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Showing 1-25 of 49 Vacation Rentals

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Showing 1-25 of 49 Vacation Rentals

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