Key West Vacation Rentals

WiFi Access | Luxury Key West Vacation Rentals

Today's vacation rentals are becoming more and more like hotels, with a variety of amenities now available in each property to help mirror a private, luxurious hotel experience. The more amenities a property has, the better the experience for the traveler.  The majority of our vacation rentals have WIFI available and is listed under Amenities.  If WIFI is an important component necessary for a successful vacation, a quick call to Reservations can ensure you have chosen a home with WIFI access.

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Call For Availability and Pricing
2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Home
Area: Old Town

TROPICAL DREAMING: This tropical 2-bedroom home with sleeper sofa offers all the comforts of home. There are classic art features, hardwood floors, tall ceilings, and a true Key West feel. Sip a con leche on the back deck in the morning, swim and sun in the afternoon in your private pool, then head 1 block to Duval Street for the eclectic nightlife. It does not get better than this!


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3 Bedrooms
3½ Baths
Sleeps 7
Type of property: Home
Area: Old Town

BAHAMA HOUSE: Location, location, location! New and totally gorgeous, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only half a block from the fabulous shops, activities, restaurants and nightlife on Duval Street. Lounge at the pool in total privacy and solitude by day; take the walk around the corner to experience Key West nightlife.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

THE HEMINGWAY: A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. Just steps away from the community pool and only 2 blocks from famous Duval Street and historic Old Town Key West. Relax on your back porch, take a dip in the pool, and check out the sights that you have heard so much about on our Island paradise.


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2 Bedrooms
1½ Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes luxury


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Home
Area: Old Town

PERFECT PINEAPPLE (monthly rental): Long considered a sign of hospitality, the pineapple is now widely recognized as a sign of Welcome and Friendship...and so we welcome you to the Perfect Pineapple. This quaint Conch cottage, 2 bedrooms 1 bath has all the amenities for your visit, including a side yard where you can sunbathe, swim and BBQ to your heart's content.


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2 Bedrooms
1½ Baths
Sleeps 4
Type of property: Townhouse
Area: Stock Island

CORAL BREEZE (monthly rental): Imagine yourself living with the vibrant golf course greens in your backyard and cool tropical breezes wafting your way. Coral  Breeze has that and more.  Beautiful townhome with all the modern conveniences located in the exclusive gated Key West Golf Club where you can relax in the serene golf course surroundings or take a quick trip into Old Town Key West for all it has to offer.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

CONCH WIND:   Conch Wind is the property you have been hunting for! This Conch-style townhome located in Old Town Key West is nestled in a quiet, secured compound, featuring 1 bedroom with bath ensuite on the first floor and the Master bedroom with bath ensuite upstairs. A porch and second floor balcony overlook the 50 foot pool, offering lots of room for rest and relaxation.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

KEY WEST CROWN JEWEL: We know that you will enjoy staying in our little bit of Paradise. This is a 2 bedroom, 2 bath Penthouse condominium with 1350 square feet of living space. Located on the Atlantic Ocean with magnificent views from every room. A short bike ride downtown and you are in the midst of what has made Duval Street infamous: bars, restaurants, and galleries galore.


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3 Bedrooms
3 Baths
Sleeps 8
Type of property: Townhouse
Area: Stock Island

Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do. Spacious 3-bedroom townhome in the Coral Hammock gated community with pool - designer decorated.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL SEA TURTLE: This 2 bedroom 2.5 bath townhome with sleeper sofa offers comfort and space for a family of six. Conveniently located in the rooftop townhome community of Duval Square, you are close enough to the eclectic activity of Duval Street, and far enough to enjoy peace and quiet in the privacy of your own home.


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4 Bedrooms
4 Baths
Sleeps 8
Type of property: Home
Area: Old Town

BLOOM'N PARADISE: Relax in luxury in this beautiful Truman Annex private home with pool and sun deck. 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath offers room for friends and family to enjoy peace and solitude while at home, with the chaotic nightlife of downtown Key West just 2 blocks away.


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2 Bedrooms
1½ Baths
Sleeps 4
Type of property: Townhouse
Area: Stock Island

BOGEY'S RETREAT (monthly rental): Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy everything Key West has to offer in a relaxing environment.  New to the rental market and updated from top to bottom with supreme comfort in mind.  


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3 Bedrooms
2 Baths
Sleeps 6
Type of property: Home
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
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

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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