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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 32%!
Windsor to Varadero
Thu, January 9, 2020 7 days All inclusive
Reg. $1,665
From $1,135 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 26%!
Windsor to Varadero
Thu, January 9, 2020 7 days All inclusive
Reg. $1,745
From $1,295 taxes and fees incl.
Prefer another date?
Save up to 27%!
Windsor to Riviera Maya
Mon, January 13, 2020 7 days All inclusive
Reg. $2,035
From $1,495 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 13%!
Windsor to Riviera Maya
Mon, January 13, 2020 7 days All inclusive
Reg. $1,925
From $1,675 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 17%!
Windsor to Cancun
Mon, January 13, 2020 7 days All inclusive
Reg. $2,055
From $1,705 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 22%!
Windsor to Cancun
Mon, January 13, 2020 7 days All inclusive
Reg. $2,195
From $1,705 taxes and fees incl.
Prefer another date?
Save up to 23%!
Windsor to Varadero
Thu, January 9, 2020 7 days All inclusive
Reg. $2,225
From $1,705 taxes and fees incl.
Prefer another date?
Save up to 20%!
Windsor to Riviera Maya
Mon, January 13, 2020 7 days All inclusive
Reg. $2,155
From $1,715 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 28%!
Windsor to Riviera Maya
Mon, January 13, 2020 7 days All inclusive
Reg. $2,455
From $1,765 taxes and fees incl.
Prefer another date?
Save up to 48%!
Windsor to Cancun
Mon, December 16, 2019 7 days All inclusive
Reg. $2,015
From $1,055 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $1,795
From $1,095 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 37%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $1,955
From $1,225 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 37%!
Windsor to Cancun
Mon, December 16, 2019 7 days All inclusive
Reg. $2,005
From $1,255 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $2,125
From $1,295 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $2,115
From $1,295 taxes and fees incl.
Prefer another date?
Save up to 50%!
Windsor to Cancun
Mon, December 16, 2019 7 days All inclusive
Reg. $2,625
From $1,315 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 35%!
Windsor to Cancun
Mon, December 16, 2019 7 days All inclusive
Reg. $2,035
From $1,325 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 36%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $2,055
From $1,325 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 25%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $1,775
From $1,335 taxes and fees incl.
Prefer another date?
Save up to 38%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $2,255
From $1,395 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 34%!
Windsor to Cancun
Mon, December 16, 2019 7 days All inclusive
Reg. $2,235
From $1,475 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 35%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $2,385
From $1,545 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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