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 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
Beach area was so nice , love how many pools there were , shuttles came very quickly
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
just found
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,000 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 $1,940, price is now $1,269 per person
$1,269
per person
just found
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
Coral Beach Club Villas & Marina
Oyster Pond
9.2/10 Wonderful! (119 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 $3,924, price is now $2,705 per person
$2,705
per person
just found
The condo and property was clean and well decorated and maintained. We had an awesome stay and will return.
Reviewed on Jul 19, 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. 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.
