Caribbean Islands Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Caribbean Islands vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel La Plantation
8.8/10 Excellent! (563 reviews)
Oct 30 - Nov 2
3 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Price was $861, price is now $760 per person
$760
per person
found 1 day ago
Our rooms were ready as soon as we arrived. They were so spacious, clean, comfortable and as close to the beach as requested. Pool was open until 10 which was great for my kids. 5 min walk to the beach, shops, restaurants, market and everything else you can use. Breakfast was a little basic (eggs, bacon, cereal, etc) but we had fresh fruit, juices & croissants. Overall we couldn’t complain about anything and would stay here again if we visit the island
Reviewed on Jul 31, 2025
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (587 reviews)
Oct 20 - Oct 25
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,280, price is now $862 per person
$862
per person
found 18 hours ago
All the folks working at this property were great. The resort was nice but not pretentious.
Reviewed on Nov 18, 2024
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
The price is $356 total per night
$356 total
per night
Aug 27 - Aug 28
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 concierge services, luggage storage, and securing valuables. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Hyatt Vacation Club at Hacienda del Mar, Dorado
301 Hwy 693, Dorado, Vega Alta
Free Cancellation
267.23 mi from city center
The price is $198 total per night
$198 total
per night
Sep 25 - Sep 26
Hyatt Vacation Club at Hacienda del Mar, Dorado features an outdoor pool, a children's pool, and a gym. The front desk has multilingual staff that can help with securing valuables and dry cleaning/laundry. Other amenities at this beach resort include free WiFi in public areas, a hot tub, and laundry facilities.
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Playas de Bavaro, Higuey, Punta Cana, La Altagracia
131.05 mi from city center
The price is $430 total per night
$430 total
per night
Sep 1 - Sep 2
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 tours or tickets, securing valuables, and luggage storage. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Caribbean Islands
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.
More trip options
Top trending
Hotels
Flights
- Cheap New York to Antigua flights
- Cheap Boston to St. Thomas flights
- Cheap Flights from Puerto Rico Island
- Cheap Atlanta to St. Thomas and St. John flights
- Cheap Flights to Hispaniola
- Cheap Miami to St. Barthelemy flights
- Cheap Flights to Bonaire
- Cheap Flights to St. Croix Island
- Cheap Kingston to Antigua flights
- Cheap Flights to St. Thomas
- Cheap Flights to Grand Cayman
- Cheap Flights to St. Thomas and St. John
- Cheap Kingston to Grand Cayman flights
- Cheap San Juan to St. Thomas flights