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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!
Save up to 26%!
Winnipeg to Holguin
Fri, January 3, 2020 7 days All inclusive
Reg. $1,685
From $1,245 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 34%!
Winnipeg to Puerto Plata
Thu, January 2, 2020 7 days All inclusive
Reg. $1,925
From $1,275 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 23%!
Winnipeg to Varadero
Tue, January 7, 2020 7 days All inclusive
Reg. $1,665
From $1,285 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 22%!
Winnipeg to Varadero
Tue, January 7, 2020 7 days All inclusive
Reg. $1,755
From $1,365 taxes and fees incl.
Prefer another date?
Save up to 46%!
Winnipeg to Punta Cana
Wed, January 22, 2020 7 days All inclusive
Reg. $2,755
From $1,475 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 27%!
Winnipeg to Cayo Coco
Sat, January 18, 2020 7 days All inclusive
Reg. $2,045
From $1,495 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 37%!
Winnipeg to Punta Cana
Wed, January 29, 2020 7 days All inclusive
Reg. $2,455
From $1,555 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 17%!
Winnipeg to Mazatlán
Fri, January 3, 2020 7 days All inclusive
Reg. $1,875
From $1,565 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 10%!
Winnipeg to Los Cabos
Wed, January 22, 2020 7 days All inclusive
Reg. $1,785
From $1,615 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 12%!
Winnipeg to Punta Cana
Wed, December 18, 2019 7 days All inclusive
Reg. $1,865
From $1,645 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 19%!
Winnipeg to Riviera Maya
Mon, January 6, 2020 7 days All inclusive
Reg. $2,055
From $1,665 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 32%!
Winnipeg to Punta Cana
Wed, January 8, 2020 7 days All inclusive
Reg. $2,475
From $1,695 taxes and fees incl.
Prefer another date?
Save up to 19%!
Winnipeg to Riviera Maya
Mon, January 20, 2020 7 days All inclusive
Reg. $2,115
From $1,715 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 19%!
Winnipeg to Riviera Maya
Mon, January 6, 2020 7 days All inclusive
Reg. $2,165
From $1,755 taxes and fees incl.
Prefer another date?
Ixtapa-Zihuatanejo, Mexico
Save up to 8%!
Winnipeg to Ixtapa-Zihuatanejo
Sun, January 19, 2020 7 days All inclusive
Reg. $1,925
From $1,765 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 11%!
Winnipeg to Punta Cana
Wed, December 18, 2019 7 days All inclusive
Reg. $2,015
From $1,795 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 16%!
Winnipeg to Cancun
Mon, January 20, 2020 7 days All inclusive
Reg. $2,135
From $1,795 taxes and fees incl.
Prefer another date?
Save up to 19%!
Winnipeg to Riviera Maya
Mon, January 20, 2020 7 days All inclusive
Reg. $2,235
From $1,815 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 20%!
Winnipeg to Riviera Maya
Mon, February 3, 2020 7 days All inclusive
Reg. $2,265
From $1,815 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 11%!
Winnipeg to Riviera Nayarit
Fri, January 3, 2020 7 days All inclusive
Reg. $2,045
From $1,825 taxes and fees incl.
Prefer another date?
Save up to 38%!
Winnipeg to Jamaica
Mon, January 6, 2020 7 days All inclusive
Reg. $3,085
From $1,905 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 42%!
Winnipeg to Varadero
Tue, November 12, 2019 7 days All inclusive
Reg. $1,385
From $805 taxes and fees incl.
Prefer another date?
Save up to 44%!
Winnipeg to Varadero
Tue, November 12, 2019 7 days All inclusive
Reg. $1,535
From $865 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 39%!
Winnipeg to Varadero
Tue, November 12, 2019 7 days All inclusive
Reg. $1,495
From $915 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 45%!
Winnipeg to Cayo Coco
Sat, December 14, 2019 7 days All inclusive
Reg. $1,655
From $915 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 42%!
Winnipeg to Cayo Coco
Sat, December 14, 2019 7 days All inclusive
Reg. $1,595
From $925 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 40%!
Winnipeg to Cayo Santa Maria
Fri, December 6, 2019 7 days All inclusive
Reg. $1,555
From $935 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 39%!
