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Showing 1-25 of 47 Vacation Rentals

Pete's Cottages

Key West, Florida, United States

This property has it all! This award winning renovation offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each Twin opens to it's own... more

Cottage 4 BR 2 BA Sleeps 8

Townhomes on Windsor #5

Key West, Florida, United States

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these... more

Villa 3 BR 4 BA Sleeps 6

Louisa House

Key West, Florida, United States

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom,... more

House 4 BR 4 BA Sleeps 10

Pete's West Cottage

Key West, Florida, United States

This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each... more

Cottage 2 BR 1 BA Sleeps 4

Vista Fresco

Key West, Florida, United States

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly... more

Condo 2 BR 2 BA Sleeps 6

Paradise Harbor Retreat

Key West, Florida, United States

Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best of Florida Keys style, this spacious townhome has 3 bedrooms, 3.5 baths and is situated in a quiet Meadows... more

Town Home 3 BR 4 BA Sleeps 8

Here's Cead Mile Failte to friend and to rover. That's a greeting that's Irish as Irish can be! It means you are welcome a thousand times over wherever you come from, whosoever you may be. Welcome to our home across the pond. We know you will enjoy... more

Condo 2 BR 1 BA Sleeps 5

Casa Atlantica Studio

Key West, Florida, United States

A spacious studio apartment and large deck make this the perfect romantic getaway; feast your eyes on the breathtaking views of the Atlantic Ocean. Enjoy complete privacy, bird watching, sun and fun, located next to the White Street Pier and nestled... more

Condo 1 BA Sleeps 2

La Brisa #206E - Brisa Del Mar

Key West, Florida, United States

This unit is designed to catch the ocean breeze, with the exterior walkway leading to your front door and opening up to the view of the balcony beyond the interior. Featuring two large bedrooms and 2 baths, the interiors provide ample space for a... more

Condo 2 BR 2 BA Sleeps 6

Villa Paradiso

Key West, Florida, United States

This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft... more

House 3 BR 3 BA Sleeps 8

Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The... more

Condo 1 BR 1 BA Sleeps 4

Waterfront Three-Bedroom Villa

Key West, Florida, United States

Discover our waterfront double queen guest room with two queen beds, a white sand terrace, and water view porch. Step off your porch and feel the sand between your toes on Parrot Key's tranquil sunning terrace. Hedged by wild mangroves, along the... more

Villa 3 BR 3 BA Sleeps 8

Beach Club #112

Key West, Florida, United States

Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This comfortable 2 bedroom unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom.... more

Condo 2 BR 2 BA Sleeps 6

South St. Cottage

Key West, Florida, United States

A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large... more

Cottage 2 BR 2 BA Sleeps 6

Beach Club #201

Key West, Florida, United States

This 2 bedroom 2 bath unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom. It has central heat/air, cable TV, washer/dryer, well-equipped kitchen, 2 baths, security entry and elevator access. There is... more

Condo 2 BR 2 BA Sleeps 6

Mango Managerie

Key West, Florida, United States

Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just one block from the ever popular Cuban restaurant El Siboney and one block from the local's favorite... more

Cottage 2 BR 1 BA Sleeps 4

Vista Verde

Key West, Florida, United States

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly... more

Condo 2 BR 2 BA Sleeps 6

Albury Bungalow

Key West, Florida, United States

A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one bedroom, one bathroom house also boasts a separate cottage bedroom with it's own bathroom. Lounge on the sunny deck around the heated pool or... more

Bungalo 2 BR 2 BA Sleeps 4

Shipyard Palms

Key West, Florida, United States

In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard Condominium is great access to Zachary State Park Beach as well as the Historic Old Town Key West. This beautifully decorated first... more

Condo 2 BR 2 BA Sleeps 4

Beach Club #408

Key West, Florida, United States

Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all; from 15 foot vaulted ceilings to a well equipped kitchen, oceanfront balcony, four bedrooms... more

Condo 4 BR 3 BA Sleeps 8

Duval Square Castaway

Key West, Florida, United States

In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch,... more

Town Home 2 BR 2 BA Sleeps 6

La Brisa #302E Tropical Tranquility

Key West, Florida, United States

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South... more

Condo 1 BR 1 BA Sleeps 2

Southard Street - Queen Conch

Key West, Florida, United States

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat.... more

House 4 BR 4 BA Sleeps 14

President's Walk

Key West, Florida, United States

President’s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minutes from Fort Zachary Taylor State Park and its beach, this gated community offers lush gardens and a beautiful community pool at your doorstep. For... more

House 2 BR 2 BA Sleeps 4

Duval Roost

Key West, Florida, United States

This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a private lane. Enter the property through a secure privacy fence into the pool courtyard area. The large house towers above with high ceilings and... more

House 3 BR 4 BA Sleeps 6

Showing 1-25 of 47 Vacation Rentals

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