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
Hotel La Plantation
8.8/10 Excellent! (624 reviews)
Aug 27 - Aug 31
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Price was $989, price is now $687 per person
$687
per person
found 24 hours ago
Our rooms were ready as soon as we arrived. They were so spacious, clean, comfortable and as close to the beach as requested. Pool was open until 10 which was great for my kids. 5 min walk to the beach, shops, restaurants, market and everything else you can use. Breakfast was a little basic (eggs, bacon, cereal, etc) but we had fresh fruit, juices & croissants. Overall we couldn’t complain about anything and would stay here again if we visit the island
Reviewed on Jul 31, 2025
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,426 reviews)
Aug 6 - Aug 10
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,841, price is now $914 per person
$914
per person
found 1 day ago
the view from our balcony is always fabulous. the beach bar and palapas are very nice . we can walk to dinner every night to a different restaurant. we have stayed at simpson bay villas at least 5 times and love it.
Reviewed on Jun 19, 2026
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,780 reviews)
Aug 6 - Aug 10
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,546, price is now $820 per person
$820
per person
found 1 day ago
Nice beach, nice staff. Only gripe is charging to use the gym - come on, that’s cheap
Reviewed on Mar 7, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,004 reviews)
Aug 6 - Aug 10
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Price was $1,034, price is now $707 per person
$707
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
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
$405 nightly
The price is $443 total per night
$443 total
Jun 29 - Jun 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
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
$232 nightly
The price is $297 total per night
$297 total
Jul 7 - Jul 8
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 take advantage of free parking, along with a theme park shuttle. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this all-inclusive property include a free water park, a nightclub, and karaoke.
On private beach
Pool
Ocean Blue & Sand Beach Resort - All Inclusive
Car. Arena Gorda Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
128.45 mi from city center
$396 nightly
The price is $396 total per night
$396 total
Jul 1 - Jul 2
Total with taxes and fees
Ocean Blue & Sand Beach Resort - All Inclusive features a private beach, a full-service spa, and 2 outdoor pools. You can put free parking to good use if you drive. Multilingual staff at the 24-hour front desk can assist with tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this all-inclusive property include a nightclub, 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.