Winnipeg to Varadero
Tue, November 12, 2019 7 days All inclusive
Reg. $1,545
From $945 taxes and fees incl.
Prefer another date?
Save up to 17%!
Winnipeg to Varadero
Tue, December 3, 2019 7 days All inclusive
Reg. $1,135
From $945 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 45%!
Winnipeg to Cayo Santa Maria
Fri, December 6, 2019 7 days All inclusive
Reg. $1,755
From $965 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 18%!
Winnipeg to Punta Cana
Mon, November 18, 2019 7 days All inclusive
Reg. $1,225
From $1,005 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 36%!
Winnipeg to Cayo Coco
Sat, December 14, 2019 7 days All inclusive
Reg. $1,595
From $1,025 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 39%!
Winnipeg to Puerto Plata
Thu, January 2, 2020 7 days All inclusive
Reg. $1,685
From $1,035 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 36%!
Winnipeg to Varadero
Tue, November 12, 2019 7 days All inclusive
Reg. $1,645
From $1,055 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 31%!
Winnipeg to Mazatlán
Fri, December 13, 2019 7 days European Plan
Reg. $1,595
From $1,095 taxes and fees incl.
Prefer another date?
Save up to 30%!
Winnipeg to Holguin
Fri, January 3, 2020 7 days All inclusive
Reg. $1,575
From $1,105 taxes and fees incl.
Prefer another date?
Save up to 28%!
Winnipeg to Holguin
Fri, January 3, 2020 7 days All inclusive
Reg. $1,555
From $1,115 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 37%!
Winnipeg to Mazatlán
Fri, December 13, 2019 7 days All inclusive
Reg. $1,815
From $1,135 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 31%!
Winnipeg to Puerto Plata
Thu, January 9, 2020 7 days All inclusive
Reg. $1,685
From $1,155 taxes and fees incl.
Prefer another date?
Santo Domingo, Dominican Republic
Save up to 16%!
Winnipeg to Santo Domingo
Mon, November 11, 2019 7 days All inclusive
Reg. $1,375
From $1,155 taxes and fees incl.
Prefer another date?
La Romana, Dominican Republic
Save up to 15%!
Winnipeg to La Romana
Mon, December 9, 2019 7 days All inclusive
Reg. $1,445
From $1,225 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 40%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $1,815
From $1,085 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 39%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $1,895
From $1,165 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 16%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $1,405
From $1,185 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 15%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $1,465
From $1,245 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 43%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,275
From $1,295 taxes and fees incl.
Prefer another date?
Save up to 45%!
Winnipeg to Jamaica
Mon, December 9, 2019 7 days All inclusive
Reg. $2,355
From $1,305 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 36%!
Winnipeg to Cancun
Mon, November 11, 2019 7 days All inclusive
Reg. $2,055
From $1,315 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 36%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $2,095
From $1,345 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 36%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $2,115
From $1,345 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 25%!
Winnipeg to Los Cabos
Sun, December 8, 2019 7 days All inclusive
Reg. $1,805
From $1,355 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 39%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $2,285
From $1,385 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 33%!
Winnipeg to Cancun
Mon, November 11, 2019 7 days All inclusive
Reg. $2,285
From $1,525 taxes and fees incl.
Prefer another date?
Save up to 40%!
Winnipeg to Jamaica
Mon, December 16, 2019 7 days All inclusive
Reg. $2,555
From $1,545 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 18%!
Winnipeg to Los Cabos
Sun, December 8, 2019 7 days All inclusive
Reg. $2,055
From $1,675 taxes and fees incl.
Prefer another date?
Save up to 8%!
Winnipeg to Jamaica
Mon, December 9, 2019 7 days All inclusive
Reg. $1,955
From $1,795 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 18%!
Winnipeg to Punta Cana
Mon, November 18, 2019 7 days All inclusive
Reg. $1,225
From $1,005 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 39%!
Winnipeg to Cayo Coco
Sat, December 14, 2019 7 days All inclusive
Reg. $1,525
From $925 taxes and fees incl.
Prefer another date?
Puerto Plata, Dominican Republic
Save up to 39%!
Winnipeg to Puerto Plata
Thu, January 2, 2020 7 days All inclusive
Reg. $1,695
From $1,035 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 39%!
