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Showing 26-49 of 49 Vacation Rentals

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

Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away... more

Cottage 2 BR 2 BA Sleeps 4

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

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

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

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

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

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 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

Casa Atlantica One Bedroom

Key West, Florida, United States

Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled with a mixture of custom made furnishings and unusual objects from all parts of the globe, this... more

Condo 1 BR 1 BA Sleeps 2

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

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

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

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

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 #103

Key West, Florida, United States

Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom unit features a large oceanfront balcony accessed from both the living/dining area and master bedroom. The unit features central heat/air, WIFI, cable TV, washer/dryer, well... 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

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

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

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

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

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

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

Showing 26-49 of 49 Vacation Rentals

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