Caribbean Vacation Rentals

Luxury Villa Rentals in Caribbean for 2+ people

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$425 - $700 /night

Seas the Paradise

2 Bedroom Penthouse, 3 Bathrooms, Sleeps 4
Seas the Paradise at Las Arenas is a luxury top floor penthouse two bedroom two and a half bathroom condo located on St. Maarten’s longest beach – the Simpson Bay Beach. This 4th-floor apartment offers fantastic ocea... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
$425 - $700 /night

Waterside 303

2 Bedroom Apartment, 2 Bathrooms, Sleeps 4
Apartment 303, situated on the second floor, is a spacious 2-bedroom apartment that has been nicely furnished and finished to an exceptional standard. Both bedrooms have ensuite bathrooms and personal closet space. The o... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
$425 - $895 /night

Cayman Dream

2 Bedroom Villa, 2 Bathrooms, Sleeps 6
Cayman Dream sits directly oceanfront in Rum Point along the north coast. Featuring Caribbean-style architecture and a sizable oceanfront pool, Cayman Dream is a great getaway for small families or a pair of vacationing ... more
Additional Fees: Departure Cleaning Fee $125.00 flat, Damage Waiver $299.00 flat
Taxes: 28%
$420 - $850 /night

Beacon Hill 305 | Penthouse

3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Enjoying one-of-a-kind views of the Caribbean Sea while unwinding in a private plunge pool on your rooftop terrace. This West Coast Barbados penthouse has it all and is located across from Mullins Beach in the exclusive ... more
Additional Fees: Damage Waiver $299.00 flat, Cleaning Fee $150.00 flat
Taxes: 12.5%
$414 - $1,171 /night

Cheyenne

3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The vacation rental Cheyenne is a charming property located in Vitet overlooking the ocean and the lagoon of Grand-Cul-de-Sac. Very well equipped and located close to all amenities, this three-bedroom villa with a swimmi... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
$414 - $1,714 /night

Kyody

2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Built on a hillside on the heights of Marigot, the charming villa Kyody in St-Barths overlooks the beautiful lagoon of Grand-Cul-de-Sac and offers a spectacular panoramic view over the bay and the surrounding hills. T... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
$407 - $983 /night

Greystone

3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Nestled in the highly sought-after Terres Basses area, Villa Greystone boasts a prime location on the island. This upscale residential neighborhood is known for its tranquility, security, and proximity to the most stunni... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
$400 - $1,150 /night

Parnassus Cottage

2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Guests staying within the world-famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts. Discover luxury living at its... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
$400 - $1,171 /night

La Dorade

2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Located on the heights of Colombier, La Dorade is a charming Caribbean-style villa with a panoramic view over the ocean and the glorious sunsets. Very well equipped and close to all amenities, this two-bedroom vacation r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
$398 - $6,143 /night

Anticipation

6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
$395 - $775 /night

KiToCay

3 Bedroom Villa, 2 Bathrooms, Sleeps 6
Welcome to KiToCay! This 3,000 sq. ft. home is located in the village of Old Man Bay on the island's beautiful North Side. KiToCay boasts a panoramic oceanfront living area with spectacular views, plus an over-the-wa... more
Additional Fees: Departure Cleaning Fee $295.00 flat, Damage Waiver $299.00 flat
Taxes: 28%
$350 - $1,500 /night

Forest Hills 35 | Bajan Sunset

2 Bedroom Apartment, 2 Bathrooms, Sleeps 4
Forest Hills 35 is a private end-of-row, two-bedroom villa, which benefits from Westerly sea views - this well-maintained golf residence is permanently staffed by an attentive housekeeper who will look after all your nee... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
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