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
9/10 Wonderful! (1,345 reviews)
Oct 24 - Oct 29
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Price was $1,041, price is now $663 per person
$663
per person
found 1 day ago
I had an excellent time, everything was perfect. Staff were polite and very helpful. 5 star experience.
Reviewed on Jul 31, 2025
4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,241 reviews)
Oct 24 - Oct 29
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Save 100% on your flight
Price was $1,340, price is now $787 per person
$787
per person
found 1 day ago
Had a great time! Room clean and updated. Great staff and location!!
Reviewed on Aug 4, 2025
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (964 reviews)
Nov 28 - Dec 3
5 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,126, price is now $698 per person
$698
per person
found 1 day ago
Overall a great choice to stay
Reviewed on Feb 18, 2025
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (592 reviews)
Nov 28 - Dec 3
5 night stay
Boston (BOS) to Philipsburg (SXM)
Air Canada • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,610, price is now $1,105 per person
$1,105
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
4.0-star property
Oyster Bay Beach Resort
Oyster Pond
8.6/10 Excellent! (932 reviews)
Oct 24 - Oct 29
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
United • Non-stop • Coach
Price was $1,050, price is now $732 per person
$732
per person
found 1 day ago
Beautiful area on St Maarten. Peaceful, serene, quiet, gorgeous views of the ocean, St Barts, and the mountains of the island
Reviewed on Jul 20, 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
$383 nightly
The price is $421 total per night
$421 total
Oct 4 - Oct 5
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 luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
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
$336 nightly
The price is $430 total per night
$430 total
Sep 21 - Sep 22
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 securing valuables, tours or tickets, and luggage storage. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included
Hyatt Vacation Club at Hacienda del Mar, Dorado
301 Hwy 693, Dorado, Vega Alta
Free Cancellation
267.23 mi from city center
$173 nightly
The price is $189 total per night
$189 total
Oct 21 - Oct 22
Total with taxes and fees
Hyatt Vacation Club at Hacienda del Mar, Dorado features an outdoor pool, a children's pool, and a gym. The front desk has multilingual staff that can help with dry cleaning/laundry and securing valuables. Other amenities at this beach resort include free WiFi in public areas, a hot tub, and laundry facilities.
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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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