Luxury Vacations in the Caribbean

Caribbean
Anytime
2 guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Luxury Vacations in the Caribbean

Luxury vacations in the Caribbean are extremely popular with tourists looking for a little tropical paradise. From pearly white beaches dotted with swaying palm trees, to windswept coves and blissful surfing reefs, the Caribbean has plenty of hidden gems.

Luxury Holidays in the Caribbean: Top Accommodations

House Saint-Francois
House ∙ 6 guests ∙ 3 bedrooms
Saint-Francois, Grande-Terre, Guadeloupe
from $319
Muchosol
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Villa Providenciales
Villa ∙ 6 guests ∙ 3 bedrooms
Providenciales, Turks and Caicos Islands
from $863
Casamundo
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Villa Collectivity of Saint Martin
Villa ∙ 6 guests ∙ 3 bedrooms
Collectivity of Saint Martin, Saint Martin
from $412
Dream Villas
5.0/5.0
"Excellent"
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Villa Anguilla
Villa ∙ 4 guests ∙ 2 bedrooms
Anguilla
from $946
Onefinestay
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Villa Collectivity of Saint Martin
Villa ∙ 6 guests ∙ 3 bedrooms
Collectivity of Saint Martin, Saint Martin
from $769
Dream Villas
5.0/5.0
"Excellent"
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House Grenadines
House ∙ 6 guests ∙ 3 bedrooms
Grenadines, Saint Vincent and the Grenadines
from $171
Vrbo
5.0/5.0
"Excellent"
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House St. Thomas
House ∙ 6 guests ∙ 3 bedrooms
St. Thomas, U.S. Virgin Islands
from $188
Vrbo
4.9/5.0
"Excellent"
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House Richmond
House ∙ 5 guests ∙ 2 bedrooms
Richmond, Grenadines, Saint Vincent and the Grenadines
from $120
Vrbo
5.0/5.0
"Excellent"
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House Hastings
House ∙ 6 guests ∙ 3 bedrooms
Hastings, Bridgetown, Barbados
from $52
Vrbo
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The Best Caribbean Islands for Luxury Vacations

Discover serenity, pure bliss and sheer fun in the Caribbean Islands that will keep you coming back for more. Whether you're seeking relaxation or exclusive outdoor adventures, the Caribbean is a fantastic destination for those seeking luxury entertainment.

  • 1. Jamaica

    Fall in love with this Caribbean Island and its lushly covered mountains, rainforests and reef-lined beaches with powdery white sand. From the renowned beaches of Negril to the island's breathtaking waterfalls with dizzying heights, the epic reggae music in laid-back towns to the legendary nightclubs and museums, this island is everything you imagined it to be.

  • 2. Barbados

    Located to the east of the Caribbean, this gorgeous coral island offers complete relaxation in a tropical setting. Enjoy swimming, kayaking, scuba diving and snorkeling in the calm waters. Take a catamaran cruise or explore the incredible network of caves that make up the Harrison Cave network.

  • 3. Martin

    Explore 37 pristine beaches on foot as you take in awe-inspiring scenery in St. Martin. The island boasts a thriving culinary scene with great restaurants overlooking the Caribbean Sea, as well as an array of duty-free shops for an unbeatable shopping experience. St. Martin has a lively entertainment scene with some of the best casinos and nightclubs in the Caribbean.

  • 4. Dominican Republic

    The Dominican Republic has a rich history evident in its stunning architecture. Its capital city, Santo Domingo, is lined with cobblestone streets and amazing restaurants. Indulge yourself in world-class scuba diving, snorkeling and diving experiences at heavenly beaches with crystal clear water.

Best Places to Stay for Luxury Holidays in the Caribbean

House Playa Chiquita
House ∙ 6 guests ∙ 3 bedrooms
Playa Chiquita, Sosúa, Dominican Republic
from $92
Vrbo
5.0/5.0
"Excellent"
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House St. Thomas
House ∙ 4 guests ∙ 2 bedrooms
St. Thomas, U.S. Virgin Islands
from $291
Vrbo
5.0/5.0
"Excellent"
View deal
House Le Moule
House ∙ 4 guests ∙ 2 bedrooms
Le Moule, Grande-Terre, Guadeloupe
from $95
Vrbo
5.0/5.0
"Excellent"
View deal
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