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A beach with clear turquoise water, white sand, and palm trees.

Caribbean Islands Vacations from $531

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Caribbean Islands

A beach lined with palm trees and beach chairs under a clear blue sky.
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Punta Cana

Punta Cana

The Latest Caribbean Islands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • On the beach, free beach shuttle
    Sep 13 - Sep 17

    Palm Green Vacations Whitesands + Flight

    Bávaro
    4 nights
    3.5 star property
    5.4/10 - (3 reviews)
    "I like this property. I had a problem with the lady renting me the apartment. It was a big property and I tried to get clarification but she was very un accommodating and rude. On day of check out I tried to ask why I was moved last minute as soon as I arrived to the country they changed my reservation and only told me once I arrived to property. The place was very beautiful but I was disappointed with the lady I communicated with. She was unprofessional and did not want to help at all "
    Reviewed April 1, 2022
    Roundtrip • New York (EWR) - Punta Cana (PUJ)
    EWR - PUJ • 1 stop PUJ - EWR • Nonstop
    $2,604
    $531
    per traveler
    found 1 day ago
    Palm Green Vacations Whitesands
  • Exterior
    Sep 1 - Sep 6

    Silver Creek Resort + Flight

    Runaway Bay
    5 nights
    3.5 star property
    7.0/10 - Good (51 reviews)
    Roundtrip • New York (JFK) - Montego Bay (MBJ)
    JFK - MBJ • Nonstop MBJ - JFK • 1 stop
    $2,557
    $682
    per traveler
    found 2 days ago
    Silver Creek Resort
  • 3 bars/lounges, swim-up bar, poolside bar, beach bar
    Sep 16 - Sep 20

    Sunset at the Palms Resort - Adults Only - All Inclusive + Flight

    Negril
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,003 reviews)
    "The resort is nice but not one of the nicest we have stayed in. There isn't a whole lot to do so it is more the a person or couple who just want to relax. The beach is also not one of the nicest compared to other resorts down the beach from this resort but they do offer huts which the others don't for sun protection. Water was clean and beautiful."
    Reviewed July 24, 2026
    Roundtrip • New York (EWR) - Montego Bay (MBJ)
    EWR - MBJ • Nonstop MBJ - EWR • 1 stop
    $2,819
    $1,139
    per traveler
    found 2 days ago
    Sunset at the Palms Resort - Adults Only - All Inclusive
  • Front of property
    Oct 11 - Oct 16

    The Villas at Simpson Bay Resort + Flight

    Pelican Key
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,483 reviews)
    "Its in a good location, you can actually walk to restaurants and other beaches."
    Reviewed July 25, 2026
    Roundtrip • New York (EWR) - Saint Martin (SXM)
    EWR - SXM • 1 stop SXM - EWR • 1 stop
    $2,279
    $939
    per traveler
    found 1 day ago
    The Villas at Simpson Bay Resort
  • Boating
    Oct 1 - Oct 6

    Coral Costa Caribe Beach Resort - All Inclusive + Flight

    Villas Del Mar
    5 nights
    4.0 star property
    8.0/10 - Very Good (2,610 reviews)
    "El area de la comida más limpieza. Y mejor atención"
    Reviewed July 25, 2026
    Roundtrip • New York (EWR) - Santo Domingo (SDQ)
    EWR - SDQ • Nonstop SDQ - EWR • Nonstop
    $1,564
    $684
    per traveler
    found 1 day ago
    Coral Costa Caribe Beach Resort - All Inclusive

Discover the most popular places to visit in Caribbean Islands

An old church with a tiled roof, stone walls, and two bell towers.

Altos de Chavon Village

A replica 16th-century Mediterranean village perched on a rocky outcrop above the River Chavón.

Caribbean Islands Hotel Deals

Presidential Suite, 1 King Bed | Minibar, blackout drapes, iron/ironing board, WiFi (free)

Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG
4.5 star property
719.8 mi from Caribbean Islands
9.8 out of 10, Exceptional, (774 reviews)
"We loved Hotel Indigo Cayman Island. Staff are awesome they’re all very friendly. We enjoyed the food in Catalina, very attentive servers. Nice pool but we spent more time at the beach it’s a 4 minute walk at Bonny Moon beach club with free lounge chairs with umbrellas and towels. Hotel has beautiful well maintained grounds. We would definitely go back! Thank you Hotel Indigo your amazing staff made our stay a very pleasant and more enjoyable!"
$267 nightly
The price is $299
Aug 18 - Aug 19
Total with taxes and fees
Hotel Indigo Grand Cayman by IHG
Lowest 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.
See all properties in Caribbean Islands

Book with confidence

Things to do in Caribbean Islands

The Caribbean Islands offer a perfect blend of beach relaxation and cultural exploration. Visitors can enjoy a variety of activities, including underwater sports like scuba diving with provided gear, and adventure activities that include exploring pirate coves. Golf enthusiasts will find excellent courses, while the surrounding recreational areas provide ample opportunities for outdoor fun. A trip to the Caribbean promises unforgettable experiences for every type of traveler.

Best time to go to Caribbean Islands

The best time to visit Caribbean Islands depends on your weather preferences. The hottest average temperature around Caribbean Islands is in September, when weather is mostly sunny and rainfall is light rain. The coolest average temperature around Caribbean Islands is in November when weather is mostly sunny and rainfall is light rain.

Tips to save on your trip to Caribbean Islands

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.