10 Caribbean Getaways Where You Can Have Your Own Private Pool With a View

Villa Atabeyra luxury villa rental in St Lucia, available from ThirdHome
Photo: Courtesy of ThirdHome

Many of the islands affected by hurricanes Irma and Maria last year are making a comeback, welcoming visitors and announcing to the world that they are open for business. Jamaica is booming with standouts like Jewel Montego Bay Resort & Spa and Half Moon, while Puerto Rico is bouncing back with big names like Dorado Beach, a Ritz-Carlton Reserve that reopened this month. And those aren't the only options. You can rent your own private villa and have your own pool — with a view. For many, the word “villa” conjures images of jet-setting celebrities. But the path to your own private villa isn’t as expensive as you might think. If you have a good idea of what you’re looking for, and when, you can easily come out ahead. Do your homework, taking time to sleuth properties on Google Earth and Street View, and always use a secure payment system to ensure you don’t get scammed. For more tips on renting a villa with confidence, this guide should be a great help. If money isn’t an issue, but you aren’t sure where to start looking, allow us to present this curated list of Caribbean rentals you need to book now. In sunny Antigua and Barbuda, a stylish oceanfront villa boasts a top-level room with a sun deck. In Jamaica, you can forgo the all-inclusive scene for something much more luxurious: your own spacious villa with all the trimmings one would expect from a five-star resort. Not convinced renting a villa’s the best way to go? Villa Nonna, a five-suite manse in St. John with an infinity-style pool overlooking the ocean should help change your mind.

01 of 10

Pelican Ridge, Bethesda, Antigua and Barbuda

Pelican Ridge luxury villa rental in Barbados, available from ThirdHome
Courtesy of ThirdHome

Set on a hillside overlooking the point where Willoughby Bay meets the Caribbean, Pelican Ridge is a six-bedroom oceanfront villa straight out of a design catalog. The refined decor and spacious rooms are part of the draw, but the real star here is the centrally located pool, which boasts panoramic views of the crystal-clear sea. All bedrooms except for the master offer direct access to the pool, so you’ll feel as if you’ve got the whole place to yourself. Speaking of the master, it’s the only room with a private balcony, jacuzzi and sun terrace. Yoga, anyone? Rates from $444/night on ThirdHome.

02 of 10

The Plantation, Saint Michael, Barbados

The Plantation luxury villa rental in Barbados, available from ThirdHome
Courtesy of ThirdHome

Formerly called Anton Hall, the tastefully renovated Plantation house has all the charm of the old days without the lack of conveniences. Air conditioning, ceiling fans, cable TV and internet are included. In keeping with the Caribbean Georgian style, the eight-bedroom house features tropical touches like a low rectangular shape, sweeping verandas, and sturdy shutters. While the view from the pool will dazzle guests, the entrance hall and formal living area, done up with antiques, are perfect for hosting events. Rates from $1,000/night for main house, $1,500/night for main house and cottage.

03 of 10

Catch a Wave Bahamas, Elbow Cay, Bahamas

Catch a Wave luxury villa rental in the Bahamas, available from ThirdHome
Courtesy of ThirdHome

This six-mile-long island, part of the Abaco Islands, is as vibrant as it is quiet. You won’t find the touristy, all-inclusive crowd here, just pastel clapboard cottages, full-service marinas and resorts and beautiful beaches. This three-bedroom beach house packs the usual Caribbean amenities like Wi-Fi and A/C, as well as an outdoor grill and pool. There, you’ll find views of the Atlantic Ocean and White Sound, where the waters are as pristine as Tahiti Beach, which is just a short distance away. As if that isn’t enticing enough, the outdoor deck has its own private shower. Rates from $385/night.

04 of 10

Cobalt Villa, Blue Mountain, Turks & Caicos Islands

Cobalt Villa luxury villa rental in the Turks and Caicos, available from ThirdHome
Courtesy of ThirdHome

An emphasis on indoor-outdoor living makes this four-bedroom home a good option. An al fresco kitchen comes equipped with a grill, refrigerator, bar and sink, while an adjacent dining area encourages afternoon dips in the pool. On the second floor, a bedroom opens directly onto a patio with seating. Thanks to its prime location on the central north coast of Providenciales, Cobalt Villa also offers the best of both worlds: a private pool and easy access to the boardwalk, which leads to the beach. See rates on ThirdHome.

