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Luxury & Trendy Hotels in Caribbean Islands

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Hotels in Caribbean Islands

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
4 out of 5
  • 17 hours drive from Windward Islands
The price is $388 per night from Dec 22 to Dec 23
$388
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star luxury hotel in San Juan. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Aire de O:live
Aire de O:live
4 out of 5
  • 17 hours drive from Windward Islands
The price is $445 per night from Jan 13 to Jan 14
$445
includes taxes & fees
Jan 13 - Jan 14, 2025
Stay at this 4-star beach hotel in Carolina. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the helpful staff and the clean rooms in our ...
Aire de O:live
Villa Herencia Hotel
Villa Herencia Hotel
3.5 out of 5
Fully refundableReserve now, pay when you stay
  • 17 hours drive from Windward Islands
The price is $236 per night from Dec 22 to Dec 23
$236
includes taxes & fees
Dec 22 - Dec 23
Stay at this 3.5-star boutique hotel in San Juan. Enjoy free WiFi, daily housekeeping, and a garden. Our guests praise the helpful staff in our reviews. Popular ...
Villa Herencia Hotel
Billini Hotel, Historic Luxury
Billini Hotel, Historic Luxury
4.5 out of 5
Fully refundableReserve now, pay when you stay
  • 23 hours drive from Windward Islands
The price is $265 per night from Jan 4 to Jan 5
$265
includes taxes & fees
Jan 4 - Jan 5, 2025
Stay at this 4.5-star luxury hotel in Santo Domingo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Billini Hotel, Historic Luxury
Wonders Boutique Hotel
Wonders Boutique Hotel
3.5 out of 5
  • 19 hours drive from Windward Islands
The price is $179 per night from Dec 21 to Dec 22
$179
includes taxes & fees
Dec 21 - Dec 22
Stay at this 3.5-star beach hotel in Oranjestad. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our ...
Wonders Boutique Hotel
True Blue Bay Resort
True Blue Bay Resort
4 out of 5
  • 4 hours drive from Windward Islands
The price is $367 per night from Jan 6 to Jan 7
$367
includes taxes & fees
Jan 6 - Jan 7, 2025
Stay at this 4-star spa resort in St. George's. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff and the property condition ...
True Blue Bay Resort
Hotel El Convento
Hotel El Convento
4.5 out of 5
Fully refundableReserve now, pay when you stay
  • 17 hours drive from Windward Islands
The price is $502 per night from Jan 6 to Jan 7
$502
includes taxes & fees
Jan 6 - Jan 7, 2025
Stay at this 4.5-star luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Hotel El Convento
Waves Hotel & Spa by Elegant Hotels - All Inclusive
Waves Hotel & Spa by Elegant Hotels - All Inclusive
4 out of 5
  • 3 hours drive from Windward Islands
The price is $910 per night from Jan 7 to Jan 8
$910
includes taxes & fees
Jan 7 - Jan 8, 2025
Stay at this 4-star beach property in Prospect. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Waves Hotel & Spa by Elegant Hotels - All Inclusive
Sandy Haven Resort
Sandy Haven Resort
4 out of 5
Fully refundableReserve now, pay when you stay
  • 37 hours drive from Windward Islands
The price is $215 per night from Dec 21 to Dec 22
$215
includes taxes & fees
Dec 21 - Dec 22
Stay at this 4-star beach hotel in Negril. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
Sandy Haven Resort
Marquis Boutique Hotel
Marquis Boutique Hotel
  • 13 hours drive from Windward Islands
Book a stay at this boutique resort in Anse Marcel. Enjoy free WiFi, free parking, and a marina. Popular attractions Orient Bay Beach and Anse Marcel Beach are ...
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Marquis Boutique Hotel
Sugar Ridge
Sugar Ridge
4 out of 5
  • 10 hours drive from Windward Islands
Stay at this 4-star spa hotel in Jolly Harbour. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Jolly Beach and Valley Church Beach ...
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Sugar Ridge
Mount Cinnamon Grenada
Mount Cinnamon Grenada
4 out of 5
  • 4 hours drive from Windward Islands
The price is $799 per night from Jan 6 to Jan 7
$799
includes taxes & fees
Jan 6 - Jan 7, 2025
Stay at this 4-star beach hotel in St. George's. Enjoy free breakfast, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. ...
Mount Cinnamon Grenada
See all 78,970 properties in Caribbean Islands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.