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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 #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 beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics.

La Brisa 405E Sea Orchid

Condo
Bedrooms 2
2 Bathrooms

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 and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation.

Bali Hideaway

Studio/Efficiency
Bedrooms 0.5
One Bathroom

Perfect for two, this Bali-style studio cottage has it all:  comfort, privacy and location.

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.

Townhomes on Windsor #5

Villa
Bedrooms 3
3.5 Bathrooms

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft.

La Brisa #303W

Condo
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential condominium is situated opposite the largest beach on the island, while offering the amenities of a resort hotel.

Mango Menagerie

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental: Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm.

Southard Queen Conch Suite

House
Bedrooms 2
2 Bathrooms

Southard Street Downstairs Queen Conch is a two bedroom two bathroom retreat in a house consisting of three vacation suites. Open floor plan with French doors that open to the large shared sunny pool surrounded by beautiful landscaped garden.

Map View