The Ultimate Escape: Key West Cabanas with Private Pools

Imagine this: after a late night on Duval Street, you emerge from Key West Lodge to a private pool surrounded by lush foliage. As you recline, the surface of the water glows in the Florida sun. It’s time to enjoy your oasis.

Here are some of the Key West Lodges with private pools that we now covet.

Margaret Street Retreat

This Key West cottage features a heated pool for small families, as well as ample poolside loungers for sunbathing. Place some fillet or vegetable roasts on the grill and enjoy a meal on the covered terrace. Away from the outdoors, you can take a break in the light-filled living area and enjoy the pool views.

The rental is within walking distance of the Gulf of Mexico, marinas, restaurants and shops. Some of Key West’s most popular destinations can be reached by car or bike a short distance, including the Ernest Hemingway House and Museum, Margaritaville and Duval Street. Higgs Beach and Edward B. Knight Pier are just a mile away, while Key West’s largest public beach, Smathers Beach, is just two and a half miles from your front door.

Bahamas House

With its pretty tiles and soothing waterfalls, this resort is reminiscent of a resort in the Bahamas (hence the name!). Enjoy margaritas and fun snacks on Tommy Bahama-style patio furniture and linger on loungers under swaying palm leaves.

Located just off Duval Street, this recently renovated vacation rental is within walking distance of shops, restaurants, museums and famous historic sites like the Ernest Hemingway Home & Museum. The beach is just four blocks away, perfect for vacationers looking to take advantage of Key West’s incredible snorkeling and scuba diving opportunities.

Passover Cottage

Located in the heart of Key West, this tropical reserve features a private pool and a deck surrounded by lush greenery. The tastefully furnished interiors include attractive wooden ceilings and updated bathrooms.

Stroll down Duval Street and experience the many restaurants, unique shops, and year-round celebrations on Key West’s most popular street. Visit some of the historic sights, including the Ernest Hemingway House and Museum (inhabited by kittens), the Key West Lighthouse, and the oldest House and Garden Museum. Guests of the house are just minutes away from warm waters and pristine sandy beaches.

Villa of the Setting Sun

This two-story holiday home has plenty of places to enjoy the pool: on the edge of cozy wicker furniture, or on a porch with ceiling fans.

The private location of this house is one of its best features; It is located between the two national parks of Great Egret National Park and Leuki National Park. But you’re just 18 and a half miles from Key West, where you can visit the Ernest Hemingway House and Museum and the southernmost point of the continental United States (among other attractions). You can see the area’s tranquil wildlife at the National Reef Sanctuary Nature Center and the Blue Hole Observatory, both within 15 miles.

Petronia Paradise

If you and your loved one are looking for a romantic getaway, this lovely cottage is for you. The verdant gardens and unique private pool will make you feel as if you have stepped into a tropical fairy tale.

This classic Key West residence is located in the heart of Old Town, not far from the southernmost tip of the United States. Many restaurants, sandwich shops, and local grocery stores are just a few blocks away. Visit the world-famous Duval Street, known for shopping, dining, and entertainment. Enjoy a beautiful sunset at Mallory Square or dine at one of the many restaurants on the historic harbor area’s waterfront. Be sure to visit the nearby Key West Butterfly Museum and Natural Conservatory, which are undoubtedly one of the best attractions in the area.

Sapodilla Villa

This Key West cottage is perfect for slowing down. The shaded swimming pool adjoins a unique and lush terrace area. Cool off in the pool, then relax with friends and family on the nearby deck.

It is located next to the old part of the city, where there are many shops and restaurants. Meanwhile, a few blocks to the south is the sandy beaches and warm waters of Higgs Beach.