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! (1,987 reviews)
Nov 5 - Nov 9
4 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
JetBlue Airways • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,836, price is now $858 per person
$858
per person
found 1 day ago
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,525 reviews)
Oct 24 - Oct 28
4 night stay
Atlanta (ATL) to Philipsburg (SXM)
Delta • Coach
Philipsburg (SXM) to Atlanta (ATL)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,693, price is now $893 per person
$893
per person
found 1 day ago
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,000 reviews)
Oct 24 - Oct 28
4 night stay
Atlanta (ATL) to Philipsburg (SXM)
Delta • Coach
Philipsburg (SXM) to Atlanta (ATL)
JetBlue Airways • Coach
Price was $1,243, price is now $889 per person
$889
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
La Playa Orient Bay
9.4/10 Exceptional! (786 reviews)
Oct 24 - Oct 28
4 night stay
Atlanta (ATL) to Philipsburg (SXM)
Delta • Coach
Philipsburg (SXM) to Atlanta (ATL)
JetBlue Airways • Coach
Price was $1,308, price is now $957 per person
$957
per person
found 1 day ago
We got a room upgrade upon arrival and it was beautiful! The property is spotless, easy access to the beach and all good restaurants. Plan to come back in the near future.
Reviewed on Sep 18, 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 4 - Oct 5
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
$299 nightly
The price is $382 total per night
$382 total
Oct 18 - Oct 19
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.
