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! (1,004 reviews)
Oct 24 - Oct 30
6 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,561, price is now $866 per person
$866
per person
found 1 day ago
My husband and I thoroughly enjoyed our stay. The staff was incredibly helpful and accommodating. I do wish we had more of a variety on the continental breakfast but other than that, it was fantastic! We’d absolutely stay again.
Reviewed on Aug 5, 2026
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (768 reviews)
Oct 24 - Oct 30
6 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,659, price is now $973 per person
$973
per person
found 1 day ago
nice place close to shops. good for relaxing
Reviewed on Aug 5, 2026
4.5-star property
Panorama Residences at Monte Vista
Point Blanche
9.6/10 Exceptional! (76 reviews)
Oct 24 - Oct 30
6 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,746, price is now $1,055 per person
$1,055
per person
found 1 day ago
It was an amazing property the pictures don’t do it justice. It’s 30 minutes from some popular spots but nice and quiet. Worth the drive if you ask me.
Reviewed on Aug 4, 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
$327 nightly
The price is $357 total per night
$357 total
Aug 19 - Aug 20
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 luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Free Cancellation
Reserve now, pay when you stay
301.79 mi from city center
$365 nightly
The price is $397 total per night
$397 total
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Regency Grand Reserve Puerto Rico features a golf course, a full-service spa, and 3 outdoor pools. Parking is USD 16.73 per night (USD 27.88 per night for valet parking)—but if you prefer not to drive, catch a ride in the airport shuttle (available 24 hours) for USD 96 per person roundtrip. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this spa resort include a children's pool, a 24-hour gym, and free WiFi in public areas.
Pool
Spa
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Playas de Bavaro Punta Cana La Altagracia
131.05 mi from city center
$269 nightly
The price is $344 total per night
$344 total
Sep 6 - Sep 7
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, tours or tickets, and luggage storage. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included
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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.
