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
La Playa Orient Bay
9.4/10 Exceptional! (668 reviews)
May 25 - May 29
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,137, price is now $778 per person
$778
per person
found 1 day ago
All the folks working at this property were great. The resort was nice but not pretentious.
Reviewed on Nov 18, 2024
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,387 reviews)
Jun 14 - Jun 20
6 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $2,505, price is now $1,302 per person
$1,302
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! (1,629 reviews)
Jun 14 - Jun 20
6 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop • Coach
Philipsburg (SXM) to Boston (BOS)
JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $2,267, price is now $1,199 per person
$1,199
per person
found 1 day ago
Nice beach, nice staff. Only gripe is charging to use the gym - come on, that’s cheap
Reviewed on Mar 7, 2026
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (1,007 reviews)
Apr 21 - Apr 25
4 night stay
Boston (BOS) to Philipsburg (SXM)
American Airlines • Roundtrip • Coach
Price was $1,618, price is now $1,109 per person
$1,109
per person
found 1 day ago
The room was spacious, clean and had adequate storage. The kitchenette was properly outfitted and they gave us a few complimentary drinks, The place was very quiet and private.
Reviewed on Nov 26, 2025
5.0-star property
Sonesta Ocean Point All Inclusive, Adults Only Resort
8.6/10 Excellent! (1,006 reviews)
May 28 - May 31
3 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 $3,148, price is now $2,240 per person
$2,240
per person
found 1 day ago
Can’t think of anything we didn’t like. Food and accommodations were excellent.
Reviewed on Jul 20, 2025
Top rated hotels for your Caribbean Islands vacation package
Hotel Riu Montego Bay - Adults Only - All Inclusive
Mahoe Bay, Ironshore Montego Bay Saint James
489.91 mi from city center
$374 nightly
The price is $415 total per night
$415 total
Apr 21 - Apr 22
Total with taxes and fees
Hotel Riu Montego Bay - Adults Only - All Inclusive features a full-service spa, 5 outdoor pools, and a free water park. There's free parking and limo/town car service. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this adults-only property include a nightclub, 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.
Serenade Punta Cana Beach & Spa Resort - All Inclusive
Carretera Cabeza de Toro Punta Cana La Altagracia
134.26 mi from city center
$447 nightly
The price is $572 total per night
$572 total
Mar 29 - Mar 30
Total with taxes and fees
Serenade Punta Cana Beach & Spa Resort - All Inclusive features a private beach, a full-service spa, and 3 outdoor pools. You can put free parking to good use if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this all-inclusive property include a free water park, a children's pool, and a gym.
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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.
