Key West Vacation Rentals

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2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

SIESTA BAY: Beautiful 2 bedroom 1 bath 2nd floor condo in Truman Annex, just steps away from the shared pool and a short walk to Fort Zachary Taylor State Park. Anything you want to do on our island paradise is within a few blocks. Enjoy quiet solitude in this home in between visits to chaotic Duval Street, then do it again and again.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: 2 Bedroom Condo
Area: OCEAN SIDE

BRISA DEL MAR: This 2 bedroom, 2 bath condominium is located oceanfront in a gated community with a spectacular view of the Atlantic Ocean. Walk across the street to the beach and rent umbrellas, chairs, kayaks; enjoy a sno-cone after playing volleyball or just sit on your balcony and relax in the tropical breezes with a margarita.  Now, this is livin'...


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1 Bedroom
2 Baths
Sleeps 2
Type of property: 1 Bed Home - Monthly
Area: OLD TOWN

COCONUT COTTAGE (monthly rental): Adorable, affordable, and near all the action?.... you bet! Coconut Cottage is the perfect escape for a couple or singles looking to get away from it all in paradise… Located in a quiet neighborhood of Old Town Key West, this 1 bedroom 2 bath cottage is a gorgeous spot to rest your head in our island city.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: 2 Bedroom Condo
Area: OLD TOWN

LEEWARD ISLE KEY WEST RETREAT: Dwell in the possibility! 2 bedrooms 2 baths in this newly renovated residence. From the moment you park in the private parking lot, you know you are someplace special. A small gated compound with only 13 homes, you will revel in the peace and quiet, while still being located right in the heart of Old Town.


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1 Bedroom
1½ Baths
Sleeps 4
Type of property: 1 Bedroom Home
Area: OLD TOWN

TRANQUILITY: This charming split level cottage offers 1 bedroom 1 full bath upstairs with sleeper sofa and half-bath downstairs. Cozy furnishings, soothing colors and modern conveniences make this the perfect spot for your visit to Key West. Stay in the heart of Old Town and walk to all there is to see on our island Paradise.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: 2 Bedroom Home
Area: OLD TOWN

KEY WEST GINGER HOUSE: An absolute jewel a few doors from Duval Street, this single family home is named for the breathtaking ginger plants blooming in our tropical paradise. Featuring 2 bedrooms and 2 full baths with a private jacuzzi in the garden. Soothe your muscles after a full day of partying downtown.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bed Condo - Monthly
Area: OLD TOWN

EMMA'S ESCAPE (monthly rental): Beautiful and spacious 2 bedroom 1 bath ground-level condo located in historic Old Town's Bahama Village neighborhood. Emma’s Escape is one of four condos that share the large landscaped backyard, complete with jacuzzi, pool and tiki hut. Live like a local and you will know why we call it Paradise.


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2 Bedrooms
1½ Baths
Sleeps 6
Type of property: 2 Bed Home - Monthly
Area: GOLF COURSE

A SLICE OF PARADISE (monthly rental): Imagine life in a secluded, golf community, minutes from beach, airport and local's favorite restaurants.  Two bedrooms, 1.5 bath, freshly painted, new appliances and eager to offer you a home away from home.  Located on the main thoroughfare of the exclusive Key West Golf Club, close enough to Old Town when you want it, far enough away when you don't.


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3 Bedrooms
4 Baths
Sleeps 8
Type of property: 3 Bedroom Home
Area: TRUMAN ANNEX

EASY LIVIN': The name says it all! This lovely private 3 bedroom home with pool is located in a secluded cul-de-sac in Truman Annex, a gated community located in historic Old Town Key West. Lounge by the pool in peace and tranquility or take a short walk to Duval Street where you will find the restaurants, bars, and shopping you have heard so much about.


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3 Bedrooms
3 Baths
Sleeps 8
Type of property: 3 Bedroom Condo
Area: CORAL HAMMOCK

CORAL VILLA -- Located right in the middle of the action, Coral Villa is a beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course and around the corner from many of our local favorite restaurants and marinas.  A quick 10-minute drive to Old Town, 5 minutes to Smathers Beach and the airport.


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2 Bedrooms
2 Baths
Sleeps 5
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in secluded Truman Annex. Lots of open spaces, perfect for entertaining or keeping it low-key and intimate. Easy walking distance to all Key West has to offer.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: 2 Bed Home - Monthly
Area: OLD TOWN

TRES GATOS (monthly rental): Spend a month in one of Key West's revered neighborhoods;  live like a local in this sweet 2-bedroom Conch cottage. Close to Higgs Beach, Sandy's Cafe and our infamous gourmet grocery, Fausto's Food Palace; a quick bike ride to Duval Street. Take a sunrise swim in your pool, pick up a con leche from Sandy's and your day has started in the right direction.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: 2 Bedroom Condo
Area: OCEAN SIDE

PAPAYA PLACE: This spacious 2 bedroom 2 bath condominium at 1800 Atlantic offers a wonderful relaxing view of the nature preserve next door and the ocean beyond. Well-equipped with all the modern conveniences. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing you to be lost in the tropical breezes.


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3 Bedrooms
2 Baths
Sleeps 6
Type of property: 3 Bed Home - Monthly
Area: OLD TOWN

FIRST BREATH (monthly rental): After all the hectic travel to get here, enter this lovely 3-bedroom 2-bath Conch home with pool located right in the middle of the action in Old Town Key West and take your First Breath.  Fenced in and lushly landscaped for privacy.  Walk or bike anywhere you want to go or plant yourself on the back deck at the cool and refreshing pool.  


Call For Availability and Pricing
2 Bedrooms
1½ Baths
Sleeps 5
Type of property: 2 Bedroom Condo
Area: TRUMAN ANNEX

LINGER LONGER: Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome in the President's Walk of Truman Annex, a gated community located within Old Town Key West. This property is conveniently situated poolside and just a short walk to the many restaurants, attractions and shopping that make Key West so special.


 

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