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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 44%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,835
From $1,035 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,235
From $1,405 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 20%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,685
From $1,345 taxes and fees incl.
Prefer another date?
Save up to 25%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $2,035
From $1,535 taxes and fees incl.
Prefer another date?
Save up to 38%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,625
From $1,615 taxes and fees incl.
Prefer another date?
Save up to 24%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $2,155
From $1,635 taxes and fees incl.
Prefer another date?
Save up to 14%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,025
From $1,745 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 24%!
Windsor to Cancun
Mon, January 7, 2019 7 days All inclusive
Reg. $2,245
From $1,715 taxes and fees incl.
Prefer another date?
Save up to 31%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $2,495
From $1,725 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 6%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $1,855
From $1,745 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 21%!
Windsor to Cancun
Mon, January 7, 2019 7 days All inclusive
Reg. $2,195
From $1,745 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 12%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $2,055
From $1,805 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 25%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $2,455
From $1,835 taxes and fees incl.
Prefer another date?
Save up to 24%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $2,435
From $1,855 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 46%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,365
From $735 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 44%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,465
From $825 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 42%!
Windsor to Cayo Santa Maria
Tue, January 15, 2019 7 days All inclusive
Reg. $1,445
From $845 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 42%!
Windsor to Cayo Santa Maria
Tue, January 15, 2019 7 days All inclusive
Reg. $1,535
From $895 taxes and fees incl.
Prefer another date?
Save up to 17%!
Windsor to Varadero
Thu, January 17, 2019 7 days All inclusive
Reg. $1,085
From $905 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 37%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,485
From $935 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 32%!
Windsor to Varadero
Thu, January 17, 2019 7 days All inclusive
Reg. $1,495
From $1,015 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,235
From $1,405 taxes and fees incl.
Prefer another date?
Save up to 39%!
Windsor to Jamaica
Sun, January 20, 2019 7 days All inclusive
Reg. $2,825
From $1,725 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 25%!
Windsor to Cancun
Mon, January 7, 2019 7 days All inclusive
Reg. $2,345
From $1,755 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 18%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days All inclusive
Reg. $2,165
From $1,785 taxes and fees incl.
Prefer another date?
Save up to 34%!
Windsor to Jamaica
Sun, January 20, 2019 7 days All inclusive
Reg. $3,015
From $1,985 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 48%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,445
From $755 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 53%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,835
From $865 taxes and fees incl.
Prefer another date?
Save up to 17%!
Windsor to Varadero
Thu, January 17, 2019 7 days All inclusive
Reg. $1,085
From $905 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 46%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,675
From $905 taxes and fees incl.
Prefer another date?
Save up to 46%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,665
From $905 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 26%!
Windsor to Varadero
Thu, January 17, 2019 7 days All inclusive
Reg. $1,395
From $1,035 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 31%!
Windsor to Riviera Maya
Mon, January 7, 2019 7 days Breakfast Plan
Reg. $1,575
From $1,085 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 17%!
Windsor to Havana
Thu, December 13, 2018 7 days Continental Plan
Reg. $1,325
From $1,105 taxes and fees incl.
Prefer another date?
Save up to 34%!
Windsor to Jamaica
Sun, December 16, 2018 7 days Inclusive
Reg. $1,845
From $1,215 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 50%!
Windsor to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $2,275
From $1,135 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 42%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,145
From $1,235 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 35%!
Windsor to Jamaica
Sun, January 20, 2019 7 days European Plan
Reg. $1,965
From $1,285 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 36%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,125
From $1,355 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Jamaica
Sun, December 16, 2018 7 days All inclusive
Reg. $2,235
From $1,405 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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