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

From USD p/night $ 12,150 /night

Fully Staffed

Upon Request

Fully Staffed

Serena Bonita

Caribbean, Las Terrenas, Playa Bonita

Adventure Vacations, Beachfront Villas, Caribbean Selection, Corporate Retreat, Food & Wine Collection, Large Retreats, Ocean View, Villas, Wedding Collection, Wellness Collection / Christmas & New Year Holidays 2025/2026, Fully Staffed Villas, Large Villas

From USD p/night $ 8,000 /night

Fully Staffed

From USD $ 8,450 /night

featured

Fully Staffed

5th Night Free

7th Night Free

From USD $ 20,000 /night

featured

Fully Staffed

ÀNI Anguilla | 10 BR

Anguilla Villas, Caribbean, The Valley

Adventure Vacations, Caribbean Selection, Large Retreats, Ocean View, Villas, Wellness Collection, Yoga Retreat / Event Villas, Breakfast Included, Christmas & New Year Holidays 2025/2026, Large Villas, Resort Facilities, Short Walk to the Beach

Upon Request

featured

Passage

Caribbean, St Barts Villas, Gustavia

Caribbean Selection, Honeymoon Collection, Ocean View, Summer 2026, Villas / Villa Near The Beach, Christmas & New Year Holidays 2025/2026

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 December 2025

Turks & Caicos (Providenciales)

Maskanoo (Boxing Day parade & street festival) — Fri, Dec 26, 2025 • Grace Bay. Junkanoo-style bands, food stalls, fireworks; roads close—book transfers.
Island Fish Fry (weekly) — Thursdays in December • The Bight/Grace Bay. Culture night with live rake-’n’-scrape and local vendors; arrive early for parking.

Barbados

Run Barbados Marathon & Wellness Weekend — Fri–Sun, Dec 5–7, 2025 • Bridgetown/St. Michael. Signature road races + wellness add-ons.
Carols by Candlelight (Rotary Barbados) — Sun, Dec 14, 2025 • Ilaro Court. Major charity concert; VIP sells out.
Christmas Morning in Queen’s Park — Thu, Dec 25, 2025 • Bridgetown. Fashion parade, bands, photos—go early.

St Martin / Sint Maarten

La Course de l’Alliance (tri-island regatta) — Sat–Mon, Dec 6–8, 2025 • Sint Maarten–St Barts–Anguilla. Season-opening sailing series.
Marigot Christmas Village & Grand-Case Lighting Parade — Late Dec windows (e.g., Sat, Dec 21 for Marigot village; check week-of).

St Barts

Gustavia Christmas Village — Mid-Dec (tourist board calendar). Artisanal stalls along the quay; family-friendly evenings.
New Year’s Eve in Gustavia — Wed, Dec 31, 2025. Harbor fireworks and super-yacht horn salute; book dinner and tenders early.

Punta Cana (DR)

NYE Headline Parties — Wed, Dec 31, 2025 • Punta Cana. Coco Bongo’s spectacle + beach-club galas (Pearl, resort galas); pre-book VIP.

Casa de Campo / La Romana (DR)

Altos de Chavón Christmas Tree Lighting — Sat, Dec 6, 2025 • 7:00 PM. Kick-off ceremony in the amphitheater village.
Holiday program & NYE celebrations — All December with concerts and beach fireworks; details roll out on the resort & community feeds.

Thanksgiving 2025: See our 5 villas approved for 5-night minimums in Turks & Caicos.

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

161 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

130 Listings

Discover

Chic Caribbean Hideaways

77 Listings

Caribbean Grandeur

801 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.