Caribbean Islands Vacation Packages
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4.0-star property
The Villas at Simpson Bay Resort
9.2/10 Wonderful! (1,154 reviews)
Jul 27 - Jul 30
3 night stay
Boston (BOS) to Philipsburg (SXM)
United • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Everything you need right at the resort though there are several other restaurants within walking distance. The staff are Coco Beach bar are the best!!
Reviewed on Apr 12, 2025
3.5-star property
Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
9.2/10 Wonderful! (872 reviews)
Jun 4 - Jun 11
7 night stay
Austin (AUS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
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per person
found 4 hours ago
Overall a great choice to stay
Reviewed on Feb 18, 2025
4.0-star property
Simpson Bay Resort, Marina & Spa
Pelican Key
8.8/10 Excellent! (1,048 reviews)
Jun 9 - Jun 13
4 night stay
Austin (AUS) to Philipsburg (SXM)
Delta • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
Very nice property. Our only complaint it that it appears that they add a bleach smell to the air of both the condo unit and the main lobby that was bothersome. Everything else was excellent, including service from bellmen and others.
Reviewed on Mar 22, 2025
4.0-star property
La Playa Orient Bay
9.4/10 Exceptional! (482 reviews)
Jun 4 - Jun 11
7 night stay
Austin (AUS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 4 hours 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
Divi Little Bay Beach Resort
8.4/10 Very Good! (1,003 reviews)
Jul 6 - Jul 10
4 night stay
Austin (AUS) to Philipsburg (SXM)
American Airlines • Non-stop roundtrip • Coach
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per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025
Top rated hotels for your Caribbean Islands vacation package
Serenade Punta Cana Beach & Spa Resort - All Inclusive
Carretera Cabeza de Toro, Punta Cana, La Altagracia
Free Cancellation
Reserve now, pay when you stay
134.26 mi from city center
The price is $287 per night
$287
includes taxes & fees
$243 per night
May 15 - May 16
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.
On private beach
Pool
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 $489 per night
$489
includes taxes & fees
$445 per night
Jun 1 - Jun 2
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.
Pool
Spa
The Condado Plaza Hotel
999 Ashford Avenue, San Juan
Free Cancellation
Reserve now, pay when you stay
282.81 mi from city center
The price is $261 per night
$261
includes taxes & fees
$239 per night
Jun 1 - Jun 2
At The Condado Plaza Hotel, guests enjoy 2 outdoor pools, a children's pool, and a 24-hour gym. Valet parking is offered for USD 31.22 per night. The 24-hour front desk has multilingual staff ready to assist with securing valuables, concierge services, and access to locker space. Other amenities at this beach resort include conference space, express check-out, and free newspapers.
Pool
Restaurant
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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.
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