
Caribbean Islands Vacation Packages
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3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (927 reviews)
Aug 18 - Aug 25
7 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop 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
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,171 reviews)
Jul 27 - Jul 31
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The property was very nice, clean and beautiful. The beach area was very nice with huts for shade. Plenty of chairs to relax in. The pool area was cleaned everyday and not crowded. The jewelry shop owner was the nicest man. Easy to talk to with no pressure to purchase anything. Several restaurants with good food and drinks I would definitely come back to this resorts.
Reviewed on Jun 8, 2025

4.0-star property
Hilton Vacation Club Royal Palm St. Maarten
9/10 Wonderful! (1,031 reviews)
Aug 18 - Aug 25
7 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Great 3 bedroom option with full kitchen. Very walkable.
Reviewed on Jan 2, 2025


4.0-star property
Oyster Bay Beach Resort
Oyster Pond
8.6/10 Excellent! (874 reviews)
Aug 18 - Aug 25
7 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop 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
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
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 tours or tickets, securing valuables, and luggage storage. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa

Barceló Bávaro Palace - All Inclusive
Carretera Bávaro Km. 1, Playa Bávaro, Punta Cana, La Altagracia
131.27 mi from city center
Barceló Bávaro Palace - All Inclusive features a private beach, a golf course, and a full-service spa. You can take advantage of free parking, along with an area shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, securing valuables, and dry cleaning/laundry. Other amenities at this all-inclusive property include 4 outdoor pools, a water park, and a nightclub.
On private beach
Pool

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
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, luggage storage, and securing valuables. Other amenities at this beach resort include a children's pool, a 24-hour gym, and a sauna.
Pool
Hot Tub
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