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
Simpson Bay Resort, Marina & Spa
Pelican Key
8.8/10 Excellent! (1,048 reviews)
May 27 - May 31
4 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Very nice property. Our only complaint it that it appears that they add a bleach smell to the air of both the condo unit and the main lobby that was bothersome. Everything else was excellent, including service from bellmen and others.
Reviewed on Mar 22, 2025
4.0-star property
Divi Little Bay Beach Resort
8.4/10 Very Good! (1,003 reviews)
Jun 21 - Jun 26
5 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025
4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,154 reviews)
Jul 10 - Jul 13
3 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Everything you need right at the resort though there are several other restaurants within walking distance. The staff are Coco Beach bar are the best!!
Reviewed on Apr 12, 2025
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (482 reviews)
May 23 - May 26
3 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop roundtrip • Coach
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
Serenade Punta Cana Beach & Spa Resort - All Inclusive
Carretera Cabeza de Toro, Punta Cana, La Altagracia
134.26 mi from city center
The price is $346 per night
$346
includes taxes & fees
$294 per night
May 15 - May 16
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, tours or tickets, and luggage storage. Other amenities at this all-inclusive property include a free water park, a children's pool, and a gym.
On private beach
Pool
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
The price is $475 per night
$475
includes taxes & fees
$403 per night
Apr 28 - Apr 29
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, luggage storage, and tours or tickets. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included
Ocean Blue & Sand Beach Resort - All Inclusive
Car. Arena Gorda, Playa Bavaro, Punta Cana, La Altagracia
128.45 mi from city center
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 luggage storage, concierge services, 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.
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