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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

Vista Fresco

Condo
Bedrooms 2
2 Bathrooms

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst friendly neighbors. The 1800 Atlantic complex sits on 400 feet of oceanfront property.

Townhomes on Windsor #6

House
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.

Colony Calypso

House
One Bedroom
One Bathroom

This newly renovated unit is located just two blocks from world famous Duval Street and is surrounded by lush, mature coconut palms and bright, blooming bougainvilleas.  This charming one bedroom bungalow is a true island hideaway.

La Brisa #206E - Brisa Del Mar

Condo
Bedrooms 2
2 Bathrooms

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

Colony Poolside

House
One Bedroom
One Bathroom
Colony Poolside is a charming one bedroom bungalow located near the Historic Key West cemetery. This one level cottage has an open living/dining area, full kitchen and spacious bedroom with king size bed. Located on a compound with a large shared pool.

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.

Packer Retreat

House
Bedrooms 3
3.5 Bathrooms

30 DAY MINIMUM RENTAL. Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district.

Map View

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