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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

Save up to 38%!
Winnipeg to Holguin
Fri, February 28, 2020 7 days All inclusive
Reg. $1,825
From $1,125 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 44%!
Winnipeg to Puerto Plata
Thu, March 19, 2020 7 days All inclusive
Reg. $2,055
From $1,145 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 36%!
Winnipeg to Varadero
Tue, March 10, 2020 7 days All inclusive
Reg. $1,855
From $1,185 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 39%!
Winnipeg to Los Cabos
Thu, January 30, 2020 7 days All inclusive
Reg. $2,025
From $1,235 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 38%!
Winnipeg to Varadero
Tue, March 10, 2020 7 days All inclusive
Reg. $2,045
From $1,265 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 37%!
Winnipeg to Cayo Coco
Sat, February 29, 2020 7 days All inclusive
Reg. $2,185
From $1,375 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 34%!
Winnipeg to Riviera Nayarit
Sun, March 8, 2020 7 days All inclusive
Reg. $2,225
From $1,465 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 28%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, March 1, 2020 7 days All inclusive
Reg. $2,045
From $1,475 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 26%!
Winnipeg to Mazatlán
Fri, January 31, 2020 7 days All inclusive
Reg. $2,005
From $1,475 taxes and fees incl.
Prefer another date?
Save up to 34%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,265
From $1,485 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 36%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $2,385
From $1,515 taxes and fees incl.
Prefer another date?
Save up to 35%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,385
From $1,545 taxes and fees incl.
Prefer another date?
Save up to 22%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $2,005
From $1,555 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 12%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $1,795
From $1,575 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 24%!
Winnipeg to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,125
From $1,605 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 26%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, March 1, 2020 7 days All inclusive
Reg. $2,175
From $1,615 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 29%!
Winnipeg to Cancun
Mon, March 2, 2020 7 days All inclusive
Reg. $2,275
From $1,625 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 33%!
Winnipeg to Cancun
Mon, March 2, 2020 7 days All inclusive
Reg. $2,435
From $1,625 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 40%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,745
From $1,645 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 31%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,435
From $1,685 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 11%!
Winnipeg to Punta Cana
Wed, March 18, 2020 7 days All inclusive
Reg. $1,935
From $1,715 taxes and fees incl.
Prefer another date?
Huatulco, Mexico
Save up to 25%!
Winnipeg to Huatulco
Tue, February 4, 2020 7 days All inclusive
Reg. $2,305
From $1,725 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 24%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,265
From $1,725 taxes and fees incl.
Prefer another date?
Save up to 33%!
Winnipeg to Varadero
Sat, March 21, 2020 7 days All inclusive
Reg. $2,595
From $1,735 taxes and fees incl.
Prefer another date?
Save up to 38%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,805
From $1,745 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 33%!
Winnipeg to Riviera Nayarit
Fri, February 7, 2020 7 days All inclusive
Reg. $2,785
From $1,865 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 23%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $2,455
From $1,885 taxes and fees incl.
Prefer another date?
Save up to 36%!
Winnipeg to Jamaica
Mon, February 24, 2020 7 days All inclusive
Reg. $2,965
From $1,895 taxes and fees incl.
Prefer another date?
La Romana, Dominican Republic
Save up to 10%!
Winnipeg to La Romana
Wed, March 18, 2020 7 days All inclusive
Reg. $2,135
From $1,915 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 45%!
Winnipeg to Cayo Santa Maria
Fri, March 6, 2020 7 days All inclusive
Reg. $1,715
From $945 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 38%!
Winnipeg to Varadero
Tue, March 10, 2020 7 days All inclusive
Reg. $1,565
From $975 taxes and fees incl.
Prefer another date?
Save up to 40%!
Winnipeg to Varadero
Tue, March 10, 2020 7 days All inclusive
Reg. $1,635
From $975 taxes and fees incl.
Prefer another date?
Save up to 43%!
Winnipeg to Holguin
Fri, February 28, 2020 7 days All inclusive
Reg. $1,755
From $1,005 taxes and fees incl.
Prefer another date?
Save up to 43%!
Winnipeg to Holguin
Fri, February 28, 2020 7 days All inclusive
Reg. $1,755
From $1,005 taxes and fees incl.
Prefer another date?
Save up to 40%!
Winnipeg to Varadero
Tue, March 31, 2020 7 days All inclusive
Reg. $1,715
From $1,035 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 39%!
Winnipeg to Puerto Plata
Thu, March 19, 2020 7 days All inclusive
Reg. $1,725
From $1,055 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 37%!
Winnipeg to Varadero
Tue, March 10, 2020 7 days All inclusive
Reg. $1,685
From $1,055 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 43%!
Winnipeg to Cayo Coco
Sat, February 29, 2020 7 days All inclusive
Reg. $1,895
From $1,075 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 42%!
Winnipeg to Puerto Plata
Thu, March 19, 2020 7 days All inclusive
Reg. $1,895
From $1,105 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 30%!
Winnipeg to Varadero
Tue, March 31, 2020 7 days All inclusive
Reg. $1,585
From $1,105 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 39%!
Winnipeg to Puerto Vallarta
Fri, March 6, 2020 7 days All inclusive
Reg. $1,845
From $1,125 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 42%!
Winnipeg to Cayo Coco
Sat, February 29, 2020 7 days All inclusive
Reg. $1,925
From $1,125 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 41%!
Winnipeg to Cayo Coco
Sat, February 29, 2020 7 days All inclusive
Reg. $1,905
From $1,125 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 38%!
