Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$929 - $3,429 /night
Ker Anna
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
With a wonderful panoramic view over St Jean Bay, Villa Ker Anna is a colour-filled dream both inside and out. The blue Atlantic Ocean stretches off toward Sint Maarten on the horizon, the green leaves of palm and guaiac sway in the breeze, and the interi... more
$929 - $3,000 /night
Étoile de Mer
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Villa Étoile de Mer – Refined Oceanfront Living at Shore Pointe
Set directly at the water’s edge within the exclusive, gated enclave of Shore Pointe, Villa Étoile de Mer is a rare oceanfront residence offering an exceptional balance of privacy, s... more
$929 - $4,229 /night
Wheel House
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$929 - $3,571 /night
Matajagui
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Built on the hills of Flamands, the sumptuous rental villa Matajagui offers a high range of services in a refined and modern atmosphere. Located only a few steps away from the Flamands beach, this charming property is built over two storeys and has an ope... more
$925 - $3,050 /night
Harmony House
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Nearby construction may result in noise disturbances. For further details on how this might affect your stay, please reach out to a Rental Escapes villa specialist.
Please note the beach experiences seasonal fluctuations in its... more
$920 - $3,740 /night
Villa Nirvana
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Step into a true haven of peace at Villa Nirvana, recently renovated and nestled in the heart of Terres Basses. This stunning six-bedroom villa perfectly blends Caribbean elegance, modern comfort, and a relaxed beach atmosphere, promising unforgettable va... more
$920 - $1,765 /night
Monte Verde
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Villa Monte Verde – a lavish four-bedroom villa in Orient Bay in St Martin, where breathtaking ocean views and unparalleled serenity beckon.
Nestled high above Orient Bay in Saint-Martin, Villa Monte Verde is a symbol of luxury and tranquility. This ... more
$914 - $1,571 /night
Villa Francais
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
In late 2022, this spacious villa was completely repainted, the pool deck was replaced, and all new furnishings were added throughout!
This magnificent Spanish-style family villa boasts five bedrooms, each with its own ensuite bathroom, a guest bathroo... more
$900 - $1,500 /night
Villa L'Optimiste
4 Bedroom Apartment, 4 Bathrooms, Sleeps 12
Four bedroom luxury villa rental. Introducing the epitome of luxury coastal living, nestled within the prestigious gated beachfront resort of Sea Horse Ranch. Villa l’Optimiste is a two-story, expansive residence with four bedrooms, four bathrooms, a sw... more
$900 - $1,500 /night
Villa Diana
4 Bedroom Apartment, 5 Bathrooms, Sleeps 8
Villa Diana is a luxury vacation villa with exquisite space and location. This four bedroom luxury Caribbean property is a classic beach villa with beautiful architecture, an open floor plan, and harmonious interiors embodying both sophistication and rela... more
$900 - $3,900 /night
Songbird Villa
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Songbird Villa is a captivating five-bedroom retreat designed to offer a truly remarkable Caribbean experience. Situated in the middle of the finest luxury villas in Anguilla, Songbird Villa masterfully blends modern style living with the traditional ease... more
$900 - $2,524 /night
The Bay Suites
1 Bedroom Apartment, 1 Bathrooms, Sleeps 2
The Bay Suites offer a luxurious, comfortable retreat with beautiful views of the Caribbean Sea and the lush surrounding area. Tucked into the hillside beyond Oil Nut Bay’s Beach Club, each suite offers a master bedroom with ensuite spa bathroom and pri... more