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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 44%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,945
From $1,085 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 39%!
Winnipeg to Cayo Coco
Sat, December 15, 2018 7 days All inclusive
Reg. $1,795
From $1,095 taxes and fees incl.
Prefer another date?
Save up to 34%!
Winnipeg to Holguin
Fri, January 18, 2019 7 days All inclusive
Reg. $1,785
From $1,175 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 45%!
Winnipeg to Riviera Nayarit
Fri, December 14, 2018 7 days All inclusive
Reg. $2,245
From $1,225 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 31%!
Winnipeg to Mazatlán
Fri, January 4, 2019 7 days All inclusive
Reg. $1,795
From $1,235 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,025
From $1,235 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 44%!
Winnipeg to Riviera Maya
Mon, December 17, 2018 7 days All inclusive
Reg. $2,255
From $1,255 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 38%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,095
From $1,295 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 39%!
Winnipeg to Cancun
Sat, December 15, 2018 7 days All inclusive
Reg. $2,185
From $1,325 taxes and fees incl.
Prefer another date?
Save up to 47%!
Winnipeg to Riviera Maya
Wed, December 19, 2018 7 days All inclusive
Reg. $2,525
From $1,335 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 41%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,475
From $1,455 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 22%!
Winnipeg to Varadero
Sat, December 15, 2018 7 days All inclusive
Reg. $1,765
From $1,385 taxes and fees incl.
Prefer another date?
Save up to 53%!
Winnipeg to Huatulco
Tue, December 18, 2018 7 days All inclusive
Reg. $3,125
From $1,465 taxes and fees incl.
Prefer another date?
Save up to 30%!
Winnipeg to Mazatlán
Fri, January 25, 2019 7 days All inclusive
Reg. $2,095
From $1,475 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 25%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, January 20, 2019 7 days All inclusive
Reg. $1,995
From $1,495 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 21%!
Winnipeg to Riviera Nayarit
Fri, January 4, 2019 7 days All inclusive
Reg. $1,945
From $1,535 taxes and fees incl.
Prefer another date?
Save up to 41%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,695
From $1,585 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 38%!
Winnipeg to Los Cabos
Thu, December 20, 2018 7 days All inclusive
Reg. $2,575
From $1,595 taxes and fees incl.
Prefer another date?
Save up to 48%!
Winnipeg to Riviera Maya
Mon, December 17, 2018 7 days All inclusive
Reg. $3,065
From $1,605 taxes and fees incl.
Prefer another date?
Save up to 29%!
Winnipeg to Jamaica
Mon, December 17, 2018 7 days All inclusive
Reg. $2,405
From $1,705 taxes and fees incl.
Prefer another date?
Save up to 32%!
Winnipeg to Riviera Maya
Wed, January 2, 2019 7 days All inclusive
Reg. $2,445
From $1,655 taxes and fees incl.
Prefer another date?
Save up to 42%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,915
From $1,705 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 29%!
Winnipeg to Cancun
Wed, January 2, 2019 7 days All inclusive
Reg. $2,485
From $1,755 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 34%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,785
From $1,825 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 24%!
Winnipeg to Los Cabos
Thu, January 3, 2019 7 days All inclusive
Reg. $2,315
From $1,765 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 25%!
Winnipeg to Punta Cana
Wed, January 9, 2019 7 days All inclusive
Reg. $2,485
From $1,865 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 11%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,085
From $1,865 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 29%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,625
From $1,875 taxes and fees incl.
Prefer another date?
Save up to 31%!
Winnipeg to Jamaica
Mon, December 17, 2018 7 days All inclusive
Reg. $2,775
From $1,915 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 39%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $3,135
From $1,915 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 47%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,485
From $785 taxes and fees incl.
Prefer another date?
Save up to 21%!
Winnipeg to Varadero
Sat, December 15, 2018 7 days All inclusive
Reg. $995
From $785 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 52%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $1,805
From $875 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 49%!
Winnipeg to Cayo Coco
Sat, December 15, 2018 7 days All inclusive
Reg. $1,655
From $845 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 45%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,585
From $875 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 43%!
Winnipeg to Mazatlán
Fri, December 21, 2018 7 days European Plan
Reg. $1,625
From $925 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 13%!
Winnipeg to Cayo Coco
Sat, December 15, 2018 7 days All inclusive
Reg. $1,035
From $905 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 37%!
