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Family vacations

Experience the family vacation of a lifetime! Choose from the widest selection of Trip Advisor’s® top-rated, all inclusive family resorts in the Caribbean, Mexico and Central America. These top-rated resorts offer free access to the largest water parks in the Caribbean, resorts that accommodate families of five or more and properties where Kids Stay, Play and Eat FREE!

Family vacations aren’t just for the little ones! Plan your extended family getaway in paradise and enjoy added perks when you travel with ten or more adults. Take advantage of exclusive perks including reduced deposits, private transfers and more. Click here to learn more!

Search for your vacation from a selection of:

Top-rated family resorts
Resorts that our customers know and love

Smile Resorts™
Where Kids Stay, Play and Eat FREE

SplashWorld Resorts
Includes free access to the largest waterparks under the sun

Larger rooms
Accommodating 5 or more

New taxes and fees now included in pricing!
Varadero, Cuba
Save up to 25%!
Winnipeg to Varadero
Tue, November 5, 2019 7 days All inclusive
Reg. $1,895
From $1,425 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 16%!
Winnipeg to Cayo Coco
Sat, January 18, 2020 7 days All inclusive
Reg. $1,835
From $1,535 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 8%!
Winnipeg to Mazatlán
Fri, December 13, 2019 7 days All inclusive
Reg. $1,745
From $1,605 taxes and fees incl.
Prefer another date?
Save up to 12%!
Winnipeg to Holguin
Fri, December 13, 2019 7 days All inclusive
Reg. $1,815
From $1,595 taxes and fees incl.
Prefer another date?
Save up to 17%!
Winnipeg to Varadero
Tue, November 5, 2019 7 days All inclusive
Reg. $1,995
From $1,655 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 10%!
Winnipeg to Riviera Nayarit
Fri, November 29, 2019 7 days All inclusive
Reg. $1,915
From $1,715 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 25%!
Winnipeg to Varadero
Tue, November 5, 2019 7 days All inclusive
Reg. $1,385
From $1,045 taxes and fees incl.
Prefer another date?
Save up to 29%!
Winnipeg to Varadero
Tue, November 5, 2019 7 days All inclusive
Reg. $1,535
From $1,095 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 11%!
Winnipeg to Punta Cana
Wed, November 6, 2019 7 days All inclusive
Reg. $2,085
From $1,865 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 15%!
Winnipeg to Riviera Maya
Mon, December 2, 2019 7 days All inclusive
Reg. $2,125
From $1,815 taxes and fees incl.
Prefer another date?
Save up to 15%!
Winnipeg to Jamaica
Mon, December 16, 2019 7 days All inclusive
Reg. $2,275
From $1,945 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 25%!
Winnipeg to Varadero
Tue, November 5, 2019 7 days All inclusive
Reg. $1,365
From $1,025 taxes and fees incl.
Prefer another date?
Save up to 29%!
Winnipeg to Varadero
Tue, November 5, 2019 7 days All inclusive
Reg. $1,535
From $1,095 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 16%!
Winnipeg to Havana
Tue, November 5, 2019 7 days Continental Plan
Reg. $1,385
From $1,165 taxes and fees incl.
Prefer another date?

The prices shown reflect rates of the day and are subject to change at any time without prior notice. To confirm availability and final pricing you MUST proceed to Step 3. The price shown at Step 3 constitutes the final guaranteed price and prevails over any other price.

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