Caribbean Islands Vacation Packages
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Top Caribbean Islands vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,000 reviews)
Dec 8 - Dec 15
7 night stay
Cleveland (CLE) to Philipsburg (SXM)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,719, price is now $1,004 per person
$1,004
per person
found 1 day ago
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.
Reviewed on Sep 14, 2026
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (2,057 reviews)
Nov 13 - Nov 18
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $2,341, price is now $1,053 per person
$1,053
per person
found 1 day ago
The beach bar with mayling the best bartender waitress!!!
Reviewed on Sep 25, 2026
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,549 reviews)
Nov 7 - Nov 14
7 night stay
Cleveland (CLE) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,136, price is now $1,490 per person
$1,490
per person
found 3 hours ago
4.0-star property
The Morgan Resort Spa Village
9/10 Wonderful! (2,409 reviews)
Dec 8 - Dec 15
7 night stay
Cleveland (CLE) to Philipsburg (SXM)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,766, price is now $1,636 per person
$1,636
per person
found 1 day ago
Nice hotel! We will be coming back to stay :)
Reviewed on Sep 25, 2026
4.0-star property
Divi Little Bay Beach Resort
8.2/10 Very Good! (1,007 reviews)
Dec 8 - Dec 15
7 night stay
Cleveland (CLE) to Philipsburg (SXM)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,237, price is now $1,400 per person
$1,400
per person
found 1 day ago
.
Reviewed on Sep 24, 2026
Top rated hotels for your Caribbean Islands vacation package
Grand Hyatt Baha Mar
One Baha Mar Boulevard Nassau New Providence
Free Cancellation
Reserve now, pay when you stay
637 mi from city center
$345 nightly
The price is $378 total per night
$378 total
Oct 18 - Oct 19
Total with taxes and fees
Grand Hyatt Baha Mar features a golf course, a full-service spa, and 8 outdoor pools. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, tours or tickets, and securing valuables. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Playas de Bavaro Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
131.05 mi from city center
$251 nightly
The price is $321 total per night
$321 total
Oct 27 - Oct 28
Total with taxes and fees
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive features a full-service spa, 5 outdoor pools, and a free water park. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, dry cleaning/laundry, and luggage storage. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included
Hotel Riu Montego Bay - Adults Only - All Inclusive
Mahoe Bay, Ironshore Montego Bay Saint James
489.91 mi from city center
Hotel Riu Montego Bay - Adults Only - All Inclusive features a full-service spa, 5 outdoor pools, and a free water park. Free parking is included with your stay. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a nightclub, a gym, and a sauna.
Pool
Hot Tub
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View all propertiesLowest 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.
