Caribbean Vacation Packages

They vary in landscape, size, and vibe, but each Caribbean island has a reason (or ten) for being on your bucket list. Discover your all-inclusive Caribbean vacation paradise.

Caribbean Vacation Package Deals

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142 Hotels

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Bahia Principe Grand Punta Cana - All Inclusive

4.5 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Dominican Republic, Punta Cana

Best Priced Departure Dates

2025: Nov 16, Nov 19, Dec 3, Dec 10, Dec 13, Dec 19

3 Nights Hotel From

$309 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Bahia Principe Luxury Runaway Bay Adults Only - All Inclusive

4.5 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Jamaica, Montego Bay

Best Priced Departure Dates

2025: Nov 19, Nov 21, Nov 22, Nov 25, Nov 26, Dec 3, Dec 12, Dec 14, Dec 16, Dec 17

4 Nights Hotel From

$726 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Catalonia Montego Bay - AIl Inclusive

3 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Jamaica, Montego Bay

Best Priced Departure Dates

2025: Nov 19 - Nov 22, Nov 24 - Nov 26, Nov 28, Nov 29, Dec 1, Dec 3 - Dec 5, Dec 8, Dec 9, Dec 12, Dec 14 - Dec 17, Dec 19, Dec 20

4 Nights Hotel From

$413 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Couples Negril - All Inclusive

4.5 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Jamaica, Montego Bay

Best Priced Departure Dates

2025: Dec 20, Dec 21

4 Nights Hotel From

$1,210 per person Includes Taxes + Fees
Dreams Cap Cana - All Inclusive

5 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Dominican Republic, Punta Cana

Best Priced Departure Dates

2025: Nov 1, Nov 3, Nov 9, Nov 16 - Nov 19, Nov 21 - Nov 27

4 Nights Hotel From

$734 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Grand Palladium Jamaica Resort & Spa - All Inclusive

4 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Jamaica, Montego Bay

Best Priced Departure Dates

Dec 8, 2025

4 Nights Hotel From

$765 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews
- Accessible Resort
JOIA Rose Hall by Iberostar (Formerly Iberostar Grand Rose Hall) - All Inclusive

5 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Jamaica, Montego Bay

Best Priced Departure Dates

Dec 14, 2025

4 Nights Hotel From

$1,055 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Live Aqua Beach Resort Punta Cana - All Inclusive

5 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Dominican Republic, Punta Cana

Best Priced Departure Dates

2025: Nov 3, Nov 10

3 Nights Hotel From

$639 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Ocean Blue & Sand - All Inclusive

4 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Dominican Republic, Punta Cana

Best Priced Departure Dates

Oct 30, 2025

3 Nights Hotel From

$328 per person Includes Taxes + Fees
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Ocean Coral Spring - All Inclusive

4.5 star hotel

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

All-Inclusive

Jamaica, Montego Bay

Best Priced Departure Dates

2025: Nov 24 - Nov 26, Nov 29

4 Nights Hotel From

$768 per person Includes Taxes + Fees

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Showing 1-10 of 142

Caribbean Vacation Packages

Ready to plan your Caribbean vacation? Whether you're looking for an island adventure or a secluded retreat on the surrounding mainland, the region has something for everyone, from solo travelers to friends to couples and families. Best of all, arranging an all-inclusive trip to the Caribbean islands can help make the experience more fun and more affordable for everyone. Resorts, meals, entertainment, and even excursions are all covered under one price. There are no surprises and no worries about what the final bill will be!

Featured Caribbean Vacations

TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Kingston

Secrets St. James Montego Bay - All Inclusive
Book Now
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

Punta Cana

Riu Palace Punta Cana - All Inclusive
Book Now
TripAdvisor Traveler Rating

based on TripAdvisor Reviews

La Romana via Santo Domingo

Iberostar Selection Hacienda Dominicus - All Inclusive
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The Islands of the Caribbean

Antigua

The perfect blend of beaches, restaurants, adventure, and old world charm. Rendezvous Bay offers one of the best beaches in Antigua.

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Aruba

This little desert island packs a lot of personality for you and your family. We dare you to run out of things to do.

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Bahamas

In this lively area of the Caribbean, every day is a trip to the beach with plenty of attractions and nights on the town.

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Barbados

Barbados hosts both British and Caribbean traditions, ranging from afternoon tea and cricket, to scuba and snorkeling on Dottins Reef, and a round of golf on designer oceanside courses. Soak up sun and history.

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Bermuda

With 181 islands to explore and a wide variety of attractions and activities, your options are almost limitless. Bermuda is famous for pink-sand beaches like Elbow Beach and Horseshoe Bay.

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Grand Cayman

If you love the ocean, the beach, good restaurants, and local attractions, then you’ll adore this island paradise. Stingray City is perfect for family friendly fun.

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Jamaica

Reggae music, steel drums, amazing restaurants, beautiful beaches, and local festivals. Who wouldn’t want to vacation in the birthplace of the “no worries” mentality?

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Puerto Rico

European charm, Latin flare, stunning attractions, and tropical landscapes - Puerto Rico combines the best of everything.

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Punta Cana

Leave your wallet in your room. The luxury of Punta Cana in the Dominican Republic is all-inclusive.

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St. Kitts

With so many things to do such as hiking, rock climbing, diving, relaxing on the beach, and enjoying local restaurants, you are sure to discover a unique perspective on culture, nature, and your vacation.

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St. Lucia

Highlighted by the Piton Mountains and home to volcanic beaches, St. Lucia is paradise. Mother Nature made this twenty-seven-mile Caribbean island along the Atlantic ocean her masterpiece.

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St. Maarten (St. Martin)

This tropical hotspot is bursting with French and Dutch culture, attractions, amazing local restaurants, and pristine beaches along the ocean.

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Turks & Caicos

This laid-back string of islands is just a hop, skip, and a jump from the U.S. mainland.

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U.S. Virgin Islands

In St. Croix, St. John, and St. Thomas, you will find all the shopping, beaching, snorkeling, dining, and relaxing your family is craving – with all the ease of domestic travel.

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