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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

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. 

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.

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.

Duval Square Retreat

Condo
Bedrooms 2
2.5 Bathrooms

Located in the heart of Old Town, Duval Square is a charming brick-paved and tree-lined courtyard complex located at the quieter end of Duval Street. The residential units are located upstairs, while quaint shops and restaurants occupy the courtyard below.

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.

Thompson's Court

House
Bedrooms 3
2 Bathrooms

28 Day Minimum rental:  Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-style design with large doors and windows that let in the natural sunshine.  The large living area is decorated in charming vintage wallpaper and bright, tropical colors.

Ann Street Cottage

House
One Bedroom
1.5 Bathrooms

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage, a charming one bedroom cottage.

Southard Street - Queen Conch

House
Bedrooms 4
4 Bathrooms

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.

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. 

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.

Map View

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