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Showing 26-49 of 49 Vacation Rentals

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

Villa Tropicale

Key West, Florida, United States

Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are... more

House 4 BR 4 BA Sleeps 8

Townhomes on Windsor #4

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

Town Home 3 BR 4 BA Sleeps 6

Fabulous Conch Cottage in the Heart of the Old Town area of Key West. 2 Bedroom 2 full bath Shotgun house. This great property will accommodate up to 6 guests comfortably. Fully equipped kitchen with a full size dining table in the kitchen area. The... more

Cottage 2 BR 2 BA Sleeps 6

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

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

Beach Club #108

Key West, Florida, United States

Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This elegant 3 bedroom/ 2 bath unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom. The unit... more

Condo 3 BR 2 BA Sleeps 8

Coconut Cabana

Key West, Florida, United States

An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored... more

House 3 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

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

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

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

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

Duval Square Retreat

Key West, Florida, United States

Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The unit offers a well-... more

Town Home 2 BR 2 BA Sleeps 4

Casa de Cuba

Key West, Florida, United States

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is the historic Gato... more

Cottage 3 BR 2 BA Sleeps 6

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

Waterfront Two-Bedroom Suite

Key West, Florida, United States

Upgrade to luxury with a master king room, second queen room, living room, and water view balcony. Breathe the salt air from a beautiful two-bedroom suite overlooking the Gulf of Mexico. Relax in a spacious living room featuring a 42" flat screen TV,... more

Condo 2 BR 2 BA Sleeps 4

Ann Street Tranquility

Key West, Florida, United States

This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces. Across from the Curry Mansion and Old City Hall, around the corner from Duval Street and offering... more

Cottage 1 BR 1 BA Sleeps 2

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

Tropical Serenity

Key West, Florida, United States

An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bungalow has been completely restored to a pristine condition. A large front yard with quaint front porch give this cottage the... more

House 1 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

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

Beach Club #104

Key West, Florida, United States

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

Condo 2 BR 2 BA Sleeps 4

Newton Street Hideaway

Key West, Florida, United States

The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is... more

Bungalo 1 BR 2 BA Sleeps 4

Showing 26-49 of 49 Vacation Rentals

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