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! (1,398 reviews)
Jan 6 - Jan 11
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,778, price is now $900 per person
$900
per person
found 1 day ago
Stay at Simpson Bay studio suite turned out to actually be in steep, uphill Royal resort bldg with no view of water, not close to beach and room itself faced parking lot. Room was clean, although the water faucets for some reason leaked, and the most annoying part of stay was that you needed to walk to a “towel booth” near the security booth to get clean towels, rather than having them available by pool. Parking was luckily available, and renting a car would be needed for this hotel, as well as for ease in getting around.
Reviewed on Oct 18, 2025
4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,268 reviews)
Jan 4 - Jan 9
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
United • Coach
Philipsburg (SXM) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Coach
Price was $2,677, price is now $1,127 per person
$1,127
per person
found 16 hours ago
The resort grounds are beautiful and immaculately maintained! All the staff were friendly and helpful. The room was very clean and had plenty of amenities. A very nice stay for the money!
Reviewed on Oct 8, 2025
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (966 reviews)
Jan 1 - Jan 9
8 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,516, price is now $1,446 per person
$1,446
per person
found 1 day ago
Overall a great choice to stay
Reviewed on Feb 18, 2025
4.0-star property
Holland House Beach Hotel
Downtown Philipsburg
9.2/10 Wonderful! (1,000 reviews)
Jan 6 - Jan 11
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,425, price is now $1,430 per person
$1,430
per person
found 1 day ago
The staff are amazing and it is super convenient to stores.
Breakfast was great!
Reviewed on Sep 5, 2025
4.0-star property
Oceans at Divi Little Bay
8.4/10 Very Good! (262 reviews)
Jan 6 - Jan 11
5 night stay
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,317, price is now $1,470 per person
$1,470
per person
found 1 day ago
Great property for families
Reviewed on Jul 31, 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
The price is $461 total per night
$461 total
per night
Oct 29 - Oct 30
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 dry cleaning/laundry, tours or tickets, and securing valuables. 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
The price is $430 total per night
$430 total
per night
Oct 21 - Oct 22
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, dry cleaning/laundry, and luggage storage. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Hotel Riu Republica - Adults only - All Inclusive
Playa Arena Gorda, Punta Cana
126.6 mi from city center
Hotel Riu Republica - Adults only - All Inclusive features a free water park, a nightclub, and an outdoor pool. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this adults-only property include a gym, a steam room, and free WiFi in public areas.
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.
