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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

Elizabeth Retreat

House
Bedrooms 3
2 Bathrooms

28 Day Minimum rental:  Want to saunter through the historic streets of Key West and live like a local in a quiet, Old Town residential neighborhood? Look no further than Elizabeth Retreat.

Villa Tropicale

House
Bedrooms 4
4 Bathrooms

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

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.

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.

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. 

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

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.

Pete's East 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.

Map View