Skip Navigation

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

Puerto Plata, Dominican Republic
Save up to 33%!
Winnipeg to Puerto Plata
Wed, November 4, 2020 7 days All inclusive
Reg. $1,625
From $1,095 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 28%!
Winnipeg to Cayo Coco
Sat, December 12, 2020 7 days All inclusive
Reg. $1,745
From $1,265 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 31%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,875
From $1,295 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 25%!
Winnipeg to Varadero
Tue, January 26, 2021 7 days All inclusive
Reg. $1,725
From $1,295 taxes and fees incl.
Prefer another date?
Save up to 20%!
Winnipeg to Holguin
Fri, January 8, 2021 7 days All inclusive
Reg. $1,635
From $1,315 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 34%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $2,095
From $1,385 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 29%!
Winnipeg to Riviera Maya
Mon, November 9, 2020 7 days All inclusive
Reg. $1,975
From $1,405 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 25%!
Winnipeg to Varadero
Tue, January 19, 2021 7 days All inclusive
Reg. $1,875
From $1,415 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 29%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $2,045
From $1,445 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $2,405
From $1,465 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 19%!
Winnipeg to Riviera Nayarit
Sun, December 13, 2020 7 days All inclusive
Reg. $1,835
From $1,495 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 24%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $1,975
From $1,495 taxes and fees incl.
Prefer another date?
Save up to 29%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $2,105
From $1,505 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 26%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $2,055
From $1,515 taxes and fees incl.
Prefer another date?
Save up to 26%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $2,055
From $1,515 taxes and fees incl.
Prefer another date?
Save up to 35%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $2,325
From $1,515 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 7%!
Winnipeg to Mazatlán
Fri, December 11, 2020 7 days All inclusive
Reg. $1,665
From $1,545 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 12%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,785
From $1,565 taxes and fees incl.
Prefer another date?
Save up to 25%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $2,075
From $1,565 taxes and fees incl.
Prefer another date?
La Romana, Dominican Republic
Save up to 12%!
Winnipeg to La Romana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,805
From $1,585 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 32%!
Winnipeg to Puerto Plata
Wed, November 4, 2020 7 days All inclusive
Reg. $1,425
From $975 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 31%!
Winnipeg to Puerto Plata
Wed, November 4, 2020 7 days All inclusive
Reg. $1,495
From $1,035 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 27%!
Winnipeg to Varadero
Tue, January 5, 2021 7 days All inclusive
Reg. $1,415
From $1,035 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 27%!
Winnipeg to Cayo Santa Maria
Fri, December 4, 2020 7 days All inclusive
Reg. $1,465
From $1,065 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 33%!
Winnipeg to Puerto Plata
Wed, November 4, 2020 7 days All inclusive
Reg. $1,625
From $1,095 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 26%!
Winnipeg to Varadero
Tue, January 5, 2021 7 days All inclusive
Reg. $1,485
From $1,105 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 28%!
Winnipeg to Cayo Coco
Sat, December 12, 2020 7 days All inclusive
Reg. $1,545
From $1,105 taxes and fees incl.
Prefer another date?
Save up to 25%!
Winnipeg to Varadero
Tue, January 5, 2021 7 days All inclusive
Reg. $1,515
From $1,135 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 24%!
Winnipeg to Cayo Coco
Sat, December 12, 2020 7 days All inclusive
Reg. $1,495
From $1,135 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 26%!
Winnipeg to Varadero
Tue, January 5, 2021 7 days All inclusive
Reg. $1,555
From $1,155 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 16%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,385
From $1,165 taxes and fees incl.
Prefer another date?
La Romana, Dominican Republic
Save up to 15%!
Winnipeg to La Romana
Wed, November 4, 2020 7 days European Plan
Reg. $1,455
From $1,235 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 23%!
Winnipeg to Cayo Coco
Sat, December 12, 2020 7 days All inclusive
Reg. $1,605
From $1,235 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 25%!
Winnipeg to Varadero
Tue, January 5, 2021 7 days All inclusive
Reg. $1,665
From $1,255 taxes and fees incl.
Prefer another date?
Santo Domingo, Dominican Republic
Save up to 14%!
Winnipeg to Santo Domingo
Wed, November 4, 2020 7 days All inclusive
Reg. $1,545
From $1,325 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 33%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,815
From $1,215 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 31%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,875
From $1,295 taxes and fees incl.
Prefer another date?
Save up to 32%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,975
From $1,345 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 34%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $2,095
From $1,385 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 28%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $1,955
From $1,405 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 33%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $2,125
From $1,415 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 13%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,655
From $1,435 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 31%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $2,125
From $1,465 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 27%!
Winnipeg to Punta Cana
Wed, November 25, 2020 7 days All inclusive
Reg. $2,075
From $1,515 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 30%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $2,215
From $1,545 taxes and fees incl.
Prefer another date?
Save up to 33%!
Winnipeg to Jamaica
Mon, December 7, 2020 7 days All inclusive
Reg. $2,435
From $1,625 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 11%!
Winnipeg to Los Cabos
Thu, December 17, 2020 7 days All inclusive
Reg. $1,995
From $1,775 taxes and fees incl.
Prefer another date?
Save up to 24%!
Winnipeg to Jamaica
Mon, December 7, 2020 7 days All inclusive
Reg. $2,495
From $1,905 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 27%!
Winnipeg to Puerto Plata
Wed, November 4, 2020 7 days All inclusive
Reg. $1,465
From $1,065 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 25%!
Winnipeg to Cayo Coco
Sat, December 12, 2020 7 days All inclusive
Reg. $1,455
From $1,085 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 16%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,385
From $1,165 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 33%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $1,885
From $1,255 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 31%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $1,875
From $1,295 taxes and fees incl.
Prefer another date?
Save up to 27%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $1,855
From $1,345 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 34%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $2,095
From $1,385 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 28%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $1,955
From $1,405 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 29%!
Winnipeg to Riviera Maya
Mon, November 9, 2020 7 days All inclusive
Reg. $1,975
From $1,405 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 30%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $1,995
From $1,405 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 33%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $2,125
From $1,415 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 30%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $2,035
From $1,415 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 26%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $1,955
From $1,445 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 29%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $2,045
From $1,445 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 29%!
Winnipeg to Cancun
Sat, December 12, 2020 7 days All inclusive
Reg. $2,025
From $1,445 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 18%!
Winnipeg to Riviera Nayarit
Sun, December 13, 2020 7 days All inclusive
Reg. $1,785
From $1,455 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 37%!
Winnipeg to Riviera Maya
Sat, December 12, 2020 7 days All inclusive
Reg. $2,325
From $1,455 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 31%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $2,125
From $1,465 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 27%!
Winnipeg to Punta Cana
Wed, November 25, 2020 7 days All inclusive
Reg. $2,075
From $1,515 taxes and fees incl.
Prefer another date?
Save up to 26%!
Winnipeg to Punta Cana
Wed, November 4, 2020 7 days All inclusive
Reg. $2,055
From $1,515 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.

Back to
top