Caribbean Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
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Top Ski vacation packages in Caribbean
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Price was $916, price is now $684 per person
$684
per person
Mar 5 - Mar 8
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
Amazing property with beautiful views. Food was better than expected and staff was extremely courteous and friendly. Our stay was memorable and one we would love to repeat. If I was to make suggestions I would say: have an adult pool, or a more quiet area; gym is too small, you could add a studio using the closed stores beside the gym; offer water by the tennis courts and refill the coolers by the pickleball courts.
Reviewed on Jan 2, 2026
Bahia Principe Fantasia Punta Cana - All Inclusive
Bávaro
Save 100% on your flight
Price was $1,464, price is now $830 per person
$830
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Punta Cana (PUJ)
8.4/10 Very Good! (2,391 reviews)
Weak service, terrible food, too much noise, limited dining options, wasn’t able to reserve any a la carte restaurants throughout the entire stay. ( always overbooked) couldn’t wait to get out of there 👎👎
Reviewed on Dec 30, 2025
Grand Bavaro Princess - All Inclusive
Bávaro
Save 100% on your flight
Price was $6,051, price is now $4,317 per person
$4,317
per person
Mar 7 - Mar 14
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Punta Cana (PUJ)
8.2/10 Very Good! (3,836 reviews)
Love the room and the beach!
Reviewed on Jan 1, 2026
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
Save 100% on your flight
Price was $2,101, price is now $1,515 per person
$1,515
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Vieux Fort (UVF)
8.4/10 Very Good! (123 reviews)
Friendly and personable staff. Food was decent with the Japanese restaurant being the highlight. However, expect "island time" services. Lots of options for lunch buffet. Room was great, comfortable and modern. Pool was good with fun activities provided by staff. Overall would recommend and stay again only at the same rate as the value from booking in Sept and staying during xmas was a great deal.
Reviewed on Dec 30, 2025
5* Ski vacations in Caribbean
Price found within the past 48 hours. Click for updated prices.
Grand Bavaro Princess - All Inclusive
Bávaro
Save 100% on your flight
Price was $6,051, price is now $4,317 per person
$4,317
per person
Mar 7 - Mar 14
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Punta Cana (PUJ)
8.2/10 Very Good! (3,836 reviews)
Love the room and the beach!
Reviewed on Jan 1, 2026
3 Night Ski vacations in Caribbean
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Save 100% on your flight
Price was $780, price is now $534 per person
$534
per person
Feb 2 - Feb 5
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
Amazing property with beautiful views. Food was better than expected and staff was extremely courteous and friendly. Our stay was memorable and one we would love to repeat. If I was to make suggestions I would say: have an adult pool, or a more quiet area; gym is too small, you could add a studio using the closed stores beside the gym; offer water by the tennis courts and refill the coolers by the pickleball courts.
Reviewed on Jan 2, 2026
Bahia Principe Fantasia Punta Cana - All Inclusive
Bávaro
Save 100% on your flight
Price was $1,464, price is now $830 per person
$830
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Punta Cana (PUJ)
8.4/10 Very Good! (2,391 reviews)
Weak service, terrible food, too much noise, limited dining options, wasn’t able to reserve any a la carte restaurants throughout the entire stay. ( always overbooked) couldn’t wait to get out of there 👎👎
Reviewed on Dec 30, 2025
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
Save 100% on your flight
Price was $2,101, price is now $1,515 per person
$1,515
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Vieux Fort (UVF)
8.4/10 Very Good! (123 reviews)
Friendly and personable staff. Food was decent with the Japanese restaurant being the highlight. However, expect "island time" services. Lots of options for lunch buffet. Room was great, comfortable and modern. Pool was good with fun activities provided by staff. Overall would recommend and stay again only at the same rate as the value from booking in Sept and staying during xmas was a great deal.
Reviewed on Dec 30, 2025
4 Night Ski vacations in Caribbean
Price found within the past 48 hours. Click for updated prices.
El Conquistador Resort
Cabezas
Save 100% on your flight
Price was $1,106, price is now $737 per person
$737
per person
Feb 2 - Feb 6
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to San Juan (SJU)
9/10 Wonderful! (3,205 reviews)
Amazing property with beautiful views. Food was better than expected and staff was extremely courteous and friendly. Our stay was memorable and one we would love to repeat. If I was to make suggestions I would say: have an adult pool, or a more quiet area; gym is too small, you could add a studio using the closed stores beside the gym; offer water by the tennis courts and refill the coolers by the pickleball courts.
Reviewed on Jan 2, 2026
Bahia Principe Fantasia Punta Cana - All Inclusive
Bávaro
Save 100% on your flight
Price was $1,898, price is now $1,052 per person
$1,052
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Cana (PUJ)
8.4/10 Very Good! (2,391 reviews)
Weak service, terrible food, too much noise, limited dining options, wasn’t able to reserve any a la carte restaurants throughout the entire stay. ( always overbooked) couldn’t wait to get out of there 👎👎
Reviewed on Dec 30, 2025
Planning your Caribbean ski vacation
What are some things I should consider when booking a Caribbean ski trip package?
Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.
How can I find cheap Caribbean ski packages?
Right now, ski trips start at just $534. Prices and availability are subject to change. Additional terms may apply.
Can I book a beginner ski package in Caribbean?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Caribbean. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.
How much does a ski trip to Caribbean cost?
Sensational ski trips to Caribbean start from $534. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.
When’s the best time of year to plan a ski trip to Caribbean?
The best time to hit the slopes in Caribbean depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.
Can I book Caribbean ski packages with airfare?
Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.
Can I book a Caribbean ski trip with free cancellation and/or flexible dates?
Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.
Why should I book a ski package in Caribbean with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Caribbean ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.
Top Ski Caribbean 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
$123 nightly
The price is $137 total per night from Jan 5 to Jan 6
$137 total
Jan 5 - Jan 6
Total with taxes and fees
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! (1,010 reviews)
Clean room | courtesy Staff
Reviewed on Jan 1, 2026
Grand Bavaro Princess - All Inclusive
Playas De Bavaro Punta Cana La Altagracia
$297 nightly
The price is $380 total per night from Jan 6 to Jan 7
$380 total
Jan 6 - Jan 7
Total with taxes and fees
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! (3,880 reviews)
Love the room and the beach!
Reviewed on Jan 1, 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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
