How do I get there and get around?

Most travelers route via hubs like Miami (MIA), San Juan (SJU), or St Maarten (SXM) and connect by regional flight or ferry. Small planes often have strict baggage limits—soft-sided bags help. On-island, a compact SUV provides freedom; on smaller islands, private drivers and boat transfers work well.

What comes with a luxury villa versus a resort?

Villas offer privacy and space with hotel-level services: housekeeping, concierge, pre-arrival provisioning, in-villa chef nights, spa/wellness, yacht days, and childcare. Minimum stays and Festive policies vary; top restaurants and beach clubs should be reserved ahead.

Caribbean Villas

+1,300 luxury Caribbean villas & luxury resorts across 25 islands—private pools, fully staffed options, and concierge from planning to departure.

Discover the finest Caribbean Villas, where turquoise waters, white-sand beaches, and unmatched privacy create the ultimate luxury escape. Haute Retreats offers over 1,300 handpicked Caribbean villas for rent, each curated for exclusivity, comfort, and world-class amenities. From private Caribbean villas with infinity pools to beachfront Caribbean vacation rentals with direct ocean access, your dream getaway starts here.

Trusted by discerning travelers worldwide | Luxury Lifestyle Awards Winner 2025

Featured

Caribbean Villa Rentals

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.

Events not to miss in January 2026

Turks & Caicos (Providenciales)
Island Fish Fry (weekly culture + street food night) — Thu evenings in January 2026 (e.g., Jan 15, 22, 29) • The Bight / Grace Bay. Open-air food, live rake-’n’-scrape, Junkanoo; arrive early or use a driver as parking is limited.

Barbados
Flower & Garden Festival — Fri–Mon, Jan 16–19, 2026 • St Peter’s Parish Church, St Peter. Floral displays, garden tours and teas on the north coast; good to pair with a Speightstown lunch.

Under the Sun Art Festival — Sat, Jan 17, 2026 • Haymans Market, St Peter. Open-air art market with local creatives, food stalls and live entertainment; go earlier in the day for a quieter feel

St Martin / Sint Maarten
St Maarten Carnival Warm-Up (parade rehearsals & band tryouts) — From Sun, Jan 11, 2026 • Various locations, Dutch side. Early-season rehearsals, band practices and small fetes leading into Carnival; check the week-of schedule for specific nights.

Caribbean Multihull Challenge VIII — Thu–Sun, Jan 29–Feb 1, 2026 • Simpson Bay / around Sint Maarten. High-performance catamaran and trimaran regatta with great yacht-spotting from shore and beach bars.

St Barts
St Barth Music Festival — Fri–Mon, Jan 9–19, 2026 • Island-wide (Gustavia, Lorient, churches). Classical music, opera, jazz and dance performances with international artists; tickets and restaurant reservations should be booked well in advance

Punta Cana (DR)
SweatFest Punta Cana — Thu–Mon, Jan 15–19, 2026 • Hard Rock Hotel & Casino Punta Cana. Five-day R&B and comedy festival with headline acts and resort-only programming; typically sold as an all-inclusive package with minimum-night stays.

Casa de Campo / La Romana (DR)
Morrissey – The Hits Tour — Sun, Jan 25, 2026 • Altos de Chavón Amphitheater, Casa de Campo. One-night concert in the open-air stone amphitheater; gates usually open early evening, so plan transfers from Punta Cana or on-property villas accordingly.

The Best Place to Celebrate New Years in 2025/26: Caribbean Villas by Haute Retreats

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.

St Martin Villas

160 Listings

Discover

Island Elegance with French Flair

Grace Bay

62 Listings

Discover

Turquoise Dream Escapes

Anguilla Villas

56 Listings

Discover

Secluded Shoreline Luxury

St Barts Villas

132 Listings

Discover

Chic Caribbean Hideaways

79 Listings

Caribbean Grandeur

806 Listings

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.