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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

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.

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.

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.

Escape on Fleming

House
Bedrooms 2
One Bathroom

28 Day Minimum Rental:  This comfortable and fresh two bedroom, one bathroom apartment is located in the heart of Old Town Key West.

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.

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.

Coconut Cabana

House
Bedrooms 3
2 Bathrooms

A quintessential "Old Town Key West" home, located in the Historic District and just one half a block off Duval Street.

Albury Bungalow

House
Bedrooms 2
2 Bathrooms

28 Day Minimum Rental:  A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one bedroom, one bathroom house also boasts a separate cottage bedroom with its own bathroom.

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.

Villa Tropicale

House
Bedrooms 4
4 Bathrooms

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

Map View

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