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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 39%!
Toronto to Antigua
Wed, December 19, 2018 7 days All inclusive
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Reg. $2,025
From $1,245 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Viva Wyndham Fortuna Beach
Grand Bahama, Bahamas
Save up to 22%!
Toronto to Grand Bahama
Sat, January 19, 2019 7 days All inclusive
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Reg. $1,735
From $1,355 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Montego Bay
Jamaica
Save up to 30%!
Toronto to Jamaica
Sun, January 6, 2019 7 days All inclusive
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Reg. $2,195
From $1,545 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Ocho Rios
Jamaica
Save up to 21%!
Toronto to Jamaica
Sun, January 6, 2019 7 days All inclusive
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Reg. $2,075
From $1,635 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Reggae
Jamaica
Save up to 9%!
Toronto to Jamaica
Sun, January 6, 2019 7 days All inclusive
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Reg. $1,845
From $1,685 taxes and fees incl.
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Riu Negril
Jamaica
Save up to 25%!
Toronto to Jamaica
Fri, January 11, 2019 7 days All inclusive
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Reg. $2,275
From $1,695 taxes and fees incl.
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Jewel Dunns River Beach Resort and Spa
Jamaica
Save up to 9%!
Toronto to Jamaica
Sun, January 6, 2019 7 days All inclusive
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Reg. $1,875
From $1,705 taxes and fees incl.
Prefer another date?
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The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 37%!
Toronto to Antigua
Wed, December 19, 2018 7 days All inclusive
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Reg. $3,365
From $2,115 taxes and fees incl.
Prefer another date?
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Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 19%!
Toronto to Antigua
Wed, January 2, 2019 7 days All inclusive
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Reg. $2,975
From $2,395 taxes and fees incl.
Prefer another date?
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Royalton Saint Lucia Resort and Spa
St Lucia
Save up to 9%!
Toronto to St Lucia
Sat, January 26, 2019 7 days All inclusive
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Reg. $3,095
From $2,805 taxes and fees incl.
Prefer another date?
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