Caribbean Vacation Rentals

Luxury Villa Rentals in Caribbean for 2+ people

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$10,183 - $19,167 /night

Osprey

4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Osprey is a four-bedroom oceanfront villa, perfect for families or groups seeking a tranquil getaway. Nestled beside Aurora Villa, it offers an ideal setup for larger parties needing eight bedrooms while enjoying the pri... more
Additional Fees: Damage Waiver $299.00 flat
$10,183 - $17,969 /night

Land's End

4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Land's End is an ideal villa for those seeking maximum privacy. Located on Whale Watchers Point, where the Atlantic Ocean meets the Caribbean Sea, this light-house-inspired villa is arguably the most unique home on the i... more
Additional Fees: Damage Waiver $299.00 flat
$10,183 - $17,969 /night

Carpe Diem

4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Carpe Diem is a modern 4-bedroom villa offering breathtaking views of the Iron Shore coastline and bay, along with 360-degree views from a rooftop deck—perfect for enjoying a sunrise coffee or sunset cocktails with fri... more
Additional Fees: Damage Waiver $299.00 flat
$10,120 - $26,160 /night

Le Bleu Villa

11 Bedroom Villa, 12 Bathrooms, Sleeps 22
Le Bleu is a stunning beachfront Anguilla villa rental with modern Caribbean luxury. Nestled within 2.5 acres of private grounds, this extraordinary Anguilla real estate property offers breathtaking views of Cinnamon Ree... more
Additional Fees: Damage Waiver $299.00 flat, Security Deposit $5000.00 flat
Taxes: 23%
$10,000 - $32,000 /night

Footprints

8 Bedroom Villa, 8 Bathrooms, Sleeps 16
Designed around a palm- and pond-filled courtyard, offering ocean views from every bedroom, this property is the epitome of understated glamour. With a prime beachfront position, an abundance of space indoors and out, an... more
Additional Fees: Damage Waiver $299.00 flat, Security Deposit $10000.00 flat
Taxes: 22%
$10,000 - $39,270 /night

Salacia

9 Bedroom Villa, 10 Bathrooms, Sleeps 18
Villa Salacia is a spectacular beachside estate nestled within 1.5 acres of lush tropical gardens, bursting with vibrant colour and fragrance. Soft, powdery sands and crystalline turquoise waters are visible at every tu... more
Additional Fees: Damage Waiver $299.00 flat, Security Deposit $5000.00 flat
Taxes: 22%
$10,000 - $28,571 /night

Dei Sogni

6 Bedroom Villa, 6 Bathrooms, Sleeps 12
In Italian, the name Dei Sogni means “of dreams.” Which makes it a very fitting name for the new Villa Dei Sogni, right on Lorient Beach. This luxury rental property is one of a kind on St. Barth. It gives guests an ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
$9,950 - $23,950 /night

Castillo Caribe

7 Bedroom Villa, 14 Bathrooms, Sleeps 14
Castillo Caribe is undoubtedly one of the finest beachfront estates in the world, offering a luxury lifestyle in an exceptionally lavish oceanfront estate. Commanding far-reaching views of the Caribbean sea with a str... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 34.4%
$9,950 - $20,500 /night

6 BDM Private Villa at The Shore Club

6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Exquisite, hand-crafted tiles and bespoke elements grace this sophisticated Villa. Only steps away lays a magnificent 800-foot stretch of white sand and the aquamarine waters of the secluded Long Bay Beach. All of th... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 25%
$9,800 - $34,500 /night

Casa Caleton

12 Bedroom Apartment, 12 Bathrooms, Sleeps 24
All guests must register with the Casa de Campo Concierge office, and for a small daily fee ($30 per adult per night & $15 per child per night), are granted access to resort areas and amenities. Casa de Campo Res... more
Additional Fees: Damage Waiver $299.00 flat, Food & Beverage Deposit $2000.00 flat
Taxes: 18%
$9,750 - $26,500 /night

Emerald Breeze

6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Moments from Grace Bay and the Blue Haven marina on the eastern tip of Providenciales, Emerald Breeze is a new-to-market six-bedroom villa with its own private guesthouse. Stretching over two stunning floors, this discre... more
Additional Fees: Security Deposit $5000.00 flat, Damage Waiver $299.00 flat
Taxes: 22%
$9,625 - $12,375 /night

Villa Kayanta

6 Bedroom Villa, 7 Bathrooms, Sleeps 14
Guests staying within Cap Cana will have access to all resort amenities and facilities. Resort amenities and facilities include a golf course ($), spa ($), restaurants ($), bars ($), fitness centre ($) and tennis... more
Additional Fees: Security Deposit $9750.00 flat
Taxes: 6%
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