Winnipeg to Puerto Plata
Thu, March 28, 2019 7 days All inclusive
Reg. $1,655
From $1,045 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 50%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, December 16, 2018 7 days All inclusive
Reg. $2,005
From $1,005 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 47%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $1,875
From $995 taxes and fees incl.
Prefer another date?
Save up to 39%!
Winnipeg to Cayo Coco
Sat, December 15, 2018 7 days All inclusive
Reg. $1,595
From $975 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 38%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,595
From $985 taxes and fees incl.
Prefer another date?
Save up to 41%!
Winnipeg to Holguin
Fri, January 18, 2019 7 days All inclusive
Reg. $1,675
From $995 taxes and fees incl.
Prefer another date?
Save up to 34%!
Winnipeg to Holguin
Fri, January 4, 2019 7 days All inclusive
Reg. $1,505
From $995 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 35%!
Winnipeg to Cayo Santa Maria
Fri, January 11, 2019 7 days All inclusive
Reg. $1,555
From $1,005 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 36%!
Winnipeg to Cayo Santa Maria
Fri, January 11, 2019 7 days All inclusive
Reg. $1,645
From $1,055 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 32%!
Winnipeg to Puerto Plata
Thu, January 10, 2019 7 days All inclusive
Reg. $1,695
From $1,155 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 26%!
Winnipeg to Varadero
Thu, January 3, 2019 7 days All inclusive
Reg. $1,465
From $1,085 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 28%!
Winnipeg to Puerto Plata
Thu, January 10, 2019 7 days All inclusive
Reg. $1,665
From $1,205 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 15%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $1,445
From $1,225 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 42%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $2,055
From $1,185 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 39%!
Winnipeg to Mazatlán
Fri, December 21, 2018 7 days All inclusive
Reg. $1,945
From $1,195 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 42%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $2,055
From $1,195 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 32%!
Winnipeg to Puerto Plata
Thu, January 10, 2019 7 days All inclusive
Reg. $1,855
From $1,265 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 14%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $1,395
From $1,205 taxes and fees incl.
Prefer another date?
Santo Domingo, Dominican Republic
Save up to 15%!
Winnipeg to Santo Domingo
Wed, December 19, 2018 7 days All inclusive
Reg. $1,505
From $1,285 taxes and fees incl.
Prefer another date?
Save up to 44%!
Winnipeg to Cancun
Sat, December 15, 2018 7 days All inclusive
Reg. $2,205
From $1,245 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 38%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,025
From $1,255 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 43%!
Winnipeg to Los Cabos
Thu, December 20, 2018 7 days All inclusive
Reg. $2,185
From $1,235 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 15%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $1,515
From $1,295 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 44%!
Winnipeg to Cancun
Mon, December 17, 2018 7 days All inclusive
Reg. $2,365
From $1,335 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,225
From $1,355 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 25%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $1,915
From $1,445 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 38%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,585
From $1,615 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 38%!
Winnipeg to Los Cabos
Thu, December 20, 2018 7 days All inclusive
Reg. $2,575
From $1,595 taxes and fees incl.
Prefer another date?
Save up to 29%!
Winnipeg to Jamaica
Mon, December 17, 2018 7 days All inclusive
Reg. $2,405
From $1,705 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 33%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,605
From $1,755 taxes and fees incl.
Prefer another date?
Save up to 31%!
Winnipeg to Jamaica
Mon, January 21, 2019 7 days All inclusive
Reg. $2,625
From $1,805 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 29%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,775
From $1,975 taxes and fees incl.
Prefer another date?
Save up to 36%!
Winnipeg to Jamaica
Mon, January 21, 2019 7 days All inclusive
Reg. $3,105
From $1,995 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 53%!
Winnipeg to Riviera Maya
Mon, December 17, 2018 7 days Breakfast Plan
Reg. $1,765
From $825 taxes and fees incl.
Prefer another date?
Save up to 21%!
Winnipeg to Varadero
Sat, December 15, 2018 7 days All inclusive
Reg. $995
From $785 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 48%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,555
From $805 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 54%!
Winnipeg to Riviera Nayarit
Fri, December 14, 2018 7 days All inclusive
Reg. $1,855
From $845 taxes and fees incl.
Prefer another date?
Save up to 53%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $1,805
From $845 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 43%!
