Search for Cheap Deals on
Luxury & Trendy Hotels in Caribbean Islands

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!

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 $465 per night from Jan 26 to Jan 27
$465
includes taxes & fees
Jan 26 - Jan 27
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
Fully refundableReserve now, pay when you stay
  • 17 hours drive from Windward Islands
The price is $418 per night from Jan 29 to Jan 30
$418
includes taxes & fees
Jan 29 - Jan 30
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 $251 per night from Jan 26 to Jan 27
$251
includes taxes & fees
Jan 26 - Jan 27
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 $236 per night from Jan 21 to Jan 22
$236
includes taxes & fees
Jan 21 - Jan 22
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 $183 per night from Jan 24 to Jan 25
$183
includes taxes & fees
Jan 24 - Jan 25
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
Fully refundableReserve now, pay when you stay
  • 4 hours drive from Windward Islands
The price is $281 per night from Feb 4 to Feb 5
$281
includes taxes & fees
Feb 4 - Feb 5
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 27 to Jan 28
$502
includes taxes & fees
Jan 27 - Jan 28
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
Fully refundableReserve now, pay when you stay
  • 3 hours drive from Windward Islands
The price is $910 per night from Jan 27 to Jan 28
$910
includes taxes & fees
Jan 27 - Jan 28
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 $398 per night from Jan 21 to Jan 22
$398
includes taxes & fees
Jan 21 - Jan 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 ...
Get rates
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 ...
Get rates
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 24 to Jan 25
$799
includes taxes & fees
Jan 24 - Jan 25
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 79,135 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.