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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

Townhomes on Windsor #3

Villa
Bedrooms 3
3.5 Bathrooms

Once you enter this newly renovated and professionally decorated oasis…your vacation begins. This property has been created to meet your every need. The location is simply perfect: just three short blocks from Duval and tucked away on a quiet lane so you can choose your level of activity.

Louisa's Hideaway

House
Bedrooms 3
3 Bathrooms

Tucked away near the quite end of Duval Street, you'll find this stylish, newly renovated, three bedroom, three bath home.  Thoughtful details are luxuriously appointed to appeal to the traveler looking for privacy, style and elegant design.

La Brisa #403E Ocean Vista

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.

Catherine House

House
Bedrooms 2
2 Bathrooms

This charming Key West cottage is just a short walk to a selection of great restaurants, art galleries, and shopping.

Pete's West Cottage

House
Bedrooms 2
One Bathroom

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall. 

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.

Colony Sunset Suite

Condo
One Bedroom
One Bathroom

Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat.  Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art.

Shipyard Palms

Condo
Bedrooms 2
1.5 Bathrooms

In the heart of old town Key West, nestled within the secluded and lush community of private homes and condominiums of Truman Annex, this Shipyard Condominium has convenient access to both the gorgeous Fort Zachary State Park Beach and historic old town Key West. 

Villa Tropicale

House
Bedrooms 4
4 Bathrooms

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

Map View