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#1 for Family Vacations

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Largest offering of TripAdvisor’s® top-rated family resorts
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Kids Stay, Play, and Eat FREE
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Family rooms that accommodate 5 or more

Experience the Difference with the #1 for family vacations!  With the most Trip Advisor top-rated all inclusive family resorts in the Caribbean, Mexico, and Central America, free access to the largest waterparks in the Caribbean, the widest selection  of  resorts that accommodate families of five and Where Kids Stay, Play and Eat FREE ,  it’s no wonder we’re #1 to the sun!

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!
Save up to 42%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,245
From $1,295 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 31%!
Windsor to Cayo Coco
Tue, March 27, 2018 7 days All inclusive
Reg. $1,885
From $1,305 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 27%!
Windsor to Varadero
Thu, April 5, 2018 7 days All inclusive
Reg. $1,875
From $1,365 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 43%!
Windsor to Cancun
Mon, March 5, 2018 7 days All inclusive
Reg. $2,395
From $1,365 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 46%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,545
From $1,375 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Riviera Maya
Mon, March 5, 2018 7 days All inclusive
Reg. $2,395
From $1,405 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 31%!
Windsor to Cancun
Mon, April 2, 2018 7 days All inclusive
Reg. $2,105
From $1,455 taxes and fees incl.
Prefer another date?
Save up to 47%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,825
From $1,485 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Riviera Maya
Mon, March 5, 2018 7 days All inclusive
Reg. $2,505
From $1,575 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 41%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,685
From $1,575 taxes and fees incl.
Prefer another date?
Save up to 39%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,665
From $1,625 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 37%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,645
From $1,655 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 21%!
Windsor to Varadero
Thu, April 5, 2018 7 days All inclusive
Reg. $2,185
From $1,725 taxes and fees incl.
Prefer another date?
Save up to 34%!
Windsor to Jamaica
Sun, February 25, 2018 7 days All inclusive
Reg. $2,665
From $1,765 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $3,125
From $1,855 taxes and fees incl.
Prefer another date?
Save up to 28%!
Windsor to Jamaica
Sun, February 25, 2018 7 days All inclusive
Reg. $2,715
From $1,945 taxes and fees incl.
Prefer another date?
Save up to 36%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $3,085
From $1,965 taxes and fees incl.
Prefer another date?
Save up to 33%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $3,145
From $2,095 taxes and fees incl.
Prefer another date?
Save up to 23%!
Windsor to Cancun
Mon, February 26, 2018 7 days All inclusive
Reg. $2,995
From $2,305 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 47%!
Windsor to Varadero
Thu, March 15, 2018 7 days All inclusive
Reg. $1,555
From $825 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 17%!
Windsor to Varadero
Thu, March 29, 2018 7 days All inclusive
Reg. $1,145
From $945 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 39%!
Windsor to Cayo Coco
Tue, February 27, 2018 7 days All inclusive
Reg. $1,625
From $985 taxes and fees incl.
Prefer another date?
Save up to 26%!
Windsor to Varadero
Thu, March 29, 2018 7 days All inclusive
Reg. $1,335
From $985 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 31%!
Windsor to Varadero
Thu, March 29, 2018 7 days All inclusive
Reg. $1,475
From $1,015 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 26%!
Windsor to Cayo Coco
Tue, April 3, 2018 7 days All inclusive
Reg. $1,415
From $1,045 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 36%!
Windsor to Varadero
Thu, March 1, 2018 7 days All inclusive
Reg. $1,705
From $1,085 taxes and fees incl.
Prefer another date?
Save up to 27%!
Windsor to Cayo Coco
Tue, April 3, 2018 7 days All inclusive
Reg. $1,505
From $1,095 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,165
From $1,275 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 22%!
Windsor to Cancun
Mon, March 19, 2018 7 days All inclusive
Reg. $1,825
From $1,425 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Cancun
Mon, March 19, 2018 7 days All inclusive
Reg. $2,095
From $1,465 taxes and fees incl.
Prefer another date?
Save up to 49%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,555
From $1,295 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 42%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,335
From $1,345 taxes and fees incl.
Prefer another date?
Save up to 47%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,825
From $1,485 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $3,125
