Caribbean Islands Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Ski vacation packages in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.
Grand Bavaro Princess - All Inclusive
Bávaro
Price was ￥88,897, price is now ￥88,897 per person
￥88,897
per person
Mar 26 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Punta Cana (PUJ)
8.2/10 Very Good! (3,836 reviews)
Room had not pillow and blankets for the 3rd person. Very damp. Bed sheets felt humid and towels wouldn't dry. Musty smell in the room. 2 people out of 3 were sick on the third day. Ground, beach and ocean were very nice and staff are very helpful and polite.
Reviewed on Feb 5, 2026
El Conquistador Resort
Cabezas
Price was ￥385,981, price is now ￥353,870 per person
￥353,870
per person
Mar 10 - Mar 13
found 9 hours ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
The room was spotless and the views were amazing. The staff was beyond friendly. We had the most fabulous time and will return!
Reviewed on Feb 4, 2026
Don't see what you're looking for?
See all available trips from Calgary to Caribbean Islands
View all trips5* Ski vacations in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.
Grand Bavaro Princess - All Inclusive
Bávaro
Price was ￥88,897, price is now ￥88,897 per person
￥88,897
per person
Mar 26 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Punta Cana (PUJ)
8.2/10 Very Good! (3,836 reviews)
Room had not pillow and blankets for the 3rd person. Very damp. Bed sheets felt humid and towels wouldn't dry. Musty smell in the room. 2 people out of 3 were sick on the third day. Ground, beach and ocean were very nice and staff are very helpful and polite.
Reviewed on Feb 5, 2026
Don't see what you're looking for?
See all available trips from Calgary to Caribbean Islands
View all trips3 Night Ski vacations in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.
Grand Bavaro Princess - All Inclusive
Bávaro
Price was ￥88,897, price is now ￥88,897 per person
￥88,897
per person
Mar 26 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Punta Cana (PUJ)
8.2/10 Very Good! (3,836 reviews)
Room had not pillow and blankets for the 3rd person. Very damp. Bed sheets felt humid and towels wouldn't dry. Musty smell in the room. 2 people out of 3 were sick on the third day. Ground, beach and ocean were very nice and staff are very helpful and polite.
Reviewed on Feb 5, 2026
Don't see what you're looking for?
See all available trips from Calgary to Caribbean Islands
View all trips4 Night Ski vacations in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Price was ￥385,981, price is now ￥353,870 per person
￥353,870
per person
Mar 10 - Mar 13
found 9 hours ago
Roundtrip flight included
Osaka (OSA) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
The room was spotless and the views were amazing. The staff was beyond friendly. We had the most fabulous time and will return!
Reviewed on Feb 4, 2026
Don't see what you're looking for?
See all available trips from Osaka 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! (1,006 reviews)
Excellent
Reviewed on Feb 1, 2026
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! (3,896 reviews)
The staff was very nice. The beach was awesome.
Reviewed on Feb 3, 2026
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.
