
Caribbean Islands Vacation Packages
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3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (938 reviews)
Oct 6 - Oct 11
5 night stay
Detroit (DTW) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
Overall a great choice to stay
Reviewed on Feb 18, 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
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per person
found 1 day 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
Esmeralda Resort
8.6/10 Excellent! (463 reviews)
Oct 6 - Oct 11
5 night stay
Detroit (DTW) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
The Esmeralda Resort/Spa is an ideal place for those that like a quiet, detached, peaceful, and less crowded type setting. Its situated behind a beach bar at the north end of the bay. Cabins of 4 units share their own pool, thus making it quite cozy and private to lounge in your "own pool". The restaurant is fantastic for the quality of the food and its staff. The staff were extremely helpful, friendly, and as a single traveler, they engaged in conversation but not too much so seem invasive. Do not mistake the restaurant for being low cost--it was not. It can be on the pricy end to dine there, yet well worth it. The included continental brunch, was sort of blah, as there is nothing but carbs, and more carbs to eat. A small bowl of fruit is provided, along with 2 types of cereal, teas and coffee. If eggs or meats or anything else beyond bread (too much bread) is desired, then there is a menue available for those items at a cost. I highly recommend Esmeralda and would gladly stay again.
Reviewed on Apr 7, 2025

4.0-star property
Oceans at Divi Little Bay
8.4/10 Very Good! (238 reviews)
Oct 6 - Oct 11
5 night stay
Detroit (DTW) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
Oceans is beautiful. The property is well maintained, clear water, very nice beach. Food and drinks were very good . The view from the 2nd floor is wonderful. Fort Amsterdam is a must see. Watching the cruise ships come into the port was cool. I highly recommend staying here. The all inclusive option is well worth it. Its a very safe island, we recommend renting a car and exploring the island. We will return to Oceans
Reviewed on Sep 26, 2024

4.0-star property
Hilton Vacation Club Royal Palm St. Maarten
9/10 Wonderful! (1,048 reviews)
Oct 6 - Oct 11
5 night stay
Detroit (DTW) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 hour 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
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 26 - Aug 27
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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