Caribbean Islands Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (2,129 reviews)
Jan 8 - Jan 12
4 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Price was $2,182, price is now $1,062 per person
$1,062
per person
found 19 hours ago
Love the property everything was clean to a tea. We had staff cleaning every day up making sure everything was at its Best, best birthday trip ever for my husband. Thank you for making it extra special.❤️❤️❤️❤️❤️👌👌👌💕💕💕💕 recommend 10 out of 10 pool was everywhere staff was friendly casino was right. Their pool bar was right there.
Reviewed on Oct 31, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,001 reviews)
Dec 9 - Dec 16
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Price was $2,379, price is now $1,075 per person
$1,075
per person
found 1 day ago
My cousin and I had a great overnight stay @ your hotel. The staff was very helpful. Paul was great !!!
Reviewed on Oct 24, 2026
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,584 reviews)
Dec 9 - Dec 16
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Price was $2,423, price is now $1,146 per person
$1,146
per person
found 1 day ago
4.5-star property
Panorama Residences at Monte Vista
Point Blanche
9.6/10 Exceptional! (104 reviews)
Dec 9 - Dec 16
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Price was $2,740, price is now $1,569 per person
$1,569
per person
found 1 day ago
Super clean, beautiful location. Friendly staff. Safe place. Will book again
Reviewed on Oct 24, 2026
4.0-star property
The Morgan Resort Spa Village
9/10 Wonderful! (2,427 reviews)
Dec 9 - Dec 16
7 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Delta • Non-stop • Coach
Price was $2,635, price is now $1,512 per person
$1,512
per person
found 1 day ago
The entire stay was great. Easy and quick pick up from the airport. Welcome drink upon arrival. They were able to get all of our rooms close together (girl’s trip). The restaurant was conveniently located. Free prosecco on Thursdays. The breakfast was good, fast and tasty. The room was well decorated and clean. Any requests were met quickly and efficiently. The grounds were beautiful and walkable to nearby Maho beach and shopping. No critiques.
Reviewed on Oct 31, 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
$407 nightly
The price is $445 total per night
$445 total
Nov 1 - Nov 2
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 dry cleaning/laundry. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa
Wyndham Alltra Punta Cana All-Inclusive Resort
Playas Uvero Alto Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
120.96 mi from city center
$280 nightly
The price is $280 total per night
$280 total
Nov 30 - Dec 1
Total with taxes and fees
Guests of Wyndham Alltra Punta Cana All-Inclusive Resort have access to 2 outdoor pools, a free water park, and a lazy river. If you plan to drive, free valet parking is available. The 24-hour front desk has staff always at the ready. Other amenities at this all-inclusive resort include a children's pool, a gym, and free WiFi in public areas.
Pool
Breakfast included
Hotel Riu Montego Bay - Adults Only - All Inclusive
Mahoe Bay, Ironshore Montego Bay Saint James
489.91 mi from city center
Hotel Riu Montego Bay - Adults Only - All Inclusive features a full-service spa, 5 outdoor pools, and a free water park. Free parking is included with your stay. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and tours or tickets. Additional amenities include a nightclub, a gym, and a sauna.
Pool
Hot Tub
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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.
