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

Strawberry Hill

CA $1,602
per person
Sep 7 - Sep 11
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
9.2/10 Wonderful! (172 reviews)
Ladera Resort - Adults Only

Ladera Resort - Adults Only

CA $2,783
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Vieux Fort (UVF)
9.8/10 Exceptional! (708 reviews)
Amazing everything! Staff, food, views!

Reviewed on Aug 6, 2026

Rabot Hotel from Hotel Chocolat

Rabot Hotel from Hotel Chocolat

CA $1,841
per person
Sep 7 - Sep 11
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Vieux Fort (UVF)
9.4/10 Exceptional! (699 reviews)
It was amazing!

Reviewed on Aug 5, 2026

Montpelier Nevis

Montpelier Nevis

CA $3,460
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newcastle (NEV)
9.8/10 Exceptional! (173 reviews)
I’ve travelled all across the Caribbean and the Montpellier hotel is by far the best I’ve stayed at. That is mostly due to the staff who are so friendly and catered to our every need within the hotel, and ensuring all our excursions from the hotel ran smoothly. I hope to return to Montpellier soon.

Reviewed on Aug 8, 2026

Caille Blanc Villa & Hotel - Adults Only

Caille Blanc Villa & Hotel - Adults Only

CA $2,318
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Vieux Fort (UVF)
9.6/10 Exceptional! (157 reviews)
The view was absolutely beautiful. The villa was very quiet and peaceful being right by the water. The staff were incredibly sweet and helpful. We really enjoyed our stay and the excursions that were available through our hotel.

Reviewed on Aug 3, 2026

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5* Mountain holidays in Caribbean

Price found within the past 48 hours. Click for updated prices.
Ladera Resort - Adults Only

Ladera Resort - Adults Only

CA $2,783
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Vieux Fort (UVF)
9.8/10 Exceptional! (708 reviews)
Amazing everything! Staff, food, views!

Reviewed on Aug 6, 2026

Don't see what you're looking for?
See all available trips from Columbus to Caribbean
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3 Night Mountain holidays in Caribbean

Price found within the past 48 hours. Click for updated prices.
Strawberry Hill

Strawberry Hill

CA $1,031
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Kingston (KIN)
9.2/10 Wonderful! (172 reviews)
Ladera Resort - Adults Only

Ladera Resort - Adults Only

CA $2,783
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Vieux Fort (UVF)
9.8/10 Exceptional! (708 reviews)
Amazing everything! Staff, food, views!

Reviewed on Aug 6, 2026

Caille Blanc Villa & Hotel - Adults Only

Caille Blanc Villa & Hotel - Adults Only

CA $2,197
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Vieux Fort (UVF)
9.6/10 Exceptional! (157 reviews)
The view was absolutely beautiful. The villa was very quiet and peaceful being right by the water. The staff were incredibly sweet and helpful. We really enjoyed our stay and the excursions that were available through our hotel.

Reviewed on Aug 3, 2026

Don't see what you're looking for?
See all available trips from Columbus to Caribbean
View all trips

4 Night Mountain holidays in Caribbean

Price found within the past 48 hours. Click for updated prices.
Strawberry Hill

Strawberry Hill

CA $1,267
per person
Oct 8 - Oct 12
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
9.2/10 Wonderful! (172 reviews)
Ladera Resort - Adults Only

Ladera Resort - Adults Only

CA $3,229
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Vieux Fort (UVF)
9.8/10 Exceptional! (708 reviews)
Amazing everything! Staff, food, views!

Reviewed on Aug 6, 2026

Rabot Hotel from Hotel Chocolat

Rabot Hotel from Hotel Chocolat

CA $1,875
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Vieux Fort (UVF)
9.4/10 Exceptional! (699 reviews)
It was amazing!

Reviewed on Aug 5, 2026

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Mountain Hotels in Caribbean

Strawberry Hill

Strawberry Hill

Island Outpost Irish Town Saint Andrew
CA $469
CA $564 total
Aug 10 - Aug 11
includes taxes & fees
Book a stay at this boutique hotel in Irish Town. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bob Marley Museum and Hardwar Gap are ...
Strawberry Hill
Four Points by Sheraton Caguas Real Hotel & Casino

Four Points by Sheraton Caguas Real Hotel & Casino

500 Alhambra En Granada Boulevard Caguas
CA $283
CA $368 total
Aug 18 - Aug 19
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 ...
8.8/10 Excellent! (1,005 reviews)
"Espectacular tranquilo accesible tiene lo necesario desde un descaso hasta buena gastronomía"

Reviewed on Aug 8, 2026

Four Points by Sheraton Caguas Real Hotel & Casino
Ladera Resort - Adults Only

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 ...
9.8/10 Exceptional! (712 reviews)
"Amazing everything! Staff, food, views!"

Reviewed on Aug 6, 2026

Get rates
Ladera Resort - Adults Only
See all 88,662 properties in Caribbean
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.