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Showing 26-50 of 65 Vacation Rentals

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

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

Pete's Cottages

Key West, Florida, United States
cottage 4 BR 2 BA Sleeps 8

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... 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

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

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

Shipyard Palms

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

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... 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

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

condo 3 BR 3 BA Sleeps 8

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... more

Villa Paradiso

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

This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three... 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 #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

Catherine House

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

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... 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

Vista Verde

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

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 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

cottage 2 BR 2 BA Sleeps 6

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... 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

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

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

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

cottage 2 BR 2 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... more

Pete's West Cottage

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

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... more

Showing 26-50 of 65 Vacation Rentals

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