
Caribbean Islands Vacation Packages
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3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (966 reviews)
Nov 30 - Dec 4
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,122, price is now $771 per person
$771
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! (1,398 reviews)
Dec 8 - Dec 15
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,948, price is now $979 per person
$979
per person
found 21 hours ago
Stay at Simpson Bay studio suite turned out to actually be in steep, uphill Royal resort bldg with no view of water, not close to beach and room itself faced parking lot. Room was clean, although the water faucets for some reason leaked, and the most annoying part of stay was that you needed to walk to a “towel booth” near the security booth to get clean towels, rather than having them available by pool. Parking was luckily available, and renting a car would be needed for this hotel, as well as for ease in getting around.
Reviewed on Oct 18, 2025

4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,268 reviews)
Jan 5 - Jan 9
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,148, price is now $1,197 per person
$1,197
per person
found 1 day ago
The resort grounds are beautiful and immaculately maintained! All the staff were friendly and helpful. The room was very clean and had plenty of amenities. A very nice stay for the money!
Reviewed on Oct 8, 2025

4.0-star property
Esmeralda Resort
8.6/10 Excellent! (465 reviews)
Dec 8 - Dec 15
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,728, price is now $1,239 per person
$1,239
per person
found 21 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
Hilton Vacation Club Flamingo Beach St. Maarten
Pelican Key
9/10 Wonderful! (1,278 reviews)
Nov 26 - Nov 30
4 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Sterling Blue • Non-stop • Coach
Price was $1,290, price is now $933 per person
$933
per person
found 1 day ago
Friendly staff
Great room
Clean
Reviewed on Sep 9, 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
$439 nightly
The price is $483 total per night
$483 total
Oct 29 - Oct 30
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 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
$336 nightly
The price is $430 total per night
$430 total
Oct 26 - Oct 27
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, dry cleaning/laundry, and luggage storage. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included

Hotel Riu Republica - Adults only - All Inclusive
Playa Arena Gorda, Punta Cana
126.6 mi from city center
Hotel Riu Republica - Adults only - All Inclusive features a free water park, a nightclub, and an outdoor pool. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this adults-only property include a gym, a steam room, and free WiFi in public areas.
Pool
Hot Tub
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