Caribbean Villa Rentals
Explore 1,300+ Caribbean villas for rent, from beachfront villa rentals to private estates with infinity pools, curated by Haute Retreats.
Trusted by discerning travelers worldwide | Luxury Lifestyle Awards Winner 2025
Featured
Caribbean Villa Rentals
15% Discount
20% Discount
Fully Staffed
Speak to a Caribbean Villa Specialist
Tell us your dates and must-haves, and we’ll send a curated shortlist of 3–5 villas—no fees, concierge included.
Caribbean Beach Villas
Fully Staffed
Special Offer
Caribbean Villas with Private Chef
Fully Staffed
Fully Staffed
Fully Staffed
Fully Staffed
Fully Staffed
Caribbean Villas available NYW 2026-2027
Fully Staffed
Fully Staffed
Fully Staffed
Events not to miss in February 2026
Holetown Festival — Sun–Sun, Feb 8–15, 2026 • Holetown (St. James), Barbados.
A week of Bajan heritage: craft fairs, cultural showcases, food stalls, and community celebrations marking Barbados’ first settlement—easy to pair with villa stays on the Platinum Coast.
Grenada Independence Day — Sat, Feb 7, 2026 • Island-wide (esp. St. George’s), Grenada.
National Day celebrations with ceremonies and cultural programming; expect crowds and occasional road closures near official events—flag early for transfers and dining reservations.
Reggae Month — Sun–Sat, Feb 1–28, 2026 • Jamaica (Kingston + island-wide).
A month-long celebration of reggae culture (tribute events, weekly programming, awards). Great timing for guests who want music, nightlife, and a deeper cultural layer beyond beach days.
Aruba Carnival Grand Parade Weekend — Thu–Mon, Feb 12–16, 2026 • San Nicolas & Oranjestad, Aruba.
Peak carnival days with the Lighting Parade (San Nicolas), Grand Parades (San Nicolas + Oranjestad), and the Burning of Momo—plan viewing spots and transport early.
Curaçao Carnival Peak Parades — Sun–Sun, Feb 1–15, 2026 (key parade dates) • Willemstad + Bandabou, Curaçao.
Highlights include the Horse Parade (Feb 1), Children’s Parade (Feb 8), Teen Parade (Feb 13), Bandabou Parade (Feb 14), and Gran Marcha (Feb 15). Book tables/bleachers where available.
Ponce Carnival (Carnaval Ponceño) — Thu–Tue, Feb 12–17, 2026 • Ponce, Puerto Rico.
One of Puerto Rico’s most iconic carnivals—mask culture, parades, music, and a high-energy street atmosphere. Ideal for guests who want a cultural “main event” trip.
Agrifest (USVI Agriculture & Food Fair) — Sat–Mon, Feb 14–16, 2026 • St. Croix, U.S. Virgin Islands.
A big local favorite: Crucian food, live entertainment, farmers market, crafts, and family-friendly activities—perfect daytime outing with a very “island life” feel.
Martinique Carnival — Sun–Wed, Feb 15–18, 2026 • Fort-de-France + island-wide, Martinique.
Four days of parades, costumes, and Mardi Gras traditions culminating around Ash Wednesday—expect the island to be in full celebration mode.
Guadeloupe Carnival “Jours Gras” — Sun–Wed, Feb 15–18, 2026 • Pointe-à-Pitre & Basse-Terre, Guadeloupe.
The climactic carnival stretch with major parades and “jours gras” festivities leading into Ash Wednesday—great for guests who want French-Caribbean culture at its most vibrant.
Trinidad & Tobago Carnival — Mon–Tue, Feb 16–17, 2026 • Port of Spain, Trinidad.
The Caribbean’s most famous carnival weekend (J’Ouvert + Pretty Mas). This is a “plan-your-whole-trip-around-it” event—accommodation, security, and transport should be arranged well in advance.
Saint Lucia Independence Day — Sun, Feb 22, 2026 • Island-wide (Castries + major towns), Saint Lucia.
Public holiday with cultural celebrations; useful to flag for itinerary planning because some services can run reduced hours and traffic may be heavier near official events.
Dominican Republic Independence Day — Fri, Feb 27, 2026 • Nationwide (Santo Domingo + resort areas), Dominican Republic.
National holiday with major celebrations and parades—excellent atmosphere for travelers, but plan logistics (bank/office closures and higher demand for drivers) accordingly.
Why Choose a
Caribbean Villa?
Choosing a luxury Caribbean villa means more than just a place to stay—it’s an experience. Unlike traditional resorts, our Caribbean villa rentals provide complete privacy, personalized service, and space for families, couples, or groups. Many of our Caribbean villas with staff include butlers, chefs, and daily housekeeping, ensuring every detail of your stay is effortless.