Winnipeg to Cayo Santa Maria
Fri, March 6, 2020 7 days All inclusive
Reg. $1,825
From $1,125 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 32%!
Winnipeg to Varadero
Tue, March 31, 2020 7 days All inclusive
Reg. $1,675
From $1,135 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 44%!
Winnipeg to Puerto Plata
Thu, March 19, 2020 7 days All inclusive
Reg. $2,055
From $1,145 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 30%!
Winnipeg to Mazatlán
Fri, January 31, 2020 7 days European Plan
Reg. $1,625
From $1,145 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 15%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $1,465
From $1,245 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 36%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, March 1, 2020 7 days All inclusive
Reg. $1,975
From $1,255 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 32%!
Winnipeg to Puerto Vallarta
Fri, January 31, 2020 7 days All inclusive
Reg. $1,855
From $1,265 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 56%!
Winnipeg to Los Cabos
Thu, January 30, 2020 7 days All inclusive
Reg. $2,875
From $1,265 taxes and fees incl.
Prefer another date?
La Romana, Dominican Republic
Save up to 14%!
Winnipeg to La Romana
Wed, March 4, 2020 7 days European Plan
Reg. $1,565
From $1,345 taxes and fees incl.
Prefer another date?
Santo Domingo, Dominican Republic
Save up to 14%!
Winnipeg to Santo Domingo
Wed, April 1, 2020 7 days All inclusive
Reg. $1,575
From $1,355 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 39%!
Winnipeg to Los Cabos
Thu, January 30, 2020 7 days All inclusive
Reg. $2,025
From $1,235 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 29%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $1,935
From $1,365 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 33%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,155
From $1,435 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 33%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $2,145
From $1,445 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 13%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $1,725
From $1,505 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 35%!
Winnipeg to Los Cabos
Thu, January 30, 2020 7 days All inclusive
Reg. $2,395
From $1,545 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 12%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $1,795
From $1,575 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 31%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $2,365
From $1,625 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 29%!
Winnipeg to Cancun
Mon, March 2, 2020 7 days All inclusive
Reg. $2,275
From $1,625 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 32%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $2,425
From $1,655 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 43%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $2,905
From $1,665 taxes and fees incl.
Prefer another date?
Save up to 44%!
Winnipeg to Jamaica
Mon, February 24, 2020 7 days All inclusive
Reg. $3,245
From $1,815 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 30%!
Winnipeg to Cancun
Mon, March 2, 2020 7 days All inclusive
Reg. $2,615
From $1,825 taxes and fees incl.
Prefer another date?
Save up to 42%!
Winnipeg to Jamaica
Mon, March 2, 2020 7 days All inclusive
Reg. $3,365
From $1,955 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 44%!
Winnipeg to Puerto Plata
Thu, March 19, 2020 7 days All inclusive
Reg. $1,725
From $965 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 30%!
Winnipeg to Mazatlán
Fri, January 31, 2020 7 days Breakfast Plan
Reg. $1,585
From $1,115 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 36%!
Winnipeg to Cayo Coco
Sat, February 29, 2020 7 days All inclusive
Reg. $1,755
From $1,125 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 15%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $1,465
From $1,245 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 39%!
Winnipeg to Los Cabos
Thu, January 30, 2020 7 days All inclusive
Reg. $2,025
From $1,235 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 27%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $1,825
From $1,335 taxes and fees incl.
Prefer another date?
Save up to 34%!
Winnipeg to Cancun
Mon, March 2, 2020 7 days All inclusive
Reg. $2,085
From $1,375 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 34%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,105
From $1,385 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 33%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $2,145
From $1,445 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 29%!
Winnipeg to Riviera Nayarit
Fri, January 31, 2020 7 days All inclusive
Reg. $2,025
From $1,435 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 33%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,155
From $1,435 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 13%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $1,725
From $1,505 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 51%!
Winnipeg to Puerto Vallarta
Fri, March 6, 2020 7 days All inclusive
Reg. $2,975
From $1,465 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 34%!
Winnipeg to Riviera Nayarit
Sun, March 8, 2020 7 days All inclusive
Reg. $2,225
From $1,465 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 26%!
Winnipeg to Mazatlán
Fri, January 31, 2020 7 days All inclusive
Reg. $2,005
From $1,475 taxes and fees incl.
Prefer another date?
Save up to 22%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $2,005
From $1,555 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 35%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,375
From $1,545 taxes and fees incl.
Prefer another date?
Save up to 35%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,385
From $1,545 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 35%!
Winnipeg to Los Cabos
Thu, January 30, 2020 7 days All inclusive
Reg. $2,395
From $1,545 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 31%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $2,365
From $1,625 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 35%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,425
From $1,575 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 34%!
Winnipeg to Cancun
Mon, March 2, 2020 7 days All inclusive
Reg. $2,375
From $1,575 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 32%!
Winnipeg to Punta Cana
Wed, April 1, 2020 7 days All inclusive
Reg. $2,425
From $1,655 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 24%!
Winnipeg to Riviera Maya
Mon, March 9, 2020 7 days All inclusive
Reg. $2,125
From $1,605 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 35%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,455
From $1,605 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 35%!
Winnipeg to Riviera Maya
Mon, March 2, 2020 7 days All inclusive
Reg. $2,455
From $1,605 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 40%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $2,795
From $1,665 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 43%!
Winnipeg to Punta Cana
Wed, March 4, 2020 7 days All inclusive
Reg. $2,905
From $1,665 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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