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.
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (2,057 reviews)
Nov 25 - Nov 30
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Air Canada • Non-stop • Coach
Price was $2,421, price is now $1,127 per person
$1,127
per person
found 1 day ago
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,549 reviews)
Nov 14 - Nov 19
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,329, price is now $1,201 per person
$1,201
per person
found 1 day ago
4.0-star property
Sonesta Maho Beach All Inclusive Resort Casino & Spa
8/10 Very Good! (3,224 reviews)
Dec 2 - Dec 7
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Air Canada • Coach
Price was $2,457, price is now $1,623 per person
$1,623
per person
found 1 day ago
Everything was great
Reviewed on Sep 24, 2026
5.0-star property
Sonesta Ocean Point All Inclusive, Adults Only Resort
8.8/10 Excellent! (1,006 reviews)
Nov 2 - Nov 7
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $4,219, price is now $2,898 per person
$2,898
per person
found 1 day ago
The staff contributed to a more comfortable, friendly, and welcoming stay. Angela at the front desk was particularly helpful and professional, and Sharon at the restaurant made sure we were happy. I highly recommend Sonesta Ocean Point Resort for anyone's stay. And the food was amazing.
Reviewed on Sep 24, 2026
4.0-star property
The Morgan Resort Spa Village
9/10 Wonderful! (2,409 reviews)
Nov 25 - Nov 29
4 night stay
Cleveland (CLE) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Cleveland (CLE)
Southwest Airlines • Non-stop • Coach
Price was $2,153, price is now $1,494 per person
$1,494
per person
found 1 day ago
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
$263 nightly
The price is $337 total per night
$337 total
Oct 25 - Oct 26
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. Other amenities at this adults-only property 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.
