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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

Casa de Cuba

House
Bedrooms 3
2 Bathrooms

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat.

Eliza's Jewel

House
Bedrooms 3
3 Bathrooms

28 Day Minimum rental:  Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West.  Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved hist

Ashe Splashe

House
Bedrooms 3
3 Bathrooms

28 DAY MINIMUM RENTAL

From the owners of South of Frances, here is another beautiful, historic restoration project. This lovingly restored home is ready for guests following a complete redo! The attention to detail and master craftsmanship can be seen everywhere in this beautiful home.

Heavenly Zen

House
Bedrooms 4
3.5 Bathrooms

Just a few blocks from Higgs Beach sits Heavenly Zen.

This four-bedroom home was recently renovated in February of 2019. Enter the home through the deep front porch— perfect for relaxing with a cocktail and chatting with the neighbors.

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.

CasaBella @ Duval Square

Condo
Bedrooms 2
2.5 Bathrooms

Located just steps from famous Duval street, this two-story town home is located in quaint, cobble stoned Duval Square. You are within the heart of the historic district and can walk almost everywhere. Although close to Duval, the home is a quiet escape from the hustle bustle.

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.

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.

Sanctuary on Simonton

Condo
Bedrooms 2.5
3 Bathrooms

28 DAY MINIMUM- Dogs allowed, with restrictions

Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect extended-stay getaway.

Map View

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