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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

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.

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.

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.  

Townhomes on Windsor #5

Villa
Bedrooms 3
3.5 Bathrooms

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft.

Southard Queen Conch Suite

House
Bedrooms 2
2 Bathrooms

Southard Street Downstairs Queen Conch is a two bedroom two bathroom retreat in a house consisting of three vacation suites. Open floor plan with French doors that open to the large shared sunny pool surrounded by beautiful landscaped garden.

Newton Street Hideaway

House
One Bedroom
2 Bathrooms

28 Day Minimum Rental:  Newton Street Hideaway is located in The Meadows of Key West, a lovely, quiet and historic neighborhood known for it's tranquil tree-lined streets and classic architecture.

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.  

Canalfront Cottage

House
Bedrooms 2
One Bathroom

28 Day Minimum Rental

Open water access!

Away from the hustle and bustle of Old Town- behind the coral topped privacy fence- lies this stunning, secluded pied-a-terre overlooking the Riviera canal.

Townhomes on Windsor #4

Villa
Bedrooms 3
3.5 Bathrooms

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft.

Map View