Escape the Cold: Island Villa Retreats

Beat the winter blues with a trip to Anguilla, Barbados & more tropical islands.

Over the winter? We sure are. So we’ve made a list of five villa vacations on tropical islands that make for the perfect wintertime warm-up. Leave the cold behind and get on island time - find your luxury villa rental in the sun. 

Santosha, Anguilla

When the private pool is off one deck and the beach is off another, you can’t go wrong. Relaxation rules at Santosha, a peaceful seven-bedroom beach house with al fresco dining, tennis court, and two Jacuzzis, plus an onsite staff. Bonus: For a limited time, enjoy complimentary beverages during your stay! View Santosha >  

Still Fathoms, Barbados

Vacation in style – modern, sea-inspired style – at Still Fathoms. The breezy, open living room blends into the dining terrace which blends into the beachfront garden. You and your guests can take a dip in the private plunge pool and savor meals prepared by your personal chef. And, your concierge can arrange for an array of water sports. View Still Fathoms >

Sea Salt at Tryall, Jamaica

Get the best of two island vacations: a private villa plus resort access and amenities. Part of Montego Bay’s Tryall Club, Sea Salt is a spacious five-bedroom property set on a golf course, known for its onsite chef that creates amazing Jamaican fare and more. Your included club membership allows you to join activities and events during your stay. View Sea Salt >

Amanyara 4-Bedroom Ocean Villa, Turks and Caicos

Luxury meets nature at Amanyara, the perfect spot to maximize your warm-weather outdoor time. Comprised of connecting pavilions, this villa is set on a nature reserve near a white sand beach. Use your included golf carts to get to the resort’s spa, restaurant, bar, fitness center, and volcanic rock infinity pool. View Amanyara 4-Bedroom Ocean Villa >

Tortuga Bay D1 at Punta Cana Resort, Dominican Republic

Trade skiing for snorkeling at this villa at the Punta Cana Resort, an exclusive Caribbean community. In addition to a variety of ocean adventures, you’ll enjoy a private pool (with shallow area for in-pool loungers), Jacuzzi, personal staff, outdoor dining area, and nearby beach. View Tortuga Bay D1 at Punta Cana Resort >

Browse all 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.