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Vacations from Windsor

Enjoy convenient flights departing from Windsor to top destinations across the Caribbean, Mexico and Central America. For our neighbouring Americans, you'll be pleased to know you can pay for your vacation in Canadian dollars!

New taxes and fees now included in pricing!
Starfish Jolly Beach Resort
Antigua, Antigua and Barbuda
Save up to 25%!
Toronto to Antigua
Wed, April 3, 2019 7 days All inclusive
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Reg. $1,795
From $1,345 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Viva Wyndham Fortuna Beach
Grand Bahama, Bahamas
Save up to 17%!
Toronto to Grand Bahama
Sat, March 30, 2019 7 days All inclusive
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Reg. $1,735
From $1,445 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Montego Bay
Jamaica
Save up to 33%!
Toronto to Jamaica
Sat, March 16, 2019 7 days All inclusive
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Reg. $2,385
From $1,595 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Ocho Rios
Jamaica
Save up to 22%!
Toronto to Jamaica
Fri, March 1, 2019 7 days All inclusive
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Reg. $2,195
From $1,715 taxes and fees incl.
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See our lowest price calendar
Royalton White Sands Montego Bay
Jamaica
Save up to 37%!
Toronto to Jamaica
Fri, March 1, 2019 7 days All inclusive
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Reg. $2,725
From $1,725 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Negril
Jamaica
Save up to 22%!
Toronto to Jamaica
Fri, April 5, 2019 7 days All inclusive
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Reg. $2,235
From $1,745 taxes and fees incl.
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Jewel Paradise Cove Beach Resort And Spa
Jamaica
Save up to 21%!
Toronto to Jamaica
Fri, April 5, 2019 7 days All inclusive
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Reg. $2,205
From $1,745 taxes and fees incl.
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See our lowest price calendar
Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 7%!
Toronto to St. Maarten
Thu, March 21, 2019 7 days All inclusive
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Reg. $2,165
From $2,015 taxes and fees incl.
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The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 35%!
Toronto to Antigua
Wed, March 20, 2019 7 days All inclusive
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Reg. $3,245
From $2,105 taxes and fees incl.
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Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 31%!
Toronto to Antigua
Wed, April 3, 2019 7 days All inclusive
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Reg. $3,465
From $2,395 taxes and fees incl.
Prefer another date?
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Hideaway at Royalton Saint Lucia
St Lucia
Save up to 17%!
Toronto to St Lucia
Sat, March 23, 2019 7 days All inclusive
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Reg. $3,335
From $2,765 taxes and fees incl.
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Royalton Saint Lucia Resort and Spa
St Lucia
Save up to 13%!
Toronto to St Lucia
Sat, March 16, 2019 7 days All inclusive
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Reg. $3,375
From $2,945 taxes and fees incl.
Prefer another date?
See our lowest price calendar

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