
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
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,268 reviews)
Jan 18 - Jan 23
5 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Roundtrip • Coach
Price was $2,855, price is now $1,365 per person
$1,365
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025

4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
9/10 Wonderful! (1,398 reviews)
Jan 7 - Jan 12
5 night stay
Boston (BOS) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight  
Price was $2,052, price is now $1,140 per person
$1,140
per person
found 1 day ago
I had a 7 night stay at this resort when I get there I realize my ac wasn’t working as it should and without the ceiling fan the room wouldn’t cold I report this issues they say they will get it fix nxt day I see it was leaking in the closet area I report it again on the third night I called the front desk n I told them I’m really hot here n it’s not working I didn’t want to move because I had a early trip to Anguilla n would be no til later in the night. I wanted a good night sleep so they offer an additional fan then I change my mind n tel her to move me she found 2 room my husband went and check them out I pack all our stuff n ready to move then I got a called saying no to take everything as they only moving me for the night I was upset n I say at this point I wanna sleep when I get bk I will deal with the moving again I asked y would we have to move again she say because the room was in a different part and was a bigger room I said ok. The following day my husband got a call on his wats app n they apologized for the inconvenience and say they will let us stay in the room they move us to ( upgraded stay) apart from tht the front desk staff n everyone was so warm n friendly i would definitely stay again on my nxt visit to st martin
Reviewed on Oct 30, 2025

3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (966 reviews)
Jan 18 - Jan 23
5 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight  
Price was $1,660, price is now $954 per person
$954
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 18 - Jan 23
5 night stay
Boston (BOS) to Philipsburg (SXM)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight  
Price was $1,881, price is now $1,228 per person
$1,228
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
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
$460 nightly
The price is $506 total per night
$506 total
Nov 5 - Nov 6
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 concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
Playas de Bavaro, Higuey, Punta Cana, La Altagracia
131.05 mi from city center
$370 nightly
The price is $474 total per night
$474 total
Dec 3 - Dec 4
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 luggage storage, dry cleaning/laundry, and securing valuables. Other amenities at this all-inclusive property include a children's pool, a gym, and a sauna.
Pool
Breakfast included

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 concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this adults-only property include a gym, a steam room, and free WiFi in public areas.
Pool
Hot Tub
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.








