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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 24%!
Windsor to Varadero
Thu, January 16, 2020 7 days All inclusive
Reg. $1,715
From $1,305 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 18%!
Windsor to Varadero
Thu, January 9, 2020 7 days All inclusive
Reg. $1,745
From $1,435 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 8%!
Windsor to Riviera Maya
Mon, January 6, 2020 7 days All inclusive
Reg. $1,805
From $1,655 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 10%!
Windsor to Riviera Maya
Mon, January 6, 2020 7 days All inclusive
Reg. $1,875
From $1,685 taxes and fees incl.
Prefer another date?
Save up to 18%!
Windsor to Riviera Maya
Mon, January 20, 2020 7 days All inclusive
Reg. $2,085
From $1,705 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 11%!
Windsor to Riviera Maya
Mon, January 6, 2020 7 days All inclusive
Reg. $1,925
From $1,705 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 16%!
Windsor to Cancun
Mon, January 20, 2020 7 days All inclusive
Reg. $2,105
From $1,775 taxes and fees incl.
Prefer another date?
Save up to 17%!
Windsor to Riviera Maya
Mon, January 20, 2020 7 days All inclusive
Reg. $2,205
From $1,825 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 14%!
Windsor to Cancun
Mon, January 20, 2020 7 days All inclusive
Reg. $2,235
From $1,915 taxes and fees incl.
Prefer another date?
Save up to 15%!
Windsor to Varadero
Thu, January 16, 2020 7 days All inclusive
Reg. $2,265
From $1,915 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Jamaica
Sun, January 5, 2020 7 days All inclusive
Reg. $2,865
From $2,005 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 29%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,325
From $935 taxes and fees incl.
Prefer another date?
Save up to 34%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,475
From $975 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 31%!
Windsor to Cayo Santa Maria
Tue, January 21, 2020 7 days All inclusive
Reg. $1,485
From $1,025 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 28%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,445
From $1,045 taxes and fees incl.
Prefer another date?
Save up to 9%!
Windsor to Varadero
Thu, December 5, 2019 7 days All inclusive
Reg. $1,195
From $1,085 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 27%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,495
From $1,095 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 21%!
Windsor to Riviera Maya
Mon, December 16, 2019 7 days All inclusive
Reg. $1,955
From $1,545 taxes and fees incl.
Prefer another date?
Save up to 20%!
Windsor to Jamaica
Sun, December 15, 2019 7 days All inclusive
Reg. $2,125
From $1,705 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 14%!
Windsor to Cancun
Mon, December 16, 2019 7 days All inclusive
Reg. $2,005
From $1,725 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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