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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 29%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,465
From $1,035 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 24%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,775
From $1,345 taxes and fees incl.
Prefer another date?
Save up to 25%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,965
From $1,465 taxes and fees incl.
Prefer another date?
Save up to 22%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,015
From $1,565 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 24%!
Windsor to Cancun
Mon, January 18, 2021 7 days All inclusive
Reg. $2,105
From $1,605 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 23%!
Windsor to Cancun
Mon, January 18, 2021 7 days All inclusive
Reg. $2,085
From $1,605 taxes and fees incl.
Prefer another date?
Save up to 19%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $2,075
From $1,685 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 24%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $2,265
From $1,715 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 15%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $2,025
From $1,725 taxes and fees incl.
Prefer another date?
Save up to 28%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $2,435
From $1,755 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 9%!
Windsor to Riviera Maya
Mon, December 14, 2020 7 days All inclusive
Reg. $1,935
From $1,765 taxes and fees incl.
Prefer another date?
Save up to 20%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,275
From $1,825 taxes and fees incl.
Prefer another date?
Save up to 21%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,315
From $1,825 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 33%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,285
From $855 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 35%!
Windsor to Cayo Santa Maria
Tue, December 15, 2020 7 days All inclusive
Reg. $1,375
From $895 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 32%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,345
From $915 taxes and fees incl.
Prefer another date?
Save up to 31%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,385
From $955 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 31%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,385
From $955 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 30%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,435
From $1,005 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 30%!
Windsor to Cayo Santa Maria
Tue, January 19, 2021 7 days All inclusive
Reg. $1,565
From $1,095 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,215
From $1,545 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 24%!
Windsor to Cancun
Mon, January 18, 2021 7 days All inclusive
Reg. $2,105
From $1,605 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 16%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $2,075
From $1,735 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 22%!
Windsor to Cancun
Mon, January 18, 2021 7 days All inclusive
Reg. $2,245
From $1,755 taxes and fees incl.
Prefer another date?
Save up to 20%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,275
From $1,825 taxes and fees incl.
Prefer another date?
Save up to 27%!
Windsor to Cancun
Mon, January 18, 2021 7 days All inclusive
Reg. $1,945
From $1,425 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 29%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,065
From $1,465 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 28%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,025
From $1,465 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 22%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $1,885
From $1,465 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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