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Showing 1-25 of 49 Vacation Rentals

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

Enjoy the extra space of a roomy three-bedroom beach house. This waterview beach house is accessed via a lushly landscaped lane and features water views from the 1st floor porch off the living area and 2nd floor balcony off the master bedroom. The... more

House 3 BR 2 BA Sleeps 8

Catherine House

Key West, Florida, United States

This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach... more

Cottage 2 BR 2 BA Sleeps 4

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

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

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

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

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

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

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

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

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

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

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

Ann Street Cottage

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 Town Hall, around the corner from Duval Street and offering 'walk to... more

Cottage 1 BR 2 BA Sleeps 4

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

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

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

Colony Poolside

Key West, Florida, United States

Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a... more

Bungalo 1 BR 1 BA Sleeps 4

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

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

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

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 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

Showing 1-25 of 49 Vacation Rentals

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