Caribbean Mountain Vacations
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Flight and Mountain hotel deals in Caribbean
Price found within the past 48 hours. Click for updated prices.
Strawberry Hill
CA $1,639
per person
Oct 25 - Oct 30
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
9.2/10 Wonderful! (179 reviews)
A beautiful hotel in an amazing location with stunning views over mountains and Kingston. Best rum punch ever! Karen runs a great hotel and was very helpful. We loved the gold disc room and the musical photos everywhere
Reviewed on Sep 22, 2026
5* Mountain holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
3 Night Mountain holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
Strawberry Hill
CA $1,001
per person
Nov 12 - Nov 15
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
9.2/10 Wonderful! (179 reviews)
A beautiful hotel in an amazing location with stunning views over mountains and Kingston. Best rum punch ever! Karen runs a great hotel and was very helpful. We loved the gold disc room and the musical photos everywhere
Reviewed on Sep 22, 2026
4 Night Mountain holidays in Caribbean
Price found within the past 48 hours. Click for updated prices.
Strawberry Hill
CA $1,375
per person
Dec 4 - Dec 8
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
9.2/10 Wonderful! (179 reviews)
A beautiful hotel in an amazing location with stunning views over mountains and Kingston. Best rum punch ever! Karen runs a great hotel and was very helpful. We loved the gold disc room and the musical photos everywhere
Reviewed on Sep 22, 2026
Mountain Hotels in Caribbean
Strawberry Hill
Island Outpost Irish Town Saint Andrew
CA $520
CA $626 total
Sep 25 - Sep 26
includes taxes & fees
Book a stay at this boutique hotel in Irish Town. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hardwar Gap and Catherine's Peak are ...
9.2/10 Wonderful! (186 reviews)
"A beautiful hotel in an amazing location with stunning views over mountains and Kingston. Best rum punch ever! Karen runs a great hotel and was very helpful. We loved the gold disc room and the musical photos everywhere"
Reviewed on Sep 22, 2026
Four Points by Sheraton Caguas Real Hotel & Casino
500 Alhambra En Granada Boulevard Caguas
CA $286
CA $371 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this golf hotel in Caguas. Enjoy free WiFi, a casino, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Ladera Resort - Adults Only
Rabot Estate Soufrière
Book a stay at this luxury resort in Soufrière. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
