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Splash into Summer: Homes with Swim-Up Bars

Swim up to the saloon at these estates’ spectacular in-pool tiki and cocktail bars

Is there anything better than cocktail hour by the pool? Well, yes: Cocktail hour in the pool. Popular at the world’s most exclusive resorts, the swim-up bar has found its way into some of today’s most luxurious homes. In this Luxury Defined collection, we spotlight four homes designed to enjoy in-pool cocktails. Consider a contemporary villa in the Turks and Caicos Islands with a swim-up pool bar; a rainforest retreat in Costa Rica with an in-pool tiki bar; or a waterfront jewel with a submerged cocktail bar in Grand Cayman’s biggest private pool. So swim, sip, and savor the good life.

Ultimate Oceanfront Oasis in Marathon Key, Florida

This Florida Keys estate is a tropical sanctuary with a private beach and two pools, including a seafront infinity pool and a main pool with a swim-up tiki bar, grilling area, built-in spa, and sundeck.

Ultimate Oceanfront Oasis is a unique estate in the Florida Keys. This seaside sanctuary is ideal for entertaining on a grand scale or casual relaxation. The property has a luxury resort setting with two swimming pools, 200 feet of pristine white sand beach, fruit and palm trees, numerous covered patios, and a concrete pier with deepwater dock and boat lift. The main pool has a spa and swim-up bar, and outdoor grilling kitchen under a poolside tiki bar. The second pool is a private infinity pool overlooking the sea. There are three dwellings: a custom-built main house and guest house, and a caretaker’s house, offering 12,800 square feet of air-conditioned living space with 10 bedrooms and 13 bathrooms. Further highlights include two chef’s kitchens, a nine-seat theater, two offices, an elevator, two gyms, and a seven-bay garage with abundant storage and entertainment space.

Cascade Villa in Providenciales, Turks and Caicos Islands

Cascade Villa has one of the most spectacular pools in the Turks and Caicos Islands: Below the main pool are two smaller pools: a wading pool for children and a pool for adults, complete with a swim-up bar.

Cascade Villa was designed to frame the endless water vistas from its hillside setting on Blue Mountain in Providenciales, Turks and Caicos Islands. The 9,800-square-foot, six-bedroom home by architect R.A. Shaw uses crisp angles and striking white exteriors to complement the turquoise seas. The pool is spectacular: A narrow strip of water joins Its two distinct geometric forms to access the swim-up bar. The upper pool cascades down the walls of a staircase into wading pools below. Four matching white pitched-roof gazebos provide the shade, and there is an outdoor kitchen for alfresco dining. Another staircase accesses a third deck with a large sitting area around a firepit. Steps away are the sugar white sands of Babalua Beach and the turquoise waters of Princess Alexandra National Park marine preserve.

Casa Columbo in Los Sueños, Puntarenas, Costa Rica

Casa Columbo was built into the upper rainforest to take in sweeping vistas of La Iguana golf course, Herradura Island, and the Pacific Ocean. A two-tier infinity pool overlooking a lush hillside and the sea includes a tiki bar with in-pool seating and a pool deck landscaped with tropical plants, orchids, and birds of paradise.

Casa Columbo, a tranquil, luxurious Mediterranean-style villa, is the crown jewel of Vista Tres Bahias, a private community in the Los Sueños resort on Costa Rica’s Nicoya Peninsula. The opulent 27,000-square-foot home offers 11 bedrooms and 14 bathrooms, including a lavish master suite. A two-tier infinity pool, landscaped with tropical vegetation, has a swim-up bar and sundeck. The grand entrance to the residence is a two-story foyer with double staircase, domed ceiling with crystal chandelier. Beyond are palatial reception rooms finished with handcrafted Honduran mahogany, floor-to-ceiling custom doors and windows, and high, coffered ceilings. An elevator serves all four floors, from basement to helipad (located on the roof of the six-car garage). The home is offered in turnkey condition, complete with decor, artwork, furniture, and appliances.

The Peninsula Estate in Crystal Harbor, Cayman Islands

Thoughtfully designed for elegant entertaining, this private waterfront sanctuary on Crystal Harbor, Grand Cayman, features two pool bars that complement the island's largest residential swimming pool.

The Peninsula Estate, a 1.75-acre harborfront compound on Grand Cayman Island, is an architectural masterpiece that was designed for entertaining in magnificent style. At 25,000 square feet across three levels, with six bedrooms and 10 bathrooms, the property has 21 terraces and the largest private swimming pool on the island. There is a lookout tower with sky bar and a waterfront amphitheater with seating for 24, for year-round alfresco dining. The big pool’s terrace offers a swim-up bar and a covered bar. There is a 700-bottle wine cellar, banquet-scale European-style kitchen with commercial-grade appliances and custom stone countertops, and an outdoor barbecue and entertainment space. The property also boasts tropical gardens with a 45-foot koi pond and 950 linear feet of waterfront with a 500-foot dock and an elegant boardwalk at the water’s edge.