
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
Hilton Vacation Club Royal Palm St. Maarten
9/10 Wonderful! (1,048 reviews)
Oct 3 - Oct 6
3 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
I’ve been coming to this property for over 20 years and it far exceeds other properties on the island! Royal Palm has always and continues to update their rooms, beach and entire property which means they care, they put the customers first!!!
Reviewed on Jul 22, 2025

4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (563 reviews)
Oct 18 - Oct 24
6 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Copa • Non-stop • Coach
Save 100% on your flight
per person
found 19 hours ago
All the folks working at this property were great. The resort was nice but not pretentious.
Reviewed on Nov 18, 2024

4.0-star property
Oyster Bay Beach Resort
Oyster Pond
8.6/10 Excellent! (891 reviews)
Oct 12 - Oct 19
7 night stay
Detroit (DTW) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Detroit (DTW)
JetBlue Airways • Non-stop • Coach
per person
found 1 day ago
Beautiful area on St Maarten. Peaceful, serene, quiet, gorgeous views of the ocean, St Barts, and the mountains of the island
Reviewed on Jul 20, 2025

3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (938 reviews)
Oct 12 - Oct 19
7 night stay
Detroit (DTW) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Detroit (DTW)
JetBlue Airways • Non-stop • Coach
per person
found 1 day ago
Overall a great choice to stay
Reviewed on Feb 18, 2025

4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,192 reviews)
Oct 16 - Oct 20
4 night stay
New York (JFK) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
We love Simpson Bay Resort! Wonderful place to stay and excellent location!
Reviewed on Jul 5, 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
$357 nightly
The price is $393 total per night
$393 total
Aug 25 - Aug 26
Total includes 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, Higuey, Punta Cana, La Altagracia
Free Cancellation
Reserve now, pay when you stay
131.05 mi from city center
$403 nightly
The price is $475 total per night
$475 total
Aug 17 - Aug 18
Total includes 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, luggage storage, and tours or tickets. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included

Fairmont El San Juan Hotel
6063 Isla Verde Avenue, Carolina
Free Cancellation
Reserve now, pay when you stay
287 mi from city center
$422 nightly
The price is $469 total per night
$469 total
Jul 27 - Jul 28
Total includes taxes and fees
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
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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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