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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!
Riu Negril
Jamaica
Save up to 33%!
Toronto to Jamaica
Fri, July 12, 2019 7 days All inclusive
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Reg. $2,135
From $1,435 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Jewel Paradise Cove Beach Resort And Spa
Jamaica
Save up to 32%!
Toronto to Jamaica
Fri, July 12, 2019 7 days All inclusive
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Reg. $2,115
From $1,445 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Montego Bay
Jamaica
Save up to 26%!
Toronto to Jamaica
Wed, August 7, 2019 7 days All inclusive
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Reg. $1,965
From $1,445 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Jewel Dunns River Beach Resort and Spa
Jamaica
Save up to 32%!
Toronto to Jamaica
Fri, July 12, 2019 7 days All inclusive
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Reg. $2,125
From $1,455 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Reggae
Jamaica
Save up to 33%!
Toronto to Jamaica
Fri, August 2, 2019 7 days All inclusive
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Reg. $2,295
From $1,545 taxes and fees incl.
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Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 11%!
Toronto to St. Maarten
Thu, August 8, 2019 7 days All inclusive
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Reg. $2,045
From $1,825 taxes and fees incl.
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Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 40%!
Toronto to Antigua
Fri, July 12, 2019 7 days All inclusive
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Reg. $3,145
From $1,895 taxes and fees incl.
Prefer another date?
See our lowest price calendar
The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 29%!
Toronto to Antigua
Fri, July 12, 2019 7 days All inclusive
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Reg. $2,725
From $1,935 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Royalton Antigua Resort and Spa
Antigua, Antigua and Barbuda
Save up to 24%!
Toronto to Antigua
Fri, July 5, 2019 7 days All inclusive
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Reg. $3,055
From $2,335 taxes and fees incl.
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