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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...
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Island Oasis

2 Bedrooms
2 Bathrooms
4.7778
(90 Reviews)
The beaches of the Atlantic Ocean are less than a 7 minute walk away.

This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island...
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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...

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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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Sky Loft

1 Bedroom
1 Bathroom
5.0000
(12 Reviews)

This newly renovated, one bedroom, one bathroom unit comfortably sleeps four guests. From the moment you walk in, you will be amazed by the detail, decor and furnishings. The perfect rental home for those who wish to be just above all the action! You and your guests will enjoy the spacious...

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Sunset Marina View

2 Bedrooms
2 Bathrooms
Gorgeous monthly rental next to the golf course on stock island in Key West! This spacious condo is located next to the best dining and water activities the island has to offer!

When you walk into the condo, you will be fall in love with the island feel of the home. The breeze hits the palm trees...
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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...
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Sunrise Suites - Antigua Suite 312

2 Bedrooms
2 Bathrooms
4.4706
(34 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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Salty Air Retreat

2 Bedrooms
1 Bathroom
3.5000
(4 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 10/9-10/20****

This gorgeous two bedroom, one bathroom property is located in one of the most desirable areas of downtown Key West. With it's lavish walkways, on-site...
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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...
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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...
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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...
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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...

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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...
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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...
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