooms
2 Bathrooms
4.6000
(5 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Casa Caribe @ Duval Square R9

2 Bedrooms
2 Bathrooms
4.7895
(57 Reviews)
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street.

Lush and tropical gardens surround this beautiful...

Seashore at the Shipyard

2 Bedrooms
1 Bathroom
4.7778
(18 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 8/28-9/1****

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

Sunrise Suites - Bonaire Suite 210

2 Bedrooms
2 Bathrooms
4.6333
(30 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Sunrise Suites - Grand Cayman Suite 309

2 Bedrooms
2 Bathrooms
4.5556
(45 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Sunrise Suites - Saint Thomas Suite 302

2 Bedrooms
2 Bathrooms
4.8438
(32 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Almost Southernmost Retreat

5 Bedrooms
3 Bathrooms
4.8519
(27 Reviews)
Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets.

This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the...

Sunrise Suites - Cristobal Suite 411

2 Bedrooms
2 Bathrooms
4.6591
(44 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Garden of Roses

3 Bedrooms
2 Bathrooms

Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably). Stroll to shopping, entertainment, and beaches, all within a few blocks of this rental....

Atlantic Ocean View

2 Bedrooms
2 Bathrooms
*** POOL WILL BE CLOSED SEPT 5 - OCT 20****

New King-sized bed w/ pillow top mattress installed June 2015

Outside the front of the complex are the tennis courts. If you choose to stay inside the complex you can enjoy the lush landscape on the inside of the courtyard. Just a short stroll takes you...

Sunrise Suites - Grand Turk Suite 404

2 Bedrooms
2 Bathrooms
4.6500
(40 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

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...

Tradewinds

4 Bedrooms
2 Bathrooms
4.7353
(34 Reviews)
Tradewinds is comprised of the Leeward Isle and Windward Isle

Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(49 Reviews)
Truman at Duval - if you're looking for South Beach slick-- not here!

If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people...

Sunrise Suites - Cozumel Suite 112

2 Bedrooms
2 Bathrooms
4.6667
(30 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Island Oasis

2 Bedrooms
2 Bathrooms
4.7778
(45 Reviews)
The beaches of the Atlantic Ocean are less than a 7 minute walk away.

This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island...

Windward Isle

2 Bedrooms
1 Bathroom
4.6000
(35 Reviews)
One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design.

The Webster Dictionary dates windward back to 1549; defined as, the side or...

Duval Delight

1 Bedroom
1 Bathroom
4.8246
(57 Reviews)
Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen...

Creme Brulee Getaway

Studio
1 Bathroom
4.6875
(32 Reviews)
Part of Banana's Foster Guest House

This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with...

Secret Garden

2 Bedrooms
1 Bathroom
4.7500
(20 Reviews)
Granite counter tops are in the well outfitted kitchen. The bath has travertine on the floors and walls- its small but very attractive with a bath/ shower combination. This great location, together with interiors by one of Key West's favorite designers and its exquisite deck surrounded by palms and...

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