Where to Stay for Thanksgiving: Caribbean Villas Crafted for Celebration & Serenity

This Thanksgiving, trade traditional tablescapes for turquoise waters, and the stress of hosting for the serenity of sun-soaked private retreats. Whether you’re craving intimate family time, barefoot luxury, or the simple pleasure of waking up to waves instead of alarms, Haute Retreats delivers an unforgettable holiday escape.

As the winner of the Luxury Lifestyle Awards 2025 for Best Luxury Villa Rentals Company in the World, Haute Retreats curates only the most exquisite Caribbean villas for rent—perfectly suited for luxurious celebration and restorative serenity.

Here are seven spectacular Caribbean villas for rent to consider for your Thanksgiving retreat, including top-tier St Barts villas and exquisite properties in Turks & Caicos, Punta Cana, and Anguilla.

Villa Emerald Pavilion – Turks and Caicos

Located on the pristine Leeward Beach,  Villa Emerald Pavilion offers beachfront access, five-star amenities, a heated pool, butler and chef services, and an oceanfront firepit ideal for sunset gatherings. It’s Thanksgiving reimagined—Caribbean style.

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Villa Dune House – Turks and Caicos

This 8-bedroom ultra-modern retreat boasts a private tennis court, two infinity pools, panoramic views, and over 10,000 sq. ft. of indoor-outdoor luxury. Perfect for multi-generational families craving both connection and privacy.

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Villa Milestone – Turks and Caicos

Just steps from Grace Bay, this 8-bedroom gem blends modern elegance with barefoot beach charm. Think outdoor movie nights, alfresco dining, and full staff service that turns every day into a celebration.

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Villa Ana – Flamands, St Barts

Perched above Flamands Beach, this sleek, sun-drenched villa features a private infinity pool and panoramic ocean views. Ideal for a chic, intimate Thanksgiving celebration in true French-Caribbean flair.

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Villa 3H – St Barts

A beautifully balanced mix of island minimalism and modern luxury. With three bedrooms, it’s perfect for smaller groups looking for sophistication, seclusion, and sea views.

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Villa Nevaeh – Anguilla

Meaning ‘heaven’ spelled backwards, Villa Nevaeh lives up to its name with 1.35 acres of  beachfront opulence. Highlights include a golf simulator, theater room, tennis court, and personal chef—Thanksgiving has never been this elevated.

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Villa Ananda – Punta Cana

One of the most elegant Punta Cana villas for rent, this 8-bedroom estate offers oceanfront serenity, golf course access, a private pool, jacuzzi, and daily chef services. Celebrate gratitude with Caribbean elegance and Dominican warmth.

Whether you’re escaping the cold or simply redefining tradition, these Haute Retreats Caribbean villas for rent provide the ideal setting for a luxurious, gratitude-filled Thanksgiving. With stunning views, curated experiences, and white-glove service, every moment becomes a memory.

Let Haute Retreats transform your holiday into a once-in-a-lifetime celebration in paradise—whether you choose a Punta Cana villa, a beachfront retreat in Turks & Caicos, or an elegant escape in St. Barts or Anguilla.