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! (1,922 reviews)
Oct 12 - Oct 16
4 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,494, price is now $756 per person
$756
per person
found 1 day ago
Great place super clean and affordable
Reviewed on Aug 11, 2026
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,484 reviews)
Nov 1 - Nov 9
8 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sterling Blue • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Air Canada • Non-stop • Coach
Price was $3,355, price is now $1,270 per person
$1,270
per person
found 1 day ago
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,003 reviews)
Nov 1 - Nov 9
8 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sterling Blue • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Air Canada • Non-stop • Coach
Save 100% on your flight
Price was $1,719, price is now $1,030 per person
$1,030
per person
found 1 day ago
This property is nice.. it almost felt deserted as we didn’t see anyone at night. It was very clean, comfortable and we had everything needed. My only complaint was the room needed more light. I’d stay here again .
Reviewed on Aug 8, 2026
4.0-star property
Holland House Beach Hotel
Downtown Philipsburg
9.2/10 Wonderful! (1,006 reviews)
Nov 1 - Nov 9
8 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sterling Blue • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Air Canada • Non-stop • Coach
Save 100% on your flight
Price was $1,874, price is now $1,131 per person
$1,131
per person
found 1 day ago
Very nice hotel, centrally located. The staff were very nice. My only complaint, the bathroom was very nice looking, but not functional.
Reviewed on Aug 10, 2026
4.0-star property
Oyster Bay Beach Resort
Oyster Pond
8.8/10 Excellent! (999 reviews)
Nov 1 - Nov 9
8 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sterling Blue • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Air Canada • Non-stop • Coach
Save 100% on your flight
Price was $1,277, price is now $848 per person
$848
per person
found 1 day ago
My stay was good. The staff is helpful. The food is good. The pool is big and deep. Loved the hot tub. I was able to get a car to rent on the property and the bed was very comfortable. I would definitely return.
Reviewed on Aug 10, 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
$327 nightly
The price is $357 total per night
$357 total
Aug 24 - Aug 25
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.
Pool
Spa
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Free Cancellation
Reserve now, pay when you stay
301.79 mi from city center
$310 nightly
The price is $338 total per night
$338 total
Sep 10 - Sep 11
Total with taxes and fees
Hyatt Regency Grand Reserve Puerto Rico features a golf course, a full-service spa, and 3 outdoor pools. Parking is USD 16.73 per night (USD 27.88 per night for valet parking)—but if you prefer not to drive, catch a ride in the airport shuttle (available 24 hours) for USD 96 per person roundtrip. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this spa resort include a children's pool, a 24-hour gym, and free WiFi in public areas.
Pool
Spa
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Playas de Bavaro Punta Cana La Altagracia
131.05 mi from city center
$266 nightly
The price is $340 total per night
$340 total
Sep 9 - Sep 10
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
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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.
