Go to Map View

Filter by:

Rental Type
Rental Location
Unit Bedrooms
Unit Bathrooms
Unit Sleeps
Activities
Amenities

Showing 21-40 of 69 Vacation Rentals

Shipyard Treasure

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

Decorated in casual contemporary style, Shipyard Treasure is centrally located in the Truman Annex, as well as within quick walking distance to all... more

Casa on Casa

Key West, Florida, United States
$8,500
1-305-296-6996
house 4 BR 3 BA Sleeps 8

So simple yet elegant, intimate yet spacious, Casa on Casa offers a unique Key West experience that will linger in your memory for years to come. As... more

cottage 2 BR 2 BA Sleeps 4

Casa MaƱana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two... more

Waterfront Two-Bedroom Suite

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

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... more

Ann Street Tranquility

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

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

Duval Roost

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

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... more

Townhomes on Windsor #4

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

Louisa House

Key West, Florida, United States
house 4 BR 4 BA Sleeps 10

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually... more

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

Showing 21-40 of 69 Vacation Rentals

stats