Exclusive collection of 1,300+ luxury villas in 25 destinations
Private pools, panoramic ocean views & full privacy
Villas tailored for families, couples, and large groups
Concierge service 24/7 to plan transfers, chefs, spa, and excursions
Professionally vetted luxury villa with verified photos and amenities
Luxury Villa Amenities
and Services
Every stay includes or can be arranged with:
Fully staffed villas with private chefs & housekeeping
Private pools, spacious sun decks & entertainment systems
Oceanfront & hillside estates with panoramic views
Family-friendly estates & large group accommodations
Concierge organizing transfers, yachts, wellness, golf & private tours
Best
Caribbean Destinations
Our portfolio spans the most exclusive islands in the Caribbean:
St. Barts luxury villas – jet-set glamour with breathtaking views.
Turks & Caicos villas – pristine beaches and chic design.
Barbados villa rentals – a blend of culture and luxury living.
Anguilla beachfront villas – tranquility and turquoise waters.
St Martin honeymoon villas – romance surrounded by lush landscapes.
Each island offers unique experiences, from sailing adventures to private chef dinners, ensuring your Caribbean villa rental is as memorable as the destination itself.
Island Elegance with French Flair
Secluded Shoreline Luxury
Chic Caribbean Hideaways
Caribbean Grandeur
Concierge and Experiences
Your villa, your private resort. We plan, book, and orchestrate—seamlessly.
How it works
Pre-arrival: itinerary, restaurant/beach-club holds, yacht/chef/spa, provisioning
Arrival: VIP greet, transfers or car to villa, chilled welcome
During stay: daily fine-tuning + on-call concierge
Signature experiences
Sea days (yacht, snorkel, sandbar) • Chef nights & tastings • Wellness (massage, yoga, PT) • Family care (sitters, kits, lessons) • Culture & adventure • Golf/tennis • After-dark moments
Island ideas
St Barts — Colombier yacht day • terrace tasting menu
Turks & Caicos — reef snorkel • kite on Long Bay
Anguilla — Sandy Island hop • live jazz night
Barbados — West Coast catamaran • rum heritage tasting
St Martin — Pinel/Tintamarre loop • French-side dining
Punta Cana — Corales golf • cenote & cigar experience
Good to know
Festive policies vary—book early • Vetted partners only • Transparent quotes • 24/7 support
Ready to plan?
Talk to a Caribbean Concierge • Reserve my Yacht Day • Curate my Chef Nights
Best Time to visit the Caribbean
December – April (Peak Season)
Enjoy flawless weather, calm turquoise seas, and a vibrant social scene. This is the season of exclusive yacht regattas, chic New Year’s Eve parties, and cultural festivals across the islands. (Ideal for travelers seeking glamour and perfect conditions.)
May – August (Shoulder Season)
Expect sunny days, warm evenings, and fewer crowds. Villas are more available, and rates are attractive — making it a great time for families and couples who want luxury without the peak-season bustle. Local food and music festivals bring extra color to the experience.
September – November (Low Season)
A tranquil time when nature flourishes, prices are at their most appealing, and the islands feel wonderfully private. While brief tropical rains are possible, this season is perfect for those seeking total seclusion and exceptional value.
What Our Guests Say
We stayed at an incredible villa in Ibiza booked through Haute Retreats — the experience was flawless, from the private chef to the sunset yacht charter. A dream vacation!
Lisa
USA
If you want the most amazing time, go with Haute Retreats! Sabrina is understanding, kind, patient and very true to her word! I will definitely book with Haute Retreats for my next adventure ☺️
Tricey
USA
Sabrina was amazing. It was my wife’s 40th birthday celebration. She found us the perfect villa in Turks and the staff was amazing. Best trip I have ever been on. Highly recommended!
Cristopher
USA
Frequently Asked Questions
When’s the best time to visit?
December–April is dry, buzzy, and peak. May–June and November are golden shoulder months with easier bookings and value. Late August–October is quiet and can be stormy—travel insurance and flexible plans are wise.
How do I get there and around?
Most guests route via hubs like Miami (MIA), San Juan (SJU), or St Maarten (SXM), then connect by regional flight or ferry. Small aircraft often have strict weight/size limits—soft-sided bags help. On-island, a compact SUV offers freedom; in smaller islands, drivers and boat transfers can replace long road time.
Which island fits my style?
For scene and dining: St Barts, Barbados.
For barefoot-chic beaches and privacy: Turks & Caicos, Anguilla.
For wellness and scenery: St Lucia.
For sailing/yachting vibes: Antigua, BVI.
Share your dates and vibe (party, wellness, family, foodie) and we’ll match the right island + villa.
What comes with a luxury villa (vs. a resort)?
Privacy and space plus hotel-level services: housekeeping, concierge, pre-arrival provisioning, in-villa chef nights, spa/wellness, yacht days, childcare. Minimum stays and Festive policies vary; we secure restaurant/beach-club holds and activity slots before you land.
Money, tipping, power & connectivity—anything tricky?
Currencies vary (USD in Bahamas/USVI, EUR in French islands, XCD elsewhere), but cards are widely accepted. Many restaurants add a service charge; if not, 10–15% is customary. Power is mostly 110V US-style, except French islands (230V Type-E)—pack an adapter. eSIMs and villa Wi-Fi make staying connected easy.
Book Your Caribbean Villa with Haute Retreats
Over 1,300 luxury villas & resorts across 25 Caribbean islands. Tailored stays, private pools, and full concierge service for your dream escape.
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