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
Simpson Bay Resort, Marina & Spa
Pelican Key
8.8/10 Excellent! (1,653 reviews)
May 31 - Jun 2
2 night stay
Atlanta (ATL) to Philipsburg (SXM)
Spirit Airlines • Non-stop • Coach
Philipsburg (SXM) to Atlanta (ATL)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,196, price is now $668 per person
$668
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
4.0-star property
The Villas at Simpson Bay Resort
Pelican Key
9.2/10 Wonderful! (1,386 reviews)
May 24 - May 28
4 night stay
Atlanta (ATL) to Philipsburg (SXM)
Delta • Coach
Philipsburg (SXM) to Atlanta (ATL)
Spirit Airlines • Coach
Save 100% on your flight
Price was $2,214, price is now $1,178 per person
$1,178
per person
found 1 day ago
Balcony was a beautiful view
Reviewed on Oct 29, 2025
4.0-star property
Divi Little Bay Beach Resort
8.2/10 Very Good! (1,012 reviews)
May 30 - Jun 5
6 night stay
Atlanta (ATL) to Philipsburg (SXM)
Delta • Coach
Philipsburg (SXM) to Atlanta (ATL)
JetBlue Airways • Coach
Save 100% on your flight
Price was $2,671, price is now $1,718 per person
$1,718
per person
found 1 day ago
Nice grounds, well kept and maintained. Beautiful property.
Reviewed on Apr 1, 2025
4.0-star property
Oceans at Divi Little Bay
8.2/10 Very Good! (371 reviews)
May 30 - Jun 5
6 night stay
Atlanta (ATL) to Philipsburg (SXM)
Delta • Coach
Philipsburg (SXM) to Atlanta (ATL)
JetBlue Airways • Coach
Save 100% on your flight
Price was $2,786, price is now $1,855 per person
$1,855
per person
found 1 day ago
Front staff was not courteous or helpful. There was no real explanation of what was included in all inclusive. We paid $200 extra per person to upgrade to premium, and we were not given premium when we got to the Divi. Certain way staff were excellent and others were not overly friendly and did not make eye contact for service very often. There was not a lot of excursions available from the Divi
Reviewed on Feb 18, 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
$424 nightly
The price is $465 total per night
$465 total
May 10 - May 11
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, securing valuables, and dry cleaning/laundry. Other amenities at this beach resort include a casino, a free water park, and a nightclub.
Pool
Spa
Wyndham Alltra Punta Cana All-Inclusive Resort
Playas Uvero Alto Punta Cana La Altagracia
120.96 mi from city center
$281 nightly
The price is $281 total per night
$281 total
May 3 - May 4
Total with taxes and fees
Guests of Wyndham Alltra Punta Cana All-Inclusive Resort have access to 2 outdoor pools, a free water park, and a lazy river. If you plan to drive, free valet parking is available. The 24-hour front desk has staff always at the ready. Other amenities at this all-inclusive resort include a children's pool, a gym, and free WiFi in public areas.
Pool
Breakfast included
Princess Grand Jamaica Resort - All Inclusive
Industry Cove Green Island Hanover
515.39 mi from city center
$455 nightly
The price is $455 total per night
$455 total
Apr 23 - Apr 24
Total with taxes and fees
Princess Grand Jamaica Resort - All Inclusive features a full-service spa, 4 outdoor pools, and a free water park. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with luggage storage and concierge services. Other amenities at this all-inclusive resort include karaoke, a children's pool, and free WiFi in public areas.
Pool
Breakfast included
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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.