Winnipeg to Mazatlán
Fri, December 21, 2018 7 days European Plan
Reg. $1,625
From $925 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 28%!
Winnipeg to Cayo Coco
Sat, December 15, 2018 7 days All inclusive
Reg. $1,265
From $905 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 53%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,945
From $915 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 50%!
Winnipeg to Riviera Maya
Mon, December 17, 2018 7 days All inclusive
Reg. $1,915
From $965 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 56%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, December 16, 2018 7 days All inclusive
Reg. $2,245
From $985 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 46%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $1,785
From $955 taxes and fees incl.
Prefer another date?
Save up to 50%!
Winnipeg to Varadero
Sat, December 15, 2018 7 days All inclusive
Reg. $1,925
From $955 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 49%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $1,955
From $995 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 32%!
Winnipeg to Mazatlán
Fri, January 18, 2019 7 days European Plan
Reg. $1,485
From $1,005 taxes and fees incl.
Prefer another date?
Save up to 41%!
Winnipeg to Holguin
Fri, January 18, 2019 7 days All inclusive
Reg. $1,675
From $995 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 49%!
Winnipeg to Riviera Nayarit
Fri, December 14, 2018 7 days All inclusive
Reg. $2,025
From $1,035 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 30%!
Winnipeg to Cayo Coco
Sat, December 15, 2018 7 days All inclusive
Reg. $1,435
From $1,005 taxes and fees incl.
Prefer another date?
Save up to 54%!
Winnipeg to Riviera Nayarit
Fri, December 14, 2018 7 days All inclusive
Reg. $2,315
From $1,055 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 38%!
Winnipeg to Puerto Plata
Thu, December 20, 2018 7 days All inclusive
Reg. $1,955
From $1,205 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 31%!
Winnipeg to Varadero
Thu, January 3, 2019 7 days All inclusive
Reg. $1,595
From $1,105 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 15%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $1,445
From $1,225 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 43%!
Winnipeg to Punta Cana
Wed, December 19, 2018 7 days All inclusive
Reg. $2,215
From $1,255 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 16%!
Winnipeg to Havana
Thu, December 13, 2018 7 days Continental Plan
Reg. $1,375
From $1,155 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 14%!
Winnipeg to Puerto Vallarta
Fri, December 14, 2018 7 days All inclusive
Reg. $1,395
From $1,205 taxes and fees incl.
Prefer another date?
Santo Domingo, Dominican Republic
Save up to 15%!
Winnipeg to Santo Domingo
Wed, December 19, 2018 7 days All inclusive
Reg. $1,505
From $1,285 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 37%!
Winnipeg to Puerto Plata
Thu, March 7, 2019 7 days All inclusive
Reg. $2,025
From $1,285 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 51%!
Winnipeg to Varadero
Thu, December 13, 2018 7 days All inclusive
Reg. $2,395
From $1,185 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 50%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, December 16, 2018 7 days All inclusive
Reg. $2,485
From $1,235 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 45%!
Winnipeg to Riviera Nayarit
Fri, December 14, 2018 7 days All inclusive
Reg. $2,245
From $1,225 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 31%!
Winnipeg to Mazatlán
Fri, January 4, 2019 7 days All inclusive
Reg. $1,795
From $1,235 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,025
From $1,235 taxes and fees incl.
Prefer another date?
Save up to 44%!
Winnipeg to Cancun
Sat, December 15, 2018 7 days All inclusive
Reg. $2,205
From $1,245 taxes and fees incl.
Prefer another date?
Save up to 44%!
Winnipeg to Riviera Maya
Mon, December 17, 2018 7 days All inclusive
Reg. $2,265
From $1,275 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 34%!
Winnipeg to Jamaica
Mon, January 28, 2019 7 days European Plan
Reg. $2,055
From $1,365 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 38%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,095
From $1,295 taxes and fees incl.
Prefer another date?
Save up to 52%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,755
From $1,315 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 30%!
Winnipeg to Riviera Nayarit
Sun, January 6, 2019 7 days All inclusive
Reg. $1,885
From $1,325 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 38%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,165
From $1,345 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Sat, December 15, 2018 7 days All inclusive
Reg. $2,225
From $1,355 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 32%!
Winnipeg to Cancun
Mon, January 21, 2019 7 days All inclusive
Reg. $1,995
From $1,355 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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