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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 35%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,805
From $1,165 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 13%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,625
From $1,415 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 21%!
Windsor to Riviera Maya
Mon, January 21, 2019 7 days All inclusive
Reg. $2,015
From $1,585 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 21%!
Windsor to Riviera Maya
Mon, January 21, 2019 7 days All inclusive
Reg. $2,095
From $1,655 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 38%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,365
From $845 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 34%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,395
From $915 taxes and fees incl.
Prefer another date?
Save up to 35%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,465
From $945 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 34%!
Windsor to Cayo Santa Maria
Tue, January 8, 2019 7 days All inclusive
Reg. $1,445
From $955 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 33%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,435
From $965 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 27%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,445
From $1,055 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 29%!
Windsor to Cayo Santa Maria
Tue, January 8, 2019 7 days All inclusive
Reg. $1,535
From $1,095 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 23%!
Windsor to Riviera Maya
Mon, January 21, 2019 7 days All inclusive
Reg. $2,085
From $1,615 taxes and fees incl.
Prefer another date?
Save up to 23%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,145
From $1,645 taxes and fees incl.
Prefer another date?
Save up to 19%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,235
From $1,805 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 42%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,345
From $785 taxes and fees incl.
Prefer another date?
Save up to 35%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,465
From $945 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 20%!
Windsor to Varadero
Thu, November 22, 2018 7 days All inclusive
Reg. $1,235
From $985 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 20%!
Windsor to Varadero
Thu, November 22, 2018 7 days All inclusive
Reg. $1,265
From $1,015 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 43%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,805
From $1,025 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 16%!
Windsor to Havana
Thu, November 22, 2018 7 days Continental Plan
Reg. $1,345
From $1,125 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Varadero
Thu, December 6, 2018 7 days All inclusive
Reg. $1,625
From $1,145 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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