Caribbean Islands Vacation Packages
Book a Stay + Flight or Car to save on your trip
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 17 - Oct 24
7 night stay
Albany (ALB) to Philipsburg (SXM)
American Airlines • Roundtrip • Coach
Price was $2,353, price is now $1,005 per person
$1,005
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 12 - Oct 19
7 night stay
Albany (ALB) to Philipsburg (SXM)
Southwest Airlines • Non-stop • Coach
Philipsburg (SXM) to Albany (ALB)
American Airlines • Non-stop • Coach
Price was $3,411, price is now $1,503 per person
$1,503
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
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,004 reviews)
Oct 12 - Oct 19
7 night stay
Albany (ALB) to Philipsburg (SXM)
Southwest Airlines • Non-stop • Coach
Philipsburg (SXM) to Albany (ALB)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,972, price is now $1,281 per person
$1,281
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 12 - Oct 19
7 night stay
Albany (ALB) to Philipsburg (SXM)
Southwest Airlines • Non-stop • Coach
Philipsburg (SXM) to Albany (ALB)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $6,473, price is now $4,532 per person
$4,532
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
4.0-star property
The Forest
10/10 Exceptional! (26 reviews)
Oct 14 - Oct 21
7 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sterling Blue • Non-stop • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,722, price is now $1,219 per person
$1,219
per person
found 1 day ago
What a wonderful stay!! The staff was exceptional and accommodating the entire trip. The rooms were clean and very beautiful, not to mention the landscaping and the ease of getting to and from. I will most certainly be back!! Thank you!!!
Reviewed on May 11, 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
The price is $357 total per night
$357 total
per night
Aug 23 - Aug 24
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
The price is $397 total per night
$397 total
per night
Aug 30 - Aug 31
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
The price is $356 total per night
$356 total
per night
Sep 9 - Sep 10
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
Don't see what you're looking for?
See all available properties in Caribbean Islands
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.
