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Key West Nightly Rentals

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Tropical Village

12 Bedrooms
9 Bathrooms
5.0000
(24 Reviews)
Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately.
Located at 706 and 708 South St - near The Southernmost Point - this nightly group unit is the perfect getaway spot for large groups of friends and family.

COTTAGE @ TROPICAL VILLAGE:...

Heron Suite

Studio
1 Bathroom
4.5833
(48 Reviews)
Part of Southernmost Sanctuary Suites

The Heron Suite is located street side with it's own porch for people watching. Get one of Ana's Cuban mixes - it just doesn't get any better! Conveniently located to the beach, Duval Street, great restaurants, Ana's for great Cuban fare and morning coffee -...

Flamingo Hideaway

1 Bedroom
1 Bathroom
4.7073
(82 Reviews)
Flamingo Hideaway is on the ground floor a spacious unit.

Historic homes dating to the late 1880s, this tropical paradise has just undergone a complete restoration with exceptional attention to details.

The original Dade County pine walls have been saved to create that unique historic feel in a...

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...

Pelican Suite

Studio
1 Bathroom
4.6842
(76 Reviews)
Part of Southernmost Suites

The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before...

Sunrise Suites - Trinidad Suite 105

2 Bedrooms
2 Bathrooms
4.6829
(82 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 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...

Poolside Retreat

1 Bedroom
1 Bathroom
4.6957
(46 Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with waterfall feature(shared...

Old Town Garden Villas

4 Bedrooms
6 Bathrooms
4.9231
(26 Reviews)
The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation.

Old Town Garden Villas is comprised of the following...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(98 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 - Saint Thomas Suite 302

2 Bedrooms
2 Bathrooms
4.8438
(64 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...

Old Town Garden Villas - Caribbean Suite

1 Bedroom
1 Bathroom
4.8833
(120 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!

The bedroom is decorated in rich tropical colors. A writing desk and chair completes the bedroom. The upstairs bath features an iridescent...

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...

Creme Brulee Getaway

Studio
1 Bathroom
4.6875
(64 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...

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...

Casa Cubana @ Duval Square R14

2 Bedrooms
2 Bathrooms
4.7397
(146 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...

Casa Havana @ Duval Square R22

2 Bedrooms
2 Bathrooms
4.6512
(86 Reviews)
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, secured parking beneath the complex and security...

Sunrise Suites - Bonaire Suite 210

2 Bedrooms
2 Bathrooms
4.6333
(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...

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...

Heron Hideaway

1 Bedroom
1 Bathroom
4.5581
(86 Reviews)
Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport.

Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details...

Curry House Room 2

Studio
1 Bathroom
4.8049
(82 Reviews)
Room 2's pale shade of colors will continually remind you that you're staying in a tropical paradise. Step out onto the semi-private veranda overlooking the pool. Sit and relax, surrounded by the tropical vegetation that abounds on this magnificent island. An oversized shower in the private...

Palm Isle

1 Bedroom
1 Bathroom
4.7209
(86 Reviews)
Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork sandwiches and homemade ice-cream at the...

Traveler's Palm

Studio
1 Bathroom
4.7429
(70 Reviews)
Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly "green unit". Your roommate, or in this case, "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio apartment comes complete with a...

Toon Hall - Tropical Village

3 Bedrooms
2 Bathrooms
4.7143
(70 Reviews)
Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the...

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