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 10 - Oct 17
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Price was $2,251, price is now $898 per person
$898
per person
found 1 day ago
Great location and great for families. Huge property though. Pool and beach area were great. Room was large with all the amenities. Small grocery store within walking distance. A lot of restaurants nearby.
Reviewed on Aug 9, 2026
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,484 reviews)
Oct 10 - Oct 17
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Price was $3,216, price is now $1,164 per person
$1,164
per person
found 1 day ago
The property was well kept and a good value. There are many restaurants in the area and it is close to night clubs. I did not enjoy the breakfast buffet served at the hotel. However, overall the food was good.
Reviewed on Aug 8, 2026
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (768 reviews)
Oct 17 - Oct 24
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,834, price is now $1,004 per person
$1,004
per person
found 1 day ago
The overall property was nice. There was mold on the ceiling from water leaking in the unit above. The shower leaks a lot of water onto the floor and the toilet rocks and needs tightened to the floor. The light above the kitchen sink only stays on a few seconds. The room was clean and overall resort was nice.
Reviewed on Aug 6, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,004 reviews)
Oct 10 - Oct 17
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,797, price is now $988 per person
$988
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
5.0-star property
Sonesta Ocean Point All Inclusive, Adults Only Resort
8.8/10 Excellent! (1,003 reviews)
Oct 10 - Oct 17
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $6,348, price is now $3,876 per person
$3,876
per person
found 1 day ago
Everyone was so friendly and accommodating. My husband and I will definitely be returning!
Reviewed on Aug 8, 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 23 - Aug 24
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
$365 nightly
The price is $397 total per night
$397 total
Aug 30 - Aug 31
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
Free Cancellation
Reserve now, pay when you stay
131.05 mi from city center
$278 nightly
The price is $356 total per night
$356 total
Sep 8 - Sep 9
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.
