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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 32%!
Windsor to Varadero
Thu, January 9, 2020 7 days All inclusive
Reg. $1,665
From $1,125 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 31%!
Windsor to Varadero
Thu, January 9, 2020 7 days All inclusive
Reg. $1,745
From $1,205 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 $1,715 taxes and fees incl.
Prefer another date?
Save up to 22%!
Windsor to Varadero
Thu, January 9, 2020 7 days All inclusive
Reg. $2,225
From $1,735 taxes and fees incl.
Prefer another date?
Save up to 13%!
Windsor to Riviera Maya
Mon, January 6, 2020 7 days All inclusive
Reg. $2,035
From $1,765 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Jamaica
Sun, January 5, 2020 7 days All inclusive
Reg. $2,865
From $1,805 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. $2,025
From $1,805 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 11%!
Windsor to Cancun
Mon, January 6, 2020 7 days All inclusive
Reg. $2,055
From $1,835 taxes and fees incl.
Prefer another date?
Save up to 13%!
Windsor to Riviera Maya
Mon, January 6, 2020 7 days All inclusive
Reg. $2,155
From $1,865 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 39%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,325
From $805 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,475
From $865 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 37%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,445
From $905 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 39%!
Windsor to Cayo Santa Maria
Tue, December 17, 2019 7 days All inclusive
Reg. $1,525
From $925 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 37%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,495
From $935 taxes and fees incl.
Prefer another date?
Save up to 22%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,195
From $935 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 47%!
Windsor to Cayo Santa Maria
Tue, December 17, 2019 7 days All inclusive
Reg. $1,845
From $975 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 34%!
Windsor to Varadero
Thu, December 12, 2019 7 days All inclusive
Reg. $1,585
From $1,045 taxes and fees incl.
Prefer another date?
Save up to 39%!
Windsor to Jamaica
Sun, December 15, 2019 7 days All inclusive
Reg. $2,275
From $1,395 taxes and fees incl.
Prefer another date?
Save up to 38%!
Windsor to Jamaica
Sun, December 15, 2019 7 days All inclusive
Reg. $2,395
From $1,495 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 15%!
Windsor to Cancun
Mon, December 16, 2019 7 days All inclusive
Reg. $2,005
From $1,705 taxes and fees incl.
Prefer another date?
Save up to 39%!
Windsor to Jamaica
Sun, December 15, 2019 7 days All inclusive
Reg. $2,275
From $1,395 taxes and fees incl.
Prefer another date?
Save up to 38%!
Windsor to Jamaica
Sun, December 15, 2019 7 days All inclusive
Reg. $2,395
From $1,495 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 31%!
Windsor to Jamaica
Sun, December 15, 2019 7 days All inclusive
Reg. $2,205
From $1,525 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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