Caribbean Islands Vacation Packages
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4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,442 reviews)
Sep 5 - Sep 9
4 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
American Airlines • Coach
Price was $1,554, price is now $798 per person
$798
per person
found 1 day ago
The room was clean but there was a hole in the ceiling above the bathroom sink. I enjoy my stay and was very comfortable overall. I
Reviewed on Jul 2, 2026
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,837 reviews)
Aug 8 - Aug 15
7 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to Boston (BOS)
Air Canada • Coach
Save 100% on your flight
Price was $2,511, price is now $1,237 per person
$1,237
per person
found 1 day ago
The beach was amazing.My room location on the marina was lovely and the workers and manger for the check were n was great
Reviewed on Jul 1, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,003 reviews)
Aug 8 - Aug 15
7 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to Boston (BOS)
Air Canada • Coach
Price was $1,564, price is now $994 per person
$994
per person
found 1 day ago
Quiet, peaceful, serene stay. Everything is 5 out of 5!
Reviewed on Jun 25, 2026
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (736 reviews)
Aug 8 - Aug 15
7 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to Boston (BOS)
Air Canada • Coach
Save 100% on your flight
Price was $2,009, price is now $1,293 per person
$1,293
per person
found 1 day ago
We loved our stay at La Playa! From the moment we arrived the staff was so friendly and helpful with anything we needed. The property itself and the rooms were extremely clean and well kept. The small villa style apartments gave the place a really cool and quaint feel. The beach bar and beach area were also incredible. Tristan at the beach was also very helpful with chairs and service throughout the day. There was some sargassum during our stay but the staff cleaned the beach each morning and kept everything as nice as they possibly could have. 10/10 recommend staying here- we already can’t wait to go back!
Reviewed on Jul 2, 2026
4.0-star property
The Morgan Resort Spa Village
9/10 Wonderful! (2,255 reviews)
Aug 8 - Aug 15
7 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Coach
Philipsburg (SXM) to Boston (BOS)
Air Canada • Coach
Save 100% on your flight
Price was $2,347, price is now $1,576 per person
$1,576
per person
found 1 day ago
Love the distance to airport and free shuttle. Staff was great especially Perla! Drinks on property a bit expensive but thats expected. Pools were amazing.
Reviewed on Jul 2, 2026
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
$424 nightly
The price is $465 total per night
$465 total
Jul 28 - Jul 29
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 concierge services, luggage storage, and securing valuables. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa
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
$339 nightly
The price is $339 total per night
$339 total
Jul 7 - Jul 8
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 concierge services, 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
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, luggage storage, and tours or tickets. Other amenities at this all-inclusive property include a free water park, a nightclub, and karaoke.
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.
