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Showing 26-50 of 66 Vacation Rentals

condo 2 BR 1 BA Sleeps 5

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... more

Waterfront Three-Bedroom Villa

Key West, Florida, United States
villa 3 BR 3 BA Sleeps 8

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... more

Beach Club #201

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 6

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,... more

Beach Club #108

Key West, Florida, United States
condo 3 BR 2 BA Sleeps 8

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... more

Casa Atlantica Studio

Key West, Florida, United States
condo 1 BA Sleeps 2

A spacious studio apartment and large deck make this the perfect romantic getaway; feast your eyes on the breathtaking views of the Atlantic Ocean.... more

Ann Street Cottage

Key West, Florida, United States
cottage 1 BR 2 BA Sleeps 4

This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.... more

Casa Atlantica One Bedroom

Key West, Florida, United States
condo 1 BR 1 BA Sleeps 2

Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled... more

Beach Club #103

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 6

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... more

Southard Queen Conch Suite

Key West, Florida, United States
house 2 BR 2 BA Sleeps 6

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation... more

Coconut Cabana

Key West, Florida, United States
house 3 BR 2 BA Sleeps 6

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... more

Albury Bungalow

Key West, Florida, United States
bungalo 2 BR 2 BA Sleeps 4

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... more

Vista Fresco

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 6

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400... more

Duval Square Castaway

Key West, Florida, United States
townome 2 BR 2 BA Sleeps 6

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... more

Beach Club #104

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 4

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... more

Villa Tropicale

Key West, Florida, United States
house 4 BR 4 BA Sleeps 8

Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down... more

Paradise Harbor Retreat

Key West, Florida, United States
townome 3 BR 4 BA Sleeps 8

Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best of Florida Keys... more

La Brisa #302E Tropical Tranquility

Key West, Florida, United States
condo 1 BR 1 BA Sleeps 2

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... more

Townhomes on Windsor #5

Key West, Florida, United States
villa 3 BR 4 BA Sleeps 6

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town... more

Newton Street Hideaway

Key West, Florida, United States
bungalo 1 BR 2 BA Sleeps 4

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... more

President's Walk

Key West, Florida, United States
house 2 BR 2 BA Sleeps 4

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... more

Colony Poolside

Key West, Florida, United States
bungalo 1 BR 1 BA Sleeps 4

Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true... more

Duval Square Retreat

Key West, Florida, United States
townome 2 BR 2 BA Sleeps 4

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... more

Townhomes on Windsor #3

Key West, Florida, United States
townome 3 BR 4 BA Sleeps 6

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town... more

Southard Street - Queen Conch

Key West, Florida, United States
house 4 BR 4 BA Sleeps 14

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation... more

Casa de Cuba

Key West, Florida, United States
cottage 3 BR 2 BA Sleeps 6

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval... more

Showing 26-50 of 66 Vacation Rentals

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