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Key West Rentals

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Key Lime Cottage

Studio
1 Bathroom
4.6364
(66 Reviews)
Brand New to the Rental Market!


Part of
Banana's Foster Guest House

This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go...

Sweet Serenity

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

Sweet Serenity 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...

Tropical Village -Southern Cross

2 Bedrooms
2 Bathrooms
4.7826
(46 Reviews)
Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village Compound...

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...

Old Town Garden Villas - Bermuda Suite

1 Bedroom
1 Bathroom
4.7551
(98 Reviews)
Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.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!

Downstairs is a...

Havana Daydream @ Key Cove

4 Bedrooms
4 Bathrooms
Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down...

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...

Key Lime Calypso

2 Bedrooms
1 Bathroom
4.4000
(20 Reviews)
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this...

Paris Mango @ Key Cove

4 Bedrooms
4 Bathrooms
Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private heated pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down,...

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...

The Headquarters

2 Bedrooms
1 Bathroom
Walk into to The Headquarters and experience purer paradise! The living area has gorgeous, light wooden, vaulted ceilings and a plush couch that offers ultimate comfort.

Just off the kitchen, you will find a state of the art kitchen with stainless steel appliances and granite countertops. The...

Waterfall 3

Studio
1 Bathroom
4.3333
(54 Reviews)
As the name suggests, the Garden House's "Waterfall" rooms are tucked behind the tropical lagoon's waterfall... Just steps away from the breakfast and sitting area. Considering the location and price, you will not find a better deal in all of Key West

This cozy bedroom shares a bathroom with...

Sunrise Suites - Bimini Suite 211

2 Bedrooms
2 Bathrooms
4.3636
(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 many...

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...

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...

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...

Tradewinds

4 Bedrooms
2 Bathrooms
4.7353
(68 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...

Curry House Room 4

Studio
1 Bathroom
4.6000
(80 Reviews)
Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The...

Almost Southernmost

2 Bedrooms
1 Bathroom
4.6316
(76 Reviews)
This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St.

The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a King pillow top bed upstairs, another...

Hemingway's Shadow

1 Bedroom
1 Bathroom
4.6667
(6 Reviews)
Hemingway's Shadow is a well-appointed, 1 bedroom home located on Thomas Street, directly behind the Key West Lighthouse Museum.

The living room, dining area and kitchen form an L-shape open area. The kitchen also has a counter with seating for those times you don't care to use the dining table...

Tropical Village - Tropical Cottage

2 Bedrooms
2 Bathrooms
4.6364
(66 Reviews)
Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free...

Old Town Garden Villas - Andros Suite

1 Bedroom
1 Bathroom
4.8293
(82 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!

Andros Suite is a bi-level suite with a very spacious bedroom upstairs with Caribbean colors and wood floors.

Key West Vacation Rentals...

Sea Breeze

2 Bedrooms
1 Bathroom
4.7273
(110 Reviews)
Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise!

A covered porch/...

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