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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
Fully refundableReserve now, pay when you stay
  • 17 hours drive from Windward Islands
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. ...
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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
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 ...
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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
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 ...
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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
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. ...
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Billini Hotel, Historic Luxury
Wonders Boutique Hotel
Wonders Boutique Hotel
3.5 out of 5
  • 19 hours drive from Windward Islands
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 ...
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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
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 ...
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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
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 ...
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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
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 ...
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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
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 ...
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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 Grand Case Beach are ...
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Marquis Boutique Hotel
Mount Cinnamon Grenada
Mount Cinnamon Grenada
4 out of 5
  • 4 hours drive from Windward Islands
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. ...
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Mount Cinnamon Grenada
DREAMCATCHER by DW - ADULTS ONLY
DREAMCATCHER by DW - ADULTS ONLY
3.5 out of 5
Fully refundableReserve now, pay when you stay
  • 17 hours drive from Windward Islands
Stay at this 3.5-star beach hotel in San Juan. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
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DREAMCATCHER by DW - ADULTS ONLY
See all 81,183 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.