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Key Lime Calypso

2 Bedrooms
1 Bathroom
4.4
(10 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...

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...

Tradewinds

4 Bedrooms
2 Bathrooms
4.7352941176471
(34 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...

Poolside Suite

2 Bedrooms
1 Bathroom
4.6363636363636
(22 Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location.

Enjoy nearby bars, shops, and fine dining...

Shark Key Chateau

5 Bedrooms
5 Bathrooms
4.75
(4 Reviews)
Château - Merriam-Webster defines it as a "large impressive residence". This does not do the 'Shark Key Chateau' justice! Very impressive, very large, very luxurious! Set apart from any residence you have experienced. But this property does not rest on

Shark Key Chateau is 'Grande' to say the...

Pescado Penthouse On Duval

3 Bedrooms
3 Bathrooms
5
(4 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,...

Paradise Suite

1 Bedroom
1 Bathroom
4.2
(5 Reviews)
Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite.

Paradise Suite is a bi-level suite with one bedroom upstairs. The bedroom features a king bed and is decorated in rich tropical colors with local Key West hand colored...

Bay Harbor View

5 Bedrooms
3 Bathrooms
4.75
(4 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.***

a passport tucked away off of mile marker 15.

While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island.

Around the back of the...

Leeward Isle

2 Bedrooms
1 Bathroom
4.76
(25 Reviews)
One half of the group unit Tradewinds, opposite Windward Isle, the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,...

Beach House

3 Bedrooms
3 Bathrooms
The Beach House is your perfect Key West retreat. This 3 bedroom 3 bath classic conch house defines Key West's unique housing style.

Relaxing and quiet, Historic Bahama Village puts you in the perfect location for delicious restaurants and fun attractions! South Beach, Fort Zachary Taylor and...

Southern Palms

5 Bedrooms
4 Bathrooms
4.8
(15 Reviews)
Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm, Traveler's Palm, and Royal Palm which can all be booked individually.

All together, these three units have 5 separate bedrooms, 3 separate hot tubs, and share an incredibly luscious...

Great Egret Escape

2 Bedrooms
2 Bathrooms
As you enter the home through the beautiful stain-glass door, you will be greeted by colorful artwork, high ceilings and rich wooden floors. Just to your left is the immaculate kitchen, fit for a master chef! You will love the brand new appliances, marble counter tops and island, with bar seating...

Tortuga Suite #301

2 Bedrooms
2 Bathrooms
4.625
(24 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Salty Air Retreat

2 Bedrooms
1 Bathroom
3.5
(2 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...

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...

Island Oasis

2 Bedrooms
2 Bathrooms
4.7777777777778
(45 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...

Duval Corner

1 Bedroom
1 Bathroom
4.6444444444444
(45 Reviews)
With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer.

Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a...

Sky Loft

1 Bedroom
1 Bathroom
5
(6 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...

Catalina Suite #311

2 Bedrooms
2 Bathrooms
4.7021276595745
(47 Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Bermuda Suite

1 Bedroom
1 Bathroom
4.7551020408163
(49 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...

Fishtail Hideaway

1 Bedroom
2 Bathrooms
5
(3 Reviews)
Fishtail Hideaway will make you feel like you may never want to return home with its intimate, private garden from all the fun and beauty Key West has to offer.

Your living area offers a brand new, large, comfortable couch; which also serves as a sleeper sofa. Unique art hangings and decorative...

Poolside Paradise

3 Bedrooms
2 Bathrooms
4.7179487179487
(39 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...

Mary's Backyard

1 Bedroom
1 Bathroom
4.9117647058824
(34 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...

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