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Showing 1-25 of 49 Vacation Rentals

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

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

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

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

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

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

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

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

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

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

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

2 Master suites each with a king bed, The 3rd bedroom has 2 twin beds and there is a queen sleeper sofa in the living room. Large private balcony opens off of all the rooms.... more

Condo 3 BR 3 BA Sleeps 8

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

Townhomes on Windsor #3

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

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

La Brisa 405E Sea Orchid

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 2 BR 2 BA Sleeps 4

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

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

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

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

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

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

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

Southard Queen Conch Suite

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 (when rented as a two bedroom the pool is shared with the... more

House 2 BR 2 BA Sleeps 6

Coral Bay Resort - Beautiful Beachfront 2BR Condo

Islamorada, Florida, United States

This spacious condo features a king bedroom and double queen bedroom, full kitchen, living/dining combo.... more

Condo 2 BR 2 BA Sleeps 6

Showing 1-25 of 49 Vacation Rentals

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