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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

South St. Cottage

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  South Street Cottage is a bright and sunny "pool home" situated on a quiet street in the coveted and quiet Casa Marina district of Key West.

La Brisa #401N Blue Heron Hideaway

Condo
Bedrooms 3
2 Bathrooms

28 Day Minimum rental:  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.

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.

Duval Square Penthouse

Condo
Bedrooms 4
4.5 Bathrooms

This huge penthouse condo, located just steps from the action of Duval Street, has been recently upgraded. This four-bedroom, 4.5 bath condo is in the heart of the action at Duval Square, a charming brick-paved and tree-lined courtyard just south of Truman Avenue.

Beach Club #112

Condo
Bedrooms 2
2 Bathrooms

Unique oceanfront living only 65 feet from the Atlantic Ocean!

The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water.  The stunning view of the turquoise water can be seen as soon as you enter the unit.  

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.

Dreaming on Duval

House
Bedrooms 5
4.5 Bathrooms

Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval!

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.

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.  

Beach Club #103

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.  

Map View