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
Oyster Bay Beach Resort
Oyster Pond
8.6/10 Excellent! (952 reviews)
Apr 16 - Apr 22
6 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,391, price is now $813 per person
$813
per person
found 1 day ago
Great service - from everyone we met. Really made the visit memorable
Reviewed on Jan 29, 2026
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,463 reviews)
Apr 16 - Apr 22
6 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Price was $2,412, price is now $1,024 per person
$1,024
per person
found 1 day ago
Great staff, comfortable rooms,walking distance to many restaurants....
Reviewed on Nov 10, 2025
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (973 reviews)
Apr 16 - Apr 22
6 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,653, price is now $854 per person
$854
per person
found 1 day ago
The room was spacious, clean and had adequate storage. The kitchenette was properly outfitted and they gave us a few complimentary drinks, The place was very quiet and private.
Reviewed on Nov 26, 2025
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,309 reviews)
Apr 16 - Apr 22
6 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,352, price is now $1,426 per person
$1,426
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (604 reviews)
Apr 16 - Apr 22
6 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,864, price is now $1,164 per person
$1,164
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
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
$471 nightly
The price is $516 total per night
$516 total
Mar 6 - Mar 7
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 luggage storage, 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 Punta Cana La Altagracia
131.05 mi from city center
$404 nightly
The price is $518 total per night
$518 total
Mar 1 - Mar 2
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 tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included
Serenade Punta Cana Beach & Spa Resort - All Inclusive
Carretera Cabeza de Toro Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
134.26 mi from city center
$360 nightly
The price is $461 total per night
$461 total
Mar 8 - Mar 9
Total with taxes and fees
Serenade Punta Cana Beach & Spa Resort - All Inclusive features a private beach, a full-service spa, and 3 outdoor pools. You can put free parking to good use if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this all-inclusive property include a free water park, a children's pool, and a gym.
On private beach
Pool
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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.
