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.
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (973 reviews)
Jan 22 - Jan 27
5 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,450, price is now $891 per person
$891
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
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,463 reviews)
Mar 7 - Mar 11
4 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Price was $2,099, price is now $999 per person
$999
per person
found 1 day ago
Great staff, comfortable rooms,walking distance to many restaurants....
Reviewed on Nov 10, 2025
4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,309 reviews)
Mar 7 - Mar 11
4 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Price was $2,306, price is now $1,172 per person
$1,172
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025
4.0-star property
Oceans at Divi Little Bay
8.4/10 Very Good! (266 reviews)
Mar 7 - Mar 11
4 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,942, price is now $1,230 per person
$1,230
per person
found 1 day ago
Great property for families
Reviewed on Jul 31, 2025
4.0-star property
Divi Little Bay Beach Resort
8.4/10 Very Good! (1,002 reviews)
Mar 7 - Mar 11
4 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,809, price is now $1,156 per person
$1,156
per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025
Top rated hotels for your Caribbean Islands vacation package
Grand Hyatt Baha Mar
One Baha Mar Boulevard Nassau New Providence
637 mi from city center
$471 nightly
The price is $516 total per night
$516 total
Jan 6 - Jan 7, 2026
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 securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa
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 concierge services, dry cleaning/laundry, 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
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
Jan 11 - Jan 12, 2026
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 luggage storage, securing valuables, and tours or tickets. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included
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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.
