Caribbean has 180 vacation rentals, with the most in Noord, Saint-François, and Cruz Bay. They host 22 to 30 guests and sleep 8 to 50 overnight. Common features include amazing views, outdoor pool, and beach. 141 have guest reviews, averaging 4.9 out of 5.
Best Vacation Rentalsin Caribbean
Showing 10 of 180 venues
Santosha Villa Estate, Private Staffed Beach Resort All to Yourself, Sleeps 21
Santosha Villa Estate, Private Staffed Beach Resort All to Yourself, Sleeps 21 Enter Caribbean bliss at our ultra-private, beachfront enclave, Santosha Villa Estate on secluded Long Bay Beach. Santosha is more than a villa, it’s an experience. It’s a 5-star private beachfront res…
Nevaeh Villa Exclusive 9 bedroom fully staffed beachfront estate
Nevaeh Villa - Exclusive 5-9 bedroom fully staffed beachfront estate. Exclusive, Balinese-inspired, beachfront estate with direct access to a half mile of pristine white sand beach on Long Bay. Just minutes from the popular west end of Anguilla, Nevaeh is heaven spelled backwards…
Sandcastle Villa & Beach House - ON THE BEACH Luxury Villa & Beach House, Sleeps 20, Pools, Hot-tubs, Fire-pits…
4.9ON THE BEACH Luxury Villa & Beach House, Sleeps 20, Pools, Hot-tubs, Fire-pits… 🏝️ Sandcastle Estate – The Ultimate Dual-Villa Experience Sandcastle Villa + Sandcastle Beach House | Limestone Bay, Anguilla Indulge in the epitome of Caribbean luxury by renting Sandca…
Memories in Cultural Luxury???? Estate in the Caribbean Culinary Capital w/staff
Memories in Cultural Luxury😌- Estate in the Caribbean Culinary Capital w/staff Perched atop the highest point of Travel + Leisure’s four-years-in-a-row #1 Caribbean Island, ViewFort Estate, invites you to immerse in Pure Anguilla while enjoying peace of mind, so you can focus on…
Villa Indigo by Fantasia Villas
Villa Indigo by Fantasia Villas Let the lush gardens, white sands and turquoise waters of the Caribbean be the backdrop to a family getaway or special occasion at Indigo. Set in the lee of Cinnamon Reef on Little Harbor, the villa is tucked into 1.5 acres and has its own beach. W…
Sea Villa at Long Bay Villas: Privacy, 5star service, butler, on secluded beach
4.9Hello, we are the owners of ultra-luxury 5/6-bedroom Sea Villa at Long Bay Villas Anguilla on secluded Long Bay Beach. Long Bay Villas is featured on Netflixs The Worlds Most Amazing Vacation Rentals Season 2 and is Anguillas largest and most private staffed, luxury property with…
Blue Diamond Private Villa at Altamer
Blue Diamond - Private Villa at Altamer This 13,000 sq. ft. villa with new renovations that were finished in November 2021. Blue Diamond’s unique flower-shaped design is perfect for large groups and all three levels have a central common area surrounded by smaller, individual roo…
Villa Anguillitta Entire 7BD Villa w/ Private Beach Access, Sauna, Gym, & Pool
Villa Anguillitta: Book Fall & Holiday Now And Get 10% Off! Welcome to Villa Anguillitta – Your Private Caribbean Oasis Perched above the turquoise waters of Anguilla’s scenic south coast, Villa Anguillitta is a private 7-bedroom, 8.5-bathroom villa made up of five unique suites—…
Stunning 6 bedroom waterfront villa with wooden dock
4.9Angel Point villa is a contemporary 6-bedroom villa set on the point of a calm harbor in Anguilla. Completely restructured and renovated in 2023, Anguilla’s newest waterfront villa has become the perfect Caribbean getaway with stunning views over St Martin from every room on prop…
VILLA ALEGRIA: BEST VIEWS IN ANGUILLA & 60 SECONDS TO BEACH + POOL, JACUZZI, GYM
4.8VILLA ALEGRIA: BEST VIEWS IN ANGUILLA & 60 SECONDS TO BEACH + POOL, JACUZZI, GYM Villa Alegria Anguilla is a private luxury villa near Blowing Point on Anguilla's desirable West End. Alegria is one of the Caribbean's most beautiful and comfortable oceanfront villas with stunning…
Santosha Villa Estate, Private Staffed Beach Resort All to Yourself, Sleeps 21
Anguilla
Santosha Villa Estate, Private Staffed Beach Resort All to Yourself, Sleeps 21 Enter Caribbean bliss at our ultra-private, beachfront enclave, Santosha Villa Estate on secluded Long Bay Beach. Santosha is more than a villa, it’s an experience. It’s a 5-star private beachfront res…