05 of 10

Villa Chloé, Lurin, Saint Barthélemy

Villa Chloe luxury villa rental in St Barth, available from ThirdHome
Courtesy of ThirdHome

This cozy two-bedroom villa, near the capital of Gustavia, feels like an upscale cabin. Downstairs are the common areas, with a sophisticated living room and kitchen; upstairs are the master bedrooms, with vaulted ceilings and unbeatable views. The third level has a heated plunge pool overlooking the sleepy marina. After a day of lounging, head to the main town of Gustavia for some shopping — don’t miss Les Petits Carreaux, artist Veronique Vandernoot’s whimsical outpost, or the Fish Market, where local fishermen flaunt their morning catch. Cap things off with a Latin-inspired dinner at Bonito; order the ceviche and tiraditos. Rates from $3,000/week.

06 of 10

Villa Atabeyra, Soufrière, St. Lucia

Villa Atabeyra luxury villa rental in St Lucia, available from ThirdHome
Courtesy of ThirdHome

You’ll feel worlds away from it all in this three-bedroom villa tucked away in the hillside. Just 15 minutes from historical Soufrière, it features a wide-open kitchen and colorful living space adorned with beach-inspired furniture, vaulted ceilings and wicker light fixtures. Things get even better when you step out on the veranda, which overlooks the majestic Pitons and tropical rainforest. A similarly stunning view can be had from the pool, which comes with plenty of lounge chairs for sunning. Opt for a hot stone massage at Kai Belte Spa to keep the pampering going. Rates from $440/night.

07 of 10

Casa Azure, St. Thomas, U.S. Virgin Islands

Casa Azure luxury villa rental in St Thomas, available from ThirdHome
Courtesy of ThirdHome

This three-bedroom property, overlooking Nazareth Bay on the east side of the island, is all about comfort. Each bedroom features its own en suite bathroom, while the one downstairs has its own kitchenette with a fridge for added convenience. All rooms are also equipped with air conditioning and screens. Sip a rum punch as you sun on the deck by the pool. And be sure to carve out time for a day trip to nearby St. John island, a national protected park just a quick ferry ride away. Rates from $499/night.

08 of 10

St. Thomas Luxury Villa, Misgunst, U.S. Virgin Islands

Luxury villa rental in St Thomas, available from ThirdHome
Courtesy of ThirdHome

Perched on a bluff overlooking Magen’s Bay Beach is this luxurious four-bedroom villa. The contemporary home is part of a gated community that includes an outdoor terrace filled with plants and a fountain. Inside, the renovated kitchen beckons guests to linger over Presidente beers and pate. Outside, the pool makes a statement with dramatic views of the ocean. Nearly every level has seating for small groups of guests, making this a good place for entertaining. For those who crave more privacy, the three master suites have their own balconies or terraces. Rates from $975/night.

09 of 10

Wheel House Villa, Sandy Bay, Jamaica

Wheelhouse luxury villa rental in Jamaica, available from ThirdHome
Courtesy of ThirdHome

The Wheel House Villa is part of the Tryall Club, a 2,220 acre Jamaican resort. Tennis courts and the gym are a short stroll away, and a golf cart can ferry you down to the golf course. All six bedrooms are air conditioned — the better to combat the island’s sweltering heat — and come with king-size beds, walk-in closets and marble and granite bathrooms. You’ll also love the private verandas from which you can soak in the postcard-perfect surroundings. To ensure you never go without, the full-service staff includes a cook, housekeeper, pool cleaner and gardener. Guests can even have groceries delivered. Rates from $7,000/week.

10 of 10

Villa Nonna, St. John, U.S. Virgin Islands

Villa Nonna luxury villa rental in St John, available from ThirdHome
Courtesy of ThirdHome

You’ll feel like royalty in this secluded villa with a Spanish tile roof. All five suites have ocean views, and the home is centered around the pool. You’ll find yourself spending most of your time there, as it arguably has the best view. A stone wall with a tropical backdrop looks onto an outdoor seating area, and there’s also a hot tub and pool table. French doors lead to the gourmet kitchen, where just beyond the massive living room is outfitted with sumptuous sofas and sky-high ceilings. See rates on ThirdHome.

Was this page helpful?
Related Articles