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Showing 26-50 of 62 Vacation Rentals

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

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

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

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

Tropical Serenity

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

An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bungalow has been completely... 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

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

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

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

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

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

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

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

Beach Club #112

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

Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This comfortable 2 bedroom unit features a... 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

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

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

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

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

South St. Cottage

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

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... 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

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 #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

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

Beach Club #408

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

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... more

Showing 26-50 of 62 Vacation Rentals

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