Winnipeg to Punta Cana
Mon, November 18, 2019 7 days All inclusive
Reg. $1,755
From $1,075 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 35%!
Winnipeg to Mazatlán
Fri, December 13, 2019 7 days Breakfast Plan
Reg. $1,585
From $1,035 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 39%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $1,895
From $1,165 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 42%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $1,935
From $1,115 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 16%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $1,405
From $1,185 taxes and fees incl.
Prefer another date?
Mazatlán, Mexico
Save up to 34%!
Winnipeg to Mazatlán
Fri, December 13, 2019 7 days All inclusive
Reg. $1,775
From $1,175 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $1,965
From $1,205 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 48%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,325
From $1,205 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 48%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,325
From $1,205 taxes and fees incl.
Prefer another date?
Save up to 45%!
Winnipeg to Jamaica
Mon, December 9, 2019 7 days All inclusive
Reg. $2,355
From $1,305 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 38%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,005
From $1,245 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 31%!
Winnipeg to Riviera Nayarit
Fri, November 8, 2019 7 days All inclusive
Reg. $1,815
From $1,255 taxes and fees incl.
Prefer another date?
Save up to 41%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,175
From $1,275 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 36%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $2,095
From $1,345 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 36%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $2,115
From $1,345 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 37%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,035
From $1,285 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 43%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,275
From $1,295 taxes and fees incl.
Prefer another date?
Riviera Nayarit, Mexico
Save up to 31%!
Winnipeg to Riviera Nayarit
Fri, November 29, 2019 7 days All inclusive
Reg. $1,915
From $1,315 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 36%!
Winnipeg to Cancun
Mon, November 11, 2019 7 days All inclusive
Reg. $2,055
From $1,315 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 39%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $2,285
From $1,385 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,175
From $1,325 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,165
From $1,325 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 14%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $1,615
From $1,395 taxes and fees incl.
Prefer another date?
Puerto Vallarta, Mexico
Save up to 42%!
Winnipeg to Puerto Vallarta
Fri, November 8, 2019 7 days All inclusive
Reg. $2,315
From $1,345 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 35%!
Winnipeg to Cancun
Mon, November 11, 2019 7 days All inclusive
Reg. $2,085
From $1,345 taxes and fees incl.
Prefer another date?
Save up to 54%!
Winnipeg to Cancun
Mon, November 11, 2019 7 days All inclusive
Reg. $2,945
From $1,345 taxes and fees incl.
Prefer another date?
Los Cabos, Mexico
Save up to 25%!
Winnipeg to Los Cabos
Sun, December 8, 2019 7 days All inclusive
Reg. $1,805
From $1,355 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 37%!
Winnipeg to Jamaica
Mon, December 9, 2019 7 days All inclusive
Reg. $2,285
From $1,435 taxes and fees incl.
Prefer another date?
Save up to 33%!
Winnipeg to Cancun
Mon, November 11, 2019 7 days All inclusive
Reg. $2,035
From $1,355 taxes and fees incl.
Prefer another date?
Save up to 30%!
Winnipeg to Riviera Maya
Mon, November 18, 2019 7 days All inclusive
Reg. $1,975
From $1,375 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 34%!
Winnipeg to Jamaica
Mon, December 9, 2019 7 days All inclusive
Reg. $2,215
From $1,465 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 39%!
Winnipeg to Riviera Maya
Mon, November 11, 2019 7 days All inclusive
Reg. $2,285
From $1,385 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 35%!
Winnipeg to Cancun
Mon, November 11, 2019 7 days All inclusive
Reg. $2,125
From $1,385 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 18%!
Winnipeg to Jamaica
Mon, December 9, 2019 7 days All inclusive
Reg. $1,825
From $1,495 taxes and fees incl.
Prefer another date?
Save up to 46%!
Winnipeg to Punta Cana
Wed, January 22, 2020 7 days All inclusive
Reg. $2,755
From $1,475 taxes and fees incl.
Prefer another date?
Punta Cana, Dominican Republic
Save up to 26%!
Winnipeg to Punta Cana
Mon, November 11, 2019 7 days All inclusive
Reg. $2,005
From $1,485 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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