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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!

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Royalton White Sands Montego Bay
Jamaica
Save up to 53%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
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Reg. $2,605
From $1,225 taxes and fees incl.
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Riu Ocho Rios
Jamaica
Save up to 33%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
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Reg. $2,135
From $1,425 taxes and fees incl.
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Riu Montego Bay
Jamaica
Save up to 35%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
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Reg. $2,235
From $1,455 taxes and fees incl.
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Riu Negril
Jamaica
Save up to 37%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
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Reg. $2,345
From $1,475 taxes and fees incl.
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Royalton Negril Resort and Spa
Jamaica
Save up to 49%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
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Reg. $3,045
From $1,555 taxes and fees incl.
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Royalton Antigua Resort and Spa
Antigua, Antigua and Barbuda
Save up to 41%!
Toronto to Antigua
Sat, February 20, 2021 7 days All inclusive
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Reg. $3,645
From $2,165 taxes and fees incl.
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The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 39%!
Toronto to Antigua
Sat, February 20, 2021 7 days All inclusive
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Reg. $3,745
From $2,275 taxes and fees incl.
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Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 36%!
Toronto to Antigua
Sat, February 20, 2021 7 days All inclusive
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Reg. $3,675
From $2,335 taxes and fees incl.
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Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 8%!
Toronto to St. Maarten
Thu, February 18, 2021 7 days All inclusive
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Reg. $2,655
From $2,435 taxes and fees incl.
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