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Key West Vacation Rentals

Book Key West’s Best Vacation Rentals

Rent Key West Vacations manages the best Key West Vacation Rentals. For over twenty years, we’ve connected with Key West property owners and represented many of Key West’s most historic homes. On this page, you'll find properties with private pools and ocean views. Each rental is unique, so you can easily discover the right place for your group. Browse Cottages, Beach Condos, and Historic Homes at the center of Old Town Key West.

Plan Your Dream Key West Vacation!

The following results matched your search criteria.

List View

Beach Club #112

Condo
Bedrooms 2
2 Bathrooms

Unique oceanfront living only 65 feet from the Atlantic Ocean!

The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water.  The stunning view of the turquoise water can be seen as soon as you enter the unit.  

Dreaming on Duval III

House
Bedrooms 3
3.5 Bathrooms

Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval!

Beach Club #103

Condo
Bedrooms 2
2 Bathrooms

Unique oceanfront living only 65 feet from the Atlantic!

The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water.  The breathtaking view can be seen as soon as you enter the unit.  

Beach Club #104

Condo
Bedrooms 2
2 Bathrooms

Unique oceanfront living only 65 feet from the Atlantic!

The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water.  The breathtaking view can be seen as soon as you enter the unit.  

Villa Paradiso

House
Bedrooms 3
3 Bathrooms

This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It features three bedrooms and three baths.

Suite Caroline

Condo
One Bedroom
One Bathroom

28 Day Minimum rental:  Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits nestled amidst serene tropical foliage.

Southard Sophistication

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  This restoration of a majestic Key West bungalow is simply incredible. Modernists will love this property. This two bedroom, two bath home has just been completely renovated.

Cayo Hueso Cottage

House
Bedrooms 2
3 Bathrooms

28 DAY MINIMUM RENTAL

Cayo Hueso Cottage is found on a quiet street in the Heart of Old Town. Set amid plumerias and palm trees, the property is conveniently located near favorite restaurants like Mangia Mangia, Michael's, Azur, 5 Brothers and Date & Thyme.

Albury Bungalow

House
Bedrooms 2
2 Bathrooms

28 Day Minimum Rental:  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 its own bathroom.

Map View