Searching for the perfect place to escape to this winter? With year-round sun and crystal-clear water, the Caribbean is the ideal retreat – and with frequent, affordable flights from the U.S., it’s easy to plan a last-minute getaway.  

Below, explore four of our most sought-after retreats in the Caribbean, complete with beachside settings, cooling trade winds, and stunning sunset views. An island getaway doesn’t get more idyllic.

A World-Class Beachfront Retreat in Jamaica

It’s not hard to see why Fortland’s Point was named “one of the best villas in the world” by Islands magazine. The seven-bedroom property sits on the tip of its own promontory, on the site of an old stone fort, with commanding views of the Caribbean on one side and Discovery Bay on the other. This unique location affords guests the luxury of three private beaches and top-notch snorkeling in the adjacent coral reefs. The spacious estate also includes an infinity pool, hot tub, floating bar, fitness room, private squash court, seaside putting green, and a swing set and mini tree house for the kids. And did we mention a full staff (private chef, butlers, housekeepers and more) is included in your stay? Explore Fortland’s Point >

A Contemporary-Chic Villa in St. Martin

What sets Always apart from all the other gorgeous homes in St. Martin is its impeccable modern design. Clean white interiors, open-plan living areas, and a grand staircase provide a fresh, chic backdrop to the villa’s sweeping ocean views. The six-bedroom home also boasts a large infinity pool, spacious outdoor dining and lounging areas, and a gourmet, fully equipped kitchen – plus, the beautiful beaches of Terres Basses are only minutes away. Explore Always >

A Brand-New Hillside Home in St. Barts

With three bedrooms (two with private terraces) and a clean, modern design, newly built Fleur de Cactus in St. Barts would be perfect for a group of couples or friends. Its position on a hillside affords breathtaking ocean and sunset views from nearly every room. The villa’s infinity pool appears to seamlessly blend into the sea, and the poolside gazebo is furnished with a bar and refrigerator, so guests can spend all day enjoying the phenomenal scenery. Explore Fleur de Cactus >

A Historic 11-Acre Estate in Barbados

Seven-bedroom Fustic House Private Estate was built in the early 18th century from local coral stone, then redesigned between the 1960s and 70s by the famous theatrical designer Oliver Messel. The extensive 11-acre property is beautifully landscaped with exotic gardens, a koi-filled lake, and hidden play areas, and the beach is only a five-minute walk away. The estate’s famous swimming pool is designed like a natural lagoon and fed with ionized water, making it feel as if you’re swimming in a natural spring, and the adjacent sun deck is built among the trees like a giant tree house. Fustic House also comes with its own full staff, including a professional five-star chef, a kitchen assistant, three housekeepers, and more. Explore Fustic House Private Estate >

Are you interested in a luxury villa rental in the Caribbean? Browse our selection of Caribbean villas, or contact us at 800.289.0900 to speak to a qualified villa expert who will help you explore which luxury villa best suits you.