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Sun-Soaked Escapes: 9 Luxurious Villas for a Warm Caribbean Winter

Category: Insiders Guide | 09.28.2023

As winter’s chill will soon descend upon much of the world, there’s a timeless allure to seeking refuge in the Caribbean—a haven where the sun reigns supreme, warm breezes caress your skin, and the rhythm of island life invites you to unwind and indulge. If you’re dreaming of an escape that transcends the ordinary, we have a curated selection of Caribbean villas that embody the essence of luxury, tranquility, and endless sunshine.

Our journey takes us to nine distinct Caribbean destinations, each offering its own unique charm and character. From the pristine shores of Anguilla to the vibrant culture of Jamaica, these luxurious villas promise an unforgettable winter retreat. Whether you’re seeking a romantic getaway for two, a family adventure in paradise, or a grand gathering of friends, there’s a villa here to make your Caribbean dreams come true.

Join us as we embark on a sun-soaked escapade, exploring the exquisite beauty of the Caribbean and the lavish comfort of these handpicked villas. Warmth, relaxation, and pure indulgence await in the heart of the tropics, where winter is just another glorious day in paradise.

Let’s discover the magic that awaits at each of these nine luxurious villas, beckoning you to trade your winter blues for sun-soaked hues. 🌞🏝️

#1 Long Bay Villa Santosha in Anguilla

9 Beds/ 9 Baths/ Capacity: 18

From the private pool to the beach access, Santosha has everything you’ll need for that large group. Boasting 9 bedrooms and accommodating up to 18 guests this villa is perfect for those who wish to lounge away the days in the sunshine and entertain at night. A barbecue and full amenities round out the potential of this spacious home.

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#2 Morning Glory Estate in Antigua

8 Beds / 9.5 Baths/ Capacity: 16

This fabulous, colonial-style villa is set on 8 private acres of lush gardens. Offering 4 bedroom suites in the main house and 2 private cottages, each featuring 2 suites, this gorgeous home opens directly onto a show-stopping white sand beach and exceptional ocean views. Enjoy the 20 meter long infinity pool, the modern kitchen with breakfast terrace, 2 dining areas in the main house and a dining gazebo adjacent to the beach, when a meal set to the soundtrack of waves lapping against the shore are in order. In all, this is the perfect private retreat for families or larger groups.

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#3 Martello House in Barbados

8 Beds / 8.5 Baths/ Capacity: 16

Located on Barbados’ west coast, overlooking the Royal Westmorland Golf Course and a clear view all the way to the Caribbean Sea, Martello House is the very epitome of tropical luxury and serenity. Completely private, this 8 bedroom villa also offers all the amenities of a resort. There’s the infinity pool with its uninterrupted views, a plunge pool, and lush gardens all around, along with a media room and modern kitchen.

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#4 Villa Lucia in Dominican Republic

6 Beds/ 6 Baths/ Capacity: 16

Large and luxurious is the way of life here at Villa Lucia. Offering 6 bedrooms, two floors of comfortable and well-appointed living space, a large pool, and many great amenities, all surrounded by a mature garden, this villa is the perfect choice for a Caribbean escape. While some of the bedrooms enjoy private terraces, all are very roomy and each have their own en-suite baths. The large pool and surrounding wooden deck are perfect for long, sun-drenched days with a good book or refreshing cocktail in hand, and inside, the media room, formal dining room and modern kitchen await.

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#5 Point of View Villa in Grand Cayman

6 Beds/ 6 Baths/ Capacity: 16

Located on Grand Cayman’s stunning South Sound, this remarkable 6-bedroom villa offers a host of luxuries that are both simple and sublime. Inside, the home features every imaginable amenity- a fully outfitted chef’s kitchen, a media room with a 70′ flat screen TV, 2 oceanfront master suites, a bunk room for the kids and so much more. Outside, there’s the pool and the beach, along with a sumptuous outdoor living space complete with a fire feature, 2 hot tubs, a kids pool, an outdoor kitchen, and a private dock with a shaded gazebo. A kayak and paddleboard are also provided.

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#6 Ma’Moura in Jamaica

4 Beds/ 4 Baths/ Capacity: 8

The ultimate in unobstructed views, Ma Moura is centered around the luxurious circular pool and spacious verandah. Guests tend to gather here to take in the views of the sea beyond the golf course. Vistas are on offer from every room and the sliding glass doors let in the tropical ocean breezes. Combine all this with an uncompromising staff and Ma Moura is the perfect vacation getaway.

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#7 Sous la Falaise in St Barth’s

4 Beds/ 4 baths/ Capacity: 8

Nestled just above the water at the eastern end of St. Jean Beach, this 4-bedroom villa is both private and conveniently located, within easy walking distance along the beach to St. Jean’s shops and restaurants. Spread out over multiple buildings – with one main bungalow housing the kitchen, living and dining areas, and individual bedroom cottages – this home is great for those looking for quality time together while also enjoying amply private time. There’s a large pool, along with a barbecue area.

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#8 Beach Kandi in Turks and Caicos

2 Beds / 2 Baths/ Capacity: 4 

This modern, 2-bedroom beachfront villa in Turtle Cove boasts spectacular views of the region’s clear, turquoise waters. Spread out over 1,800 sq.ft., there’s a fold-away glass wall that turns the open-plan great room into a breezy indoor-outdoor living space with the beach just a few steps away. Recline on the sitting area’s sofas and watch the waves lap the shore, or check out your favourite show on the pop-up television.

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#9 Villa Arc en Ciel in Saint Lucia

5 Beds/ 5 Baths/ Capacity: 10

Spectacularly situated on Beau Estate, between the stunning Pitons and the turquoise waters of the Caribbean Sea, this 5-bedroom private villa offers the very highest standard of island life. Just a short distance from Sugar Beach and close to the town of Soufriere, this home incorporates many aspects of traditional Caribbean style with its verandahs, jalousie shutters and wooden accents. It also boasts a private infinity pool and sun deck, an enclosed garden area, a casual and comfortable living/dining space, along with a formal dining area and modern kitchen.

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