
Caribbean Islands Vacation Packages
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4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,192 reviews)
Sep 20 - Sep 24
4 night stay
New York (JFK) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 21 hours ago
We love Simpson Bay Resort! Wonderful place to stay and excellent location!
Reviewed on Jul 5, 2025

4.0-star property
Oyster Bay Beach Resort
Oyster Pond
8.6/10 Excellent! (891 reviews)
Sep 13 - Sep 20
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Loved Oyster Bay resort. The room we stayed in was spacious and a bit worn but clean. The shower needs updating off the master and the water pressure was low. The staff were mostly friendly. The food was good except options limited on Valentine day dinner and Thurs buffet was not great for the amount of money charged the buffet food was very salty. But I would go back because the beach and views were spectacular! Shout out to the staff in Verandah for breakfast esp Shannon and the cab co affiliated esp Alex and Natalia they were very accommodating
Reviewed on Feb 17, 2025

3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (938 reviews)
Sep 13 - Sep 20
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Overall a great choice to stay
Reviewed on Feb 18, 2025

4.0-star property
Hilton Vacation Club Royal Palm St. Maarten
9/10 Wonderful! (1,048 reviews)
Sep 13 - Sep 20
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Loved the private beach area with umbrellas and chairs , pool area, restaurant on site with delicious breakfast and dinner options. The swim up bar was very enjoyable. The staff was sooooo friendly and our rooms were SPOTLESS. Gift shop on site was as good as going out shopping around… and the market on the premises has anything you forgot. We took family pics out on the beach one night. Only negative was the bar down the street you can hear the music late at night. But as far as this property…. BOOK IT!
Reviewed on Jun 21, 2025

4.0-star property
Divi Little Bay Beach Resort
8.4/10 Very Good! (1,003 reviews)
Sep 13 - Sep 20
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025
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 $441 total per night
$441 total
per night
Jul 23 - Jul 24
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

Fairmont El San Juan Hotel
6063 Isla Verde Avenue, Carolina
Free Cancellation
Reserve now, pay when you stay
287 mi from city center
The price is $469 total per night
$469 total
per night
Jul 14 - Jul 15
Fairmont El San Juan Hotel features a full-service spa, 4 outdoor pools, and a casino. Valet parking is available for USD 33.45 per day. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, concierge services, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a nightclub, a gym, and outdoor tennis courts.
Pool
Spa

Barceló Bávaro Beach - Adults Only - All Inclusive
Carretera Bávaro Km. 1, Playa Bávaro, Punta Cana, La Altagracia
131.28 mi from city center
The price is $312 total per night
$312 total
per night
Jul 16 - Jul 17
Barceló Bávaro Beach - Adults Only - All Inclusive features a golf course, a full-service spa, and a water park. There's free parking, as well as an airport shuttle for a fee (available on request). Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, tours or tickets, and securing valuables. Other amenities at this adults-only property include a nightclub, an outdoor pool, and a gym.
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.
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