From $1,855 taxes and fees incl.
Prefer another date?
Save up to 28%!
Windsor to Jamaica
Sun, February 25, 2018 7 days All inclusive
Reg. $2,715
From $1,945 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 40%!
Windsor to Varadero
Thu, March 15, 2018 7 days All inclusive
Reg. $1,255
From $755 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 13%!
Windsor to Cayo Coco
Tue, March 27, 2018 7 days All inclusive
Reg. $1,115
From $965 taxes and fees incl.
Prefer another date?
Save up to 26%!
Windsor to Varadero
Thu, March 29, 2018 7 days All inclusive
Reg. $1,335
From $985 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 28%!
Windsor to Varadero
Thu, March 29, 2018 7 days All inclusive
Reg. $1,455
From $1,045 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 41%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days Breakfast Plan
Reg. $1,775
From $1,055 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 22%!
Windsor to Varadero
Thu, March 15, 2018 7 days All inclusive
Reg. $1,425
From $1,115 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 16%!
Windsor to Varadero
Thu, April 5, 2018 7 days All inclusive
Reg. $1,385
From $1,165 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 14%!
Windsor to Cayo Coco
Tue, March 27, 2018 7 days All inclusive
Reg. $1,395
From $1,205 taxes and fees incl.
Prefer another date?
Save up to 40%!
Windsor to Jamaica
Sun, March 4, 2018 7 days Inclusive
Reg. $1,995
From $1,205 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 64%!
Windsor to Cancun
Mon, March 5, 2018 7 days All inclusive
Reg. $3,365
From $1,215 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 29%!
Windsor to Jamaica
Sun, March 25, 2018 7 days European Plan
Reg. $1,715
From $1,225 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 41%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,125
From $1,245 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Varadero
Thu, March 29, 2018 7 days All inclusive
Reg. $1,795
From $1,255 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 15%!
Windsor to Havana
Thu, March 15, 2018 7 days Continental Plan
Reg. $1,475
From $1,255 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 60%!
Windsor to Cancun
Mon, February 26, 2018 7 days All inclusive
Reg. $3,195
From $1,265 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,165
From $1,275 taxes and fees incl.
Prefer another date?
Save up to 58%!
Windsor to Riviera Maya
Mon, March 5, 2018 7 days All inclusive
Reg. $3,165
From $1,315 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 42%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,335
From $1,345 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 35%!
Windsor to Varadero
Thu, March 29, 2018 7 days All inclusive
Reg. $2,095
From $1,365 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 46%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,545
From $1,375 taxes and fees incl.
Prefer another date?
Save up to 41%!
Windsor to Riviera Maya
Mon, March 5, 2018 7 days All inclusive
Reg. $2,395
From $1,405 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 22%!
Windsor to Cancun
Mon, March 19, 2018 7 days All inclusive
Reg. $1,825
From $1,425 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 50%!
Windsor to Cancun
Mon, February 26, 2018 7 days All inclusive
Reg. $2,865
From $1,445 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Cancun
Mon, March 19, 2018 7 days All inclusive
Reg. $2,095
From $1,465 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,355
From $1,475 taxes and fees incl.
Prefer another date?
Save up to 47%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,825
From $1,485 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 47%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,875
From $1,525 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 23%!
Windsor to Cancun
Mon, March 19, 2018 7 days All inclusive
Reg. $2,005
From $1,535 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Riviera Maya
Mon, March 5, 2018 7 days All inclusive
Reg. $2,505
From $1,575 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 41%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $2,685
From $1,575 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 41%!
Windsor to Riviera Maya
Mon, March 5, 2018 7 days American Plan
Reg. $2,685
From $1,575 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 33%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,365
From $1,585 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 31%!
Windsor to Jamaica
Sun, March 4, 2018 7 days All inclusive
Reg. $2,315
From $1,605 taxes and fees incl.
Prefer another date?
Save up to 44%!
Windsor to Cancun
Mon, February 26, 2018 7 days All inclusive
Reg. $2,845
From $1,605 taxes and fees incl.
Prefer another date?
Save up to 35%!
Windsor to Riviera Maya
Mon, March 5, 2018 7 days All inclusive
Reg. $2,485
From $1,605 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 46%!
Windsor to Riviera Maya
Mon, February 26, 2018 7 days All inclusive
Reg. $3,025
From $1,625 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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