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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

Varadero, Cuba
Save up to 32%!
Windsor to Varadero
Thu, March 19, 2020 7 days All inclusive
Reg. $1,805
From $1,225 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 34%!
Windsor to Varadero
Thu, March 19, 2020 7 days All inclusive
Reg. $1,985
From $1,305 taxes and fees incl.
Prefer another date?
Save up to 28%!
Windsor to Varadero
Thu, March 19, 2020 7 days All inclusive
Reg. $2,405
From $1,725 taxes and fees incl.
Prefer another date?
Save up to 21%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,235
From $1,755 taxes and fees incl.
Prefer another date?
Save up to 23%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,355
From $1,805 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 13%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,085
From $1,815 taxes and fees incl.
Prefer another date?
Save up to 33%!
Windsor to Jamaica
Sun, March 8, 2020 7 days All inclusive
Reg. $2,775
From $1,865 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 16%!
Windsor to Cancun
Mon, March 9, 2020 7 days All inclusive
Reg. $2,245
From $1,895 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 21%!
Windsor to Cancun
Mon, March 9, 2020 7 days All inclusive
Reg. $2,405
From $1,895 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 30%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,705
From $1,905 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 19%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,405
From $1,945 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 13%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,295
From $1,995 taxes and fees incl.
Prefer another date?
Save up to 27%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,765
From $2,005 taxes and fees incl.
Prefer another date?
Save up to 17%!
Windsor to Jamaica
Sun, February 9, 2020 7 days All inclusive
Reg. $2,515
From $2,095 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 33%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,405
From $945 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 28%!
Windsor to Varadero
Thu, April 2, 2020 7 days All inclusive
Reg. $1,375
From $985 taxes and fees incl.
Prefer another date?
Save up to 36%!
Windsor to Varadero
Thu, April 2, 2020 7 days All inclusive
Reg. $1,575
From $1,005 taxes and fees incl.
Prefer another date?
Save up to 36%!
Windsor to Varadero
Thu, March 19, 2020 7 days All inclusive
Reg. $1,585
From $1,015 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 32%!
Windsor to Varadero
Thu, April 2, 2020 7 days All inclusive
Reg. $1,575
From $1,065 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 26%!
Windsor to Varadero
Thu, April 2, 2020 7 days All inclusive
Reg. $1,445
From $1,075 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 30%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,555
From $1,095 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 29%!
Windsor to Varadero
Thu, April 2, 2020 7 days All inclusive
Reg. $1,565
From $1,105 taxes and fees incl.
Prefer another date?
Save up to 44%!
Windsor to Jamaica
Sun, February 9, 2020 7 days All inclusive
Reg. $3,145
From $1,755 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 17%!
Windsor to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,125
From $1,765 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Jamaica
Sun, February 9, 2020 7 days All inclusive
Reg. $3,135
From $1,835 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 16%!
Windsor to Cancun
Mon, March 9, 2020 7 days All inclusive
Reg. $2,245
From $1,895 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 39%!
Windsor to Jamaica
Sun, February 2, 2020 7 days All inclusive
Reg. $2,685
From $1,625 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 43%!
Windsor to Jamaica
Sun, February 2, 2020 7 days All inclusive
Reg. $2,865
From $1,645 taxes and fees incl.
Prefer another date?
Save up to 20%!
Windsor to Cancun
Mon, March 9, 2020 7 days All inclusive
Reg. $2,055
From $1,635 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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