Nevaeh Villa Exclusive 9 bedroom fully staffed beachfront estate
Anguilla
Nevaeh Villa - Exclusive 5-9 bedroom fully staffed beachfront estate. Exclusive, Balinese-inspired, beachfront estate with direct access to a half mile of pristine white sand beach on Long Bay. Just minutes from the popular west end of Anguilla, Nevaeh is heaven spelled backwards…
Sandcastle Villa & Beach House - ON THE BEACH Luxury Villa & Beach House, Sleeps 20, Pools, Hot-tubs, Fire-pits…
4.9Anguilla
ON THE BEACH Luxury Villa & Beach House, Sleeps 20, Pools, Hot-tubs, Fire-pits… 🏝️ Sandcastle Estate – The Ultimate Dual-Villa Experience Sandcastle Villa + Sandcastle Beach House | Limestone Bay, Anguilla Indulge in the epitome of Caribbean luxury by renting Sandca…
Memories in Cultural Luxury???? Estate in the Caribbean Culinary Capital w/staff
Anguilla
Memories in Cultural Luxury😌- Estate in the Caribbean Culinary Capital w/staff Perched atop the highest point of Travel + Leisure’s four-years-in-a-row #1 Caribbean Island, ViewFort Estate, invites you to immerse in Pure Anguilla while enjoying peace of mind, so you can focus on…
Villa Indigo by Fantasia Villas
Anguilla
Villa Indigo by Fantasia Villas Let the lush gardens, white sands and turquoise waters of the Caribbean be the backdrop to a family getaway or special occasion at Indigo. Set in the lee of Cinnamon Reef on Little Harbor, the villa is tucked into 1.5 acres and has its own beach. W…
Sea Villa at Long Bay Villas: Privacy, 5star service, butler, on secluded beach
4.9Anguilla
Hello, we are the owners of ultra-luxury 5/6-bedroom Sea Villa at Long Bay Villas Anguilla on secluded Long Bay Beach. Long Bay Villas is featured on Netflixs The Worlds Most Amazing Vacation Rentals Season 2 and is Anguillas largest and most private staffed, luxury property with…
Blue Diamond Private Villa at Altamer
Anguilla
Blue Diamond - Private Villa at Altamer This 13,000 sq. ft. villa with new renovations that were finished in November 2021. Blue Diamond’s unique flower-shaped design is perfect for large groups and all three levels have a central common area surrounded by smaller, individual roo…
Villa Anguillitta Entire 7BD Villa w/ Private Beach Access, Sauna, Gym, & Pool
Anguilla
Villa Anguillitta: Book Fall & Holiday Now And Get 10% Off! Welcome to Villa Anguillitta – Your Private Caribbean Oasis Perched above the turquoise waters of Anguilla’s scenic south coast, Villa Anguillitta is a private 7-bedroom, 8.5-bathroom villa made up of five unique suites—…
Stunning 6 bedroom waterfront villa with wooden dock
4.9Anguilla
Angel Point villa is a contemporary 6-bedroom villa set on the point of a calm harbor in Anguilla. Completely restructured and renovated in 2023, Anguilla’s newest waterfront villa has become the perfect Caribbean getaway with stunning views over St Martin from every room on prop…
VILLA ALEGRIA: BEST VIEWS IN ANGUILLA & 60 SECONDS TO BEACH + POOL, JACUZZI, GYM
4.8Anguilla
VILLA ALEGRIA: BEST VIEWS IN ANGUILLA & 60 SECONDS TO BEACH + POOL, JACUZZI, GYM Villa Alegria Anguilla is a private luxury villa near Blowing Point on Anguilla's desirable West End. Alegria is one of the Caribbean's most beautiful and comfortable oceanfront villas with stunning…
Frequently Asked Questions
How many vacation rentals are in Caribbean?
There are 180 vacation rentals listed in Caribbean, spread across 107 cities and towns.
Which cities in Caribbean have the most vacation rentals?
Noord leads with 7, followed by Saint-François (6) and Cruz Bay (5).
How many guests can Caribbean vacation rentals host?
Guest capacity ranges from 22 to 30 across the 4 listings that state it.
How many people do Caribbean vacation rentals sleep?
180 rentals list their sleeping capacity, from 8 to 50 people.
How are Caribbean vacation rentals rated?
141 of 180 listings have guest reviews, with an average rating of 4.9 out of 5.
What amenities are most common at Caribbean vacation rentals?
Amazing Views is the most common (175 listings), followed by outdoor pool (173) and beach (164).
How do I book a vacation rental in Caribbean?
Browse the 180 Caribbean vacation rentals here, compare capacity, photos, and amenities, then contact the host directly to check availability for your date.