You are here

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 #304

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 as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo.

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.

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.

Beach Club #204

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.  

Havana Lane

House
Bedrooms 2
2 Bathrooms

Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends.

Duval Square Courtyard Condo

Condo
Bedrooms 3
2 Bathrooms

In the heart of Old Town and convenient to just about everything, this condo is set above a quaint brick and tree-lined courtyard that includes shops and restaurants. This three bedroom, two bath unit is in one of the only "stand-alone" buildings in the Duval Square complex.

Reynold's Retreat

House
Bedrooms 3
3 Bathrooms

28 Day Minimum rental:  Reynolds Retreat is quintessential Key West living.  Located just a few blocks off Duval Street, Reynolds Retreat is a delightful cottage filled with historic charm and modern convenience.

Villa Tropicale

House
Bedrooms 4
4 Bathrooms

Tropical seclusion best describes this oasis in the quiet, residential area known as the Casa Marina District.

Beach Club #408

Condo
Bedrooms 4
3 Bathrooms

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 it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths.

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.

Map View