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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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Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 33%!
Toronto to St. Maarten
Thu, November 19, 2020 7 days All inclusive
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Reg. $1,755
From $1,175 taxes and fees incl.
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Jewel Paradise Cove Beach Resort And Spa
Jamaica
Save up to 51%!
Toronto to Jamaica
Sat, October 24, 2020 7 days All inclusive
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Reg. $2,645
From $1,305 taxes and fees incl.
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Royalton White Sands Montego Bay
Jamaica
Save up to 43%!
Toronto to Jamaica
Sat, October 24, 2020 7 days All inclusive
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Reg. $2,295
From $1,315 taxes and fees incl.
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Riu Ocho Rios
Jamaica
Save up to 39%!
Toronto to Jamaica
Mon, November 9, 2020 7 days All inclusive
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Reg. $2,155
From $1,325 taxes and fees incl.
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Riu Negril
Jamaica
Save up to 32%!
Toronto to Jamaica
Mon, November 9, 2020 7 days All inclusive
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Reg. $1,945
From $1,325 taxes and fees incl.
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Riu Reggae
Jamaica
Save up to 34%!
Toronto to Jamaica
Sat, October 24, 2020 7 days All inclusive
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Reg. $2,035
From $1,335 taxes and fees incl.
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