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Key West Rentals

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Key West Nest

3 Bedrooms
2 Bathrooms
This could be your home away from home… All the comforts you’re used to right here in Key West.

The 3 bedrooms and 2 baths comfortably accommodate up to 6 persons (3 couples, etc). There is a king bed in the master bedroom and queen beds in the other two bedrooms. The kitchen is well stocked with...

Papa's Hideaway #2 - The Sun Also Rises

Studio
1 Bathroom
4.6087
(92 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,...

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...

Tsalta

3 Bedrooms
3 Bathrooms
5.0000
(4 Reviews)
At last, a magnificent 3-bedroom home in the middle of Old Town with room for all. This home is a BIG secret but not for long! Lushly landscaped grounds with meandering brick walkways leading to the main house, pool and guest cottage. New owners with new furnishings and linens, breathing new life...

Hemingway's View

3 Bedrooms
2 Bathrooms
4.6667
(126 Reviews)
One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage.

Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks...

Mary's Backyard

1 Bedroom
1 Bathroom
4.9118
(68 Reviews)
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 such as Mary's Backyard Too and Banana's Foster Guesthouse and across the street from Seaport Suite.

The location itself could not be...

Curry House Bed & Breakfast

9 Bedrooms
9 Bathrooms
5.0000
(2 Reviews)
The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as "Curry's Rooms" in the mid-1900's. Now the inn offers nine beautiful guestrooms and the commercial kitchen serves breakfast each morning by the pool. Eight of the rooms have doors onto verandas, four...

Casa Atlantic

3 Bedrooms
3 Bathrooms
This three bedroom, three bathroom home is an absolute dream! From its perfect location to the picturesque street and impeccable interior, Casa Atlantic is just what you need to enjoy an extended stay on our beautiful island.

You will enjoy strolls to the beach and to dinner at Salute and the...

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....

Passover Cottage

2 Bedrooms
2 Bathrooms
4.8657
(134 Reviews)
This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate.

This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom...

Sunrise Suites - Tierra Bomba Suite 403

2 Bedrooms
2 Bathrooms
4.3043
(46 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...

Poolside Paradise

3 Bedrooms
2 Bathrooms
4.7179
(78 Reviews)
POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE

With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living...

Sunrise Suites - Grand Turk Suite 404

2 Bedrooms
2 Bathrooms
4.6500
(80 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 - Salt Cay Suite 410

2 Bedrooms
2 Bathrooms
4.6905
(84 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...

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...

Mangrove Lagoon

2 Bedrooms
2 Bathrooms
4.9091
(22 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

In one of the most desirable locations in Key West, you will find the exquisite Mangrove Lagoon. Just walking into this pristine home will take your breath away. Featuring two bedrooms and two and a half...

Honey Bun Hideaway

Studio
1 Bathroom
4.7917
(48 Reviews)
Part of Banana's Foster Guesthouse. This cute and colorful studio is perfect for anyone who is excited to explore Key West on a budget. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at...

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...

Lazy Lane at Shipyard Condos

2 Bedrooms
1 Bathroom
4.5833
(48 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 9/4-9/15****

The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which...

Sunrise Suites - Cayo Cruz Suite 308

2 Bedrooms
2 Bathrooms
4.7632
(76 Reviews)

(Recently updated!) 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...

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...

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...

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...

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