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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, April 4, 2019 7 days All inclusive
Reg. $1,775
From $1,355 taxes and fees incl.
Prefer another date?
Save up to 36%!
Windsor to Riviera Maya
Mon, March 18, 2019 7 days All inclusive
Reg. $2,185
From $1,395 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 32%!
Windsor to Cancun
Mon, March 18, 2019 7 days All inclusive
Reg. $2,325
From $1,575 taxes and fees incl.
Prefer another date?
Save up to 32%!
Windsor to Riviera Maya
Mon, March 18, 2019 7 days All inclusive
Reg. $2,305
From $1,575 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Jamaica
Sun, February 24, 2019 7 days All inclusive
Reg. $2,775
From $1,635 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 31%!
Windsor to Cancun
Mon, March 18, 2019 7 days All inclusive
Reg. $2,355
From $1,635 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 38%!
Windsor to Riviera Maya
Mon, March 18, 2019 7 days All inclusive
Reg. $2,665
From $1,645 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Riviera Maya
Mon, March 18, 2019 7 days All inclusive
Reg. $2,675
From $1,675 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 21%!
Windsor to Riviera Maya
Mon, March 18, 2019 7 days All inclusive
Reg. $2,125
From $1,685 taxes and fees incl.
Prefer another date?
Save up to 33%!
Windsor to Riviera Maya
Mon, March 18, 2019 7 days All inclusive
Reg. $2,575
From $1,735 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 33%!
Windsor to Cayo Santa Maria
Tue, April 2, 2019 7 days All inclusive
Reg. $1,405
From $935 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 13%!
Windsor to Varadero
Thu, March 14, 2019 7 days All inclusive
Reg. $1,165
From $1,015 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 34%!
Windsor to Varadero
Thu, March 14, 2019 7 days All inclusive
Reg. $1,575
From $1,045 taxes and fees incl.
Prefer another date?
Save up to 16%!
Windsor to Varadero
Thu, April 4, 2019 7 days All inclusive
Reg. $1,275
From $1,075 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 35%!
Windsor to Varadero
Thu, March 14, 2019 7 days All inclusive
Reg. $1,695
From $1,095 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 36%!
Windsor to Cayo Santa Maria
Tue, March 26, 2019 7 days All inclusive
Reg. $1,715
From $1,095 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 20%!
Windsor to Varadero
Thu, April 4, 2019 7 days All inclusive
Reg. $1,435
From $1,155 taxes and fees incl.
Prefer another date?
Save up to 47%!
Windsor to Jamaica
Sun, March 3, 2019 7 days All inclusive
Reg. $2,695
From $1,415 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 28%!
Windsor to Riviera Maya
Mon, March 25, 2019 7 days All inclusive
Reg. $2,145
From $1,535 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Jamaica
Sun, February 24, 2019 7 days All inclusive
Reg. $2,775
From $1,635 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 30%!
Windsor to Cancun
Mon, March 18, 2019 7 days All inclusive
Reg. $2,535
From $1,785 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 35%!
Windsor to Varadero
Thu, March 14, 2019 7 days All inclusive
Reg. $1,395
From $905 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 41%!
Windsor to Jamaica
Sun, March 24, 2019 7 days European Plan
Reg. $1,815
From $1,075 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 18%!
Windsor to Havana
Thu, March 14, 2019 7 days Continental Plan
Reg. $1,235
From $1,015 taxes and fees incl.
Prefer another date?
Save up to 16%!
Windsor to Varadero
Thu, April 4, 2019 7 days All inclusive
Reg. $1,275
From $1,075 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 32%!
Windsor to Riviera Maya
Mon, March 18, 2019 7 days Breakfast Plan
Reg. $1,645
From $1,115 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 20%!
Windsor to Varadero
Thu, April 4, 2019 7 days All inclusive
Reg. $1,475
From $1,175 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Varadero
Thu, March 14, 2019 7 days All inclusive
Reg. $1,895
From $1,195 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 29%!
Windsor to Varadero
Thu, April 4, 2019 7 days All inclusive
Reg. $1,715
From $1,225 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 29%!
Windsor to Varadero
Thu, April 4, 2019 7 days All inclusive
Reg. $1,745
From $1,235 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Jamaica
Sun, March 24, 2019 7 days Inclusive
Reg. $1,955
From $1,365 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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