Vacations are about good weather, good company, and a good setting—ideally out in the sun. Why spend time indoors when you can do everything you’d want to out in the open air? Whether it’s eating, swimming, lounging, or even showering, these villas were built for al fresco living. From the Caribbean islands to coastal Spain, step out and enjoy nature-filled surroundings.
The Great House, Barbados
Guests at The Great House enjoy their privacy as bedrooms are spread between five structures: one main house and four chattel houses—a Barbadian term for a small moveable wooden house. That doesn’t mean the property won’t suit a group that wants to spend time together—in fact, it’s quite the opposite. Its many outdoor common areas invite a large group to congregate at any time of day. Guests are encouraged to use the villa’s 30-foot Grady White boat, manned by a boat captain waiting to take you for a gentle ride or some water skiing or wakeboarding. On the property, there is ample outdoor green space centered around a large, heated pool. Sip a cocktail on shaded lounge chairs between swims, or dry off in the sun on the lounge chairs in the grass. And the spacious backyard is flanked by indoor-outdoor living spaces on one side and the beach on the other. A covered living room provides comfortable couches and also has a bar area with high chairs to perch on while ordering your next drink. And the living area’s fourth wall remains open and leads directly to the pool. Al fresco dining is a given at The Great House: options include formal dining for 8 under a pergola; covered formal dining for 14 with serving tables; formal dining for 17 outside on the grass by the beach; and casual dining for 10 on the grass by the beach.
Masia Pairal, Barcelona
Step inside the gates of this 250-year-old Catalan Manor and feel a sense of calm take over your body. Just outside the coastal town of Sitges and 40 minutes from Barcelona, vineyards and beaches surround this classic Spanish mansion. Comfortably accommodating 24 guests, the main villa houses six bedrooms. A wing area has five more bedrooms each with patio access, including a detached cottage with a queen size bed and en-suite bathroom. The soundtrack to your stay at Masia Pairal features the songs of nearby nature and the villa’s tranquil waterfall on the lawn. The Olympic-style swimming pool is laned to inspire a friendly race, and surrounded with seating to encourage a crowd. Additional seating peppers the property’s large, gated yard, from shaded couches to a basket swing hanging from a tree branch to covered day beds. With a backyard kitchen and several large and small tables, meals can be prepared and enjoyed outside; and the outdoor living never stops thanks to an al fresco shower and sauna. Nearby to the estate, Torre del Veguer and Finca Viladellops wineries are a walk away. The villa is also close to a tennis club and world-class restaurants. The property is gated and provides parking for eight cars.
Villa Calypso, Turks and Caicos
There are countless ways for a group of friends to enjoy themselves at this Turks and Caicos gem. Providenciales’ prestigious Ocean Point neighborhood is where Villa Calypso overlooks the sparkling Sapodilla Bay. Its indoor-outdoor living areas sparkle next to the turquoise waters steps away from the door. Hang out on your private dock at water’s edge, from which you can step directly into the ocean for a refreshing swim. The home provides its guests two kayaks to explore the surroundings. In addition to the ocean, the vacation home also has its own swimming pool elevated above the dock. The surrounding seating provides endless views. Those in need of some beach time need only make the short walk to Sapodilla Bay Beach, or kayak to it directly from the property. And those that insist on staying active or injecting a little competition into their vacation will love walking over to the nearby tennis court for a match.
Martini Rose, Palm Springs
In the 1950s and 1960s, renowned American architect William Krisel and Hungarian architect Dan Palmer, helped pioneer the mid-century modern architecture style Palm Springs became known for. One of the duo’s designs—this vacation home we call Martini Rose—embodies that refined style. In particular, it’s the home’s integration with nature that is spectacular. Not only do the San Jacinto Mountains make for a majestic backdrop to this vacation home’s pristine backyard, but with an open floor plan, ample windows, and wide glass doors leading to the terrace’s flagstone floors, the home flows seamlessly from in to out in vintage Palm Springs’ fashion.
Perfect for desert-style entertaining or when you’re looking to be entertained, this property makes it easy to stay cool by taking a dip in the swimming pool or relaxing under the covered poolside lanai. Blended living spaces will also allow you to dine poolside while still shaded from the sun or watch television while enjoying a gentle breeze. And during cool desert evenings, you can warm up with a hot tub and—count ’em—three fire pits. The vacation rental was a favorite of American tenor Mario Lanza, who is said to have invited his friends Frank Sinatra and Sammy Davis Jr. over from time to time. Just like members of the Rat Pack did decades ago, today’s guests at Martini Rose can enjoy the home’s elegant design.
Diosa del Mar, Costa Rica
This Costa Rican gem is owned by two artists, so it’s no surprise that the home’s interiors are stunningly decorated with colorful art pieces and unique furnishings—for example, headboards that resemble paintings. But what makes Diosa del Mar great for outdoor living is its postcard views and movie-quality sunsets over the Pacific Ocean, among other seriously luxe amenities like daybeds, an outdoor shower, and the inclusion of a 24/7 private on-site concierge. As if the oceanfront setting wasn’t enough, the home’s 60-foot pool overlooks the beach and a large grassy yard surrounded by palm trees sets a tropical tone. Seeking white sand? Playa Blanca is just 45 steps away and is nestled in a protected cove, accessible by a private staircase climbing down the cliff’s edge. Seeking surf? Playa Negra is world-famous for its appearance in the surfing cult film Endless Summer II as well as its year-round right-hand barrel. Snorkeling gear is provided. Each of the five bedrooms has its own separate entrance, lending to additional privacy for each of its guests.