Kid friendly Holidays in Caribbean Islands 2026

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Price found within the past 48 hours. Click for updated prices.

Bahia Principe Explore Punta Cana - Hyatt Inclusive Collection - All Inclusive

Bávaro

€787

per person

25 Oct - 30 Oct

found 1 day ago

Return flight included

Chicago (ORD) to Punta Cana (PUJ)

7.4/10 Good! (1,698 reviews)

Los cuartos son muy amplios la limpieza muy buena,

Reviewed on 3 Aug 2026

Moon Palace Jamaica – All Inclusive

€1,742

per person

3 Oct - 10 Oct

found 4 hours ago

Return flight included

Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

8.4/10 Very good! (2,085 reviews)

Housekeeper interacts very well and did an awesome job Inroom dining was also very quick Staff over all 10/10 Will definitely be back

Reviewed on 3 Aug 2026

Bahia Principe Explore Legend - Hyatt Inclusive Collection - All Inclusive

Bávaro

€886

per person

25 Oct - 30 Oct

found 1 day ago

Return flight included

Chicago (ORD) to Punta Cana (PUJ)

8.4/10 Very good! (2,438 reviews)

Grand Palladium Jamaica Resort & Spa All Inclusive

€1,404

per person

3 Oct - 10 Oct

found 4 hours ago

Return flight included

Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

8/10 Very good! (1,583 reviews)

This place is the nicest place I ever been to in my life

Reviewed on 3 Aug 2026

Zel Punta Cana, All Suites - All inclusive

Bávaro

€1,001

per person

25 Oct - 30 Oct

found 1 day ago

Return flight included

Chicago (ORD) to Punta Cana (PUJ)

9/10 Wonderful! (891 reviews)

Rooms were well kept and tons of activities that were included which I had never seen at another all inclusive before

Reviewed on 3 Aug 2026

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Price found within the past 48 hours. Click for updated prices.

Zel Punta Cana, All Suites - All inclusive

Bávaro

€1,001

per person

25 Oct - 30 Oct

found 1 day ago

Return flight included

Chicago (ORD) to Punta Cana (PUJ)

9/10 Wonderful! (891 reviews)

Rooms were well kept and tons of activities that were included which I had never seen at another all inclusive before

Reviewed on 3 Aug 2026

Moon Palace Jamaica – All Inclusive

€1,742

per person

3 Oct - 10 Oct

found 4 hours ago

Return flight included

Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

8.4/10 Very good! (2,085 reviews)

Housekeeper interacts very well and did an awesome job Inroom dining was also very quick Staff over all 10/10 Will definitely be back

Reviewed on 3 Aug 2026

Grand Palladium Jamaica Resort & Spa All Inclusive

€1,404

per person

3 Oct - 10 Oct

found 4 hours ago

Return flight included

Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

8/10 Very good! (1,583 reviews)

This place is the nicest place I ever been to in my life

Reviewed on 3 Aug 2026

Don't see what you're looking for?

See all available trips from Chicago to Caribbean Islands

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Barceló Bávaro Palace - All Inclusive

Carretera Bávaro Km. 1 Punta Cana La Altagracia

13 hours drive from Oyster Bay Marina

Stay at this luxury resort in Punta Cana. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the helpful staff in their reviews. ...

8.2/10 Very good! (5,948 reviews)

Families like: Outdoor pools, waterslide, children's club, playground

Travellers say...

"Maintenance is very poor the outlet in my bedroom was damaged ,buffet food was very bad no many options very bad quality"

Reviewed on 3 Aug 2026

Majestic Colonial Punta Cana - All Inclusive

Carretera El Macao Punta Cana La Altagracia

13 hours drive from Oyster Bay Marina

Stay at this beach resort in Punta Cana. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. Popular ...

Dreams Rose Hall Resort & Spa - All Inclusive

Rose Hall Montego Bay Saint James

33 hours drive from Oyster Bay Marina

Stay at this luxury resort in Montego Bay. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...

8.4/10 Very good! (1,578 reviews)

Families like: Outdoor pools, free water park access, children's club, playground

Travellers say...

"All was good"

Reviewed on 15 Jan 2026

See all 88,367 properties in Caribbean Islands

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.