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Duval Street Retreat

4 Bedrooms
2 Bathrooms
4.7500
(32 Reviews)
Welcome to "Duval Street Retreat" - The perfect vacation rental for large groups looking to be around all the Duval St action!

Duval St. Retreat consists of two separate two-bed, one-bath condos located at 1124 Duval St. The property is only a couple steps (or stumbles) away from fine dining, bars...

Banana Split

1 Bedroom
1 Bathroom
4.4737
(38 Reviews)
Part of
Banana's Foster Guest House

This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going...

Southernmost Retreat

2 Bedrooms
1 Bathroom
4.6591
(88 Reviews)
Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while...

Amelia House

3 Bedrooms
2 Bathrooms
4.7460
(126 Reviews)
Amelia House is surrounded by fine restaurants, art galleries, and fine shopping.

The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which...

Sunrise Suites - Grand Bahama Suite 106

2 Bedrooms
2 Bathrooms
4.6538
(52 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...

Mary's Trio

3 Bedrooms
2 Bathrooms
MARY'S TRIO is comprised of the two side by side apartment style homes named MARY'S BACKYARD and MARY'S BACKYARD TOO.

MARY'S BACKYARD:

This 1 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals...

Sunrise Suites - Barbados Suite 204

2 Bedrooms
2 Bathrooms
4.5455
(66 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...

Shark Key Chateau

5 Bedrooms
4 Bathrooms
4.7500
(8 Reviews)
Château - Merriam-Webster defines it as a "large impressive residence". This does not do the 'Shark Key Chateau' justice! Very impressive, very large, very luxurious! Set apart from any residence you have experienced. But this property does not rest on

Shark Key Chateau is 'Grande' to say the...

Caribbean Dreams

Studio
1 Bathroom
4.3000
(40 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...

Poolside Suite

2 Bedrooms
1 Bathroom
4.6364
(44 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...

Southern Comfort @ Key Cove

4 Bedrooms
3 Bathrooms
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Southern Comfort. This home is located in the private community of Key Cove Landings, on an...

Garden House Bed & Breakfast

12 Bedrooms
11 Bathrooms
Located in the heart of Old Town Key West, The Garden House Bed & Breakfast is a fantastic experience for those who want to see all that Key West has to offer. Just a few blocks from the seaport and the always exciting Dante's pool bar, and only two blocks from world famous Duval St.

Please...

Sunrise Suites - Saint Kitts 412

2 Bedrooms
2 Bathrooms
4.5294
(34 Reviews)

 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 many amenities, the specials we offer, and...

Banana Breeze @ Key Cove

4 Bedrooms
3 Bathrooms
Newly Decorated And Fully Appointed With Water View *30 NIGHT MIN STAY REQUIRED*

Look out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at "Banana Breeze" with friends, family or both while listening to island music and...

Writer's King Room

Studio
1 Bathroom
4.6190
(42 Reviews)
The Writer's King is located at the end of our second floor balcony at our Key West lodging, located directly over the Lagoon where you can listen to our gentle waterfall on cool evenings.

Featuring a King size bed with Tiffany reading lamps, the Writers' King is a relaxing way to enjoy your Key...

Hibiscus Hideaway

Studio
1 Bathroom
4.7797
(118 Reviews)
Hibiscus Hideaway is part of the group unit "4 Flowers"- located on the corner of Simonton St and Freeschool Ln, just one block from world famous Duval St.

Welcome to the perfectly located and affordable apt Hibiscus Hideaway. You will not find a better spot to spend your sunny days and exciting...

La Brisa - Beach View Breeze

2 Bedrooms
2 Bathrooms
4.5000
(8 Reviews)
Beachfront Breeze is located on S. Roosevelt Blvd., directly across from world famous Smathers Beach on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts and gardens or make your own at the pool, hot tub, saunas, under the tropical...

Four Flowers Guesthouse

4 Bedrooms
4 Bathrooms
4.8000
(30 Reviews)
Four Flowers is the perfect island getaway spot for friends and family that want to be close together while maintaining privacy. Four Flowers is a combination of 4 condos located on Simonton St - Orchid Escape, Jasmine Suite, Hibiscus Hideaway, & Gardenia Getaway

Hibiscus Suite is a queen...

Paradise Palms

2 Bedrooms
2 Bathrooms
5.0000
(2 Reviews)
Paradise Palms is located in a cute, quiet neighborhood on the edge of Old Town Key West. The exterior features of this home include one off street parking spot, a small courtyard with seating, a side deck which includes an outdoor shower and gas grill!

The master bedroom features a king-size bed...

Sunrise Suites - Cristobal Suite 411

2 Bedrooms
2 Bathrooms
4.6591
(88 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...

Bahama House

3 Bedrooms
3 Bathrooms
4.8182
(88 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...

Sunrise Suites - Cozumel Suite 112

2 Bedrooms
2 Bathrooms
4.6667
(60 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...

Seashore at the Shipyard

2 Bedrooms
1 Bathroom
4.7778
(36 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...

Papa's Hideaway

6 Bedrooms
6 Bathrooms
5.0000
(28 Reviews)
Papa's Hideaway is a Guesthouse property comprised of Garden of Eden, Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls, and Islands in the Stream. This private compound had a large outdoor gathering area around your private pool equipped with Grill, Sundeck, and Bar. Located on a...

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