Caribbean Islands Ski Vacations
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Top Ski vacation packages in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Price was ￥216,484, price is now ￥191,821 per person
￥191,821
per person
Feb 7 - Feb 10
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
Service and parking on the hotel was amazing. All amenities in the hotel were good. Very enjoyable time. Love to come back.
Reviewed on Dec 6, 2025
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View all trips3 Night Ski vacations in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Price was ￥216,484, price is now ￥191,821 per person
￥191,821
per person
Feb 7 - Feb 10
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
Service and parking on the hotel was amazing. All amenities in the hotel were good. Very enjoyable time. Love to come back.
Reviewed on Dec 6, 2025
Don't see what you're looking for?
See all available trips from Chicago to Caribbean Islands
View all tripsTop Ski Caribbean Islands Hotels
2 - Exotic Bungalow T2 & Large Garden near beach
LA TRINITE MARTINIQUE
Stay at this vacation home in La Trinité. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Plage des Raisiniers and Plage de l'Autre Bord ...
9.4/10 Exceptional! (15 reviews)
Beautiful Garden, convenience, comfortable, economical, perfect.
We were very pleased with the bungalow. We stayed 3 nights, 2/2/17 - 2/5/17, and would stay longer if we had more vacation time. We liked the outside but under cover dinning area. The kitchen was well stocked with all essentials. The climate controlled bedroom was adequate in size although we would ...
Reviewed on Feb 13, 2017
Bay Gardens Hotel
Rodney Bay Village Gros Islet
Book a stay at this beach hotel in Gros Islet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,007 reviews)
The room was clean and the staff were kind and friendly. The only downside was the unstable internet in the room.
Reviewed on Nov 27, 2025
Grand Bavaro Princess - All Inclusive
Playas De Bavaro Punta Cana La Altagracia
Book a stay at this luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (3,859 reviews)
Absolutely Beau we loved our stay at Grand Bavaro Princess
Reviewed on Dec 3, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
