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Salt Pond Hideaway

2 Bedrooms
2 Bathrooms
4.0000
(4 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...

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...

Duval Dreamin'

2 Bedrooms
2 Bathrooms
This property is quite the hidden gem! Located on the second story of one of the most famous streets in the world, you will find Duval Dreamin'. The home over looks Duval Street and features TWO living areas, TWO bedrooms and TWO bathrooms. This is the perfect pad for couples, friends or family...

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...

Paradise on Sunset Key

2 Bedrooms
2 Bathrooms
5.0000
(2 Reviews)
Paradise at its finest is exactly what you can expect from this immaculate and unique home. Sunset Paradise is a stunning two bedroom, two and a half bathroom house on the private island of Sunset Key, in Key West. Enjoy access to private owner’s beach on western facing side of island with...

Casa Hueso

4 Bedrooms
3 Bathrooms
**There will be construction in the surrounding developing area on and off for the next year**

Trade in your stressful workdays and chilly weather for a fresh ocean breeze and plenty of sunshine! This Newly Built Key West Home has more than enough space for all your friends and family to share...

Pescado Penthouse On Duval

3 Bedrooms
3 Bathrooms
5.0000
(8 Reviews)
This 3 bed 3 bath group unit is perfect for any group looking to enjoy Key West for all it has to offer. It is comprised of the 3 units Kingfish Keep, Yellowfin Ledge, and Wahoo Way. Located on upper Duval St, this property is in the perfect location and is walking distance to Southernmost Point,...

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's Foster Guesthouse

7 Bedrooms
8 Bathrooms
4.7273
(44 Reviews)
All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on...

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...

Casa Caribe @ Duval Square

2 Bedrooms
2 Bathrooms
4.7895
(114 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...

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...

Casa 625

2 Bedrooms
2 Bathrooms
4.7500
(16 Reviews)
The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to detail! Sit on the front porch and watch the world go by or enjoy the totally private...

Eliza's Escape

4 Bedrooms
3 Bathrooms
Unwind on the wrap around patio, cool off in the pool, explore the wonders of your next vacation. Let Eliza's Escape become your favorite vacation spot!

Surprisingly elegant tropical oasis. Unassuming and hidden by lush mature foliage, in a quite Key West neighborhood. Be swept away by warm...

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...

Casa Bonita @ Duval Square R1

2 Bedrooms
2 Bathrooms
4.8000
(140 Reviews)
Short walk to Fort Zachary State Park and South Beach!

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 tropical gardens surround this beautiful development in the heart of historic Old Town. Private...

Golf Club Getaway

2 Bedrooms
1 Bathroom
Cute 2 bed 1.5 bath house located in the Key West Golf Club with fenced in yard.

New Furnishings and Appliances. Great location, steps to golf clubhouse and visitor parking, 2 miles from airport, very close to shopping, and 4 miles from Duval. Private setting with no neighbors to back, fenced yard...

Casa Diamante

3 Bedrooms
2 Bathrooms
Casa Diamante is a beautiful three bedroom, two and a half bathroom home in the perfect location of downtown Key West. This newly renovated home is sure to impress and is the perfect island getaway! When you walk through the frosted glass door, you will be welcomed by an expansive living area with...

Almost Southernmost Too

3 Bedrooms
2 Bathrooms
4.5517
(58 Reviews)
Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture with a front...

Mary's Backyard Too

2 Bedrooms
1 Bathroom
4.8333
(60 Reviews)
This 2 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 and Banana's Foster Guesthouse and across the street from Seaport Suite.

The location itself could not be better!...

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 - 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...

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