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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 Montego Bay
Jamaica
Save up to 34%!
Toronto to Jamaica
Mon, October 28, 2019 7 days All inclusive
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Reg. $1,915
From $1,265 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Negril
Jamaica
Save up to 34%!
Toronto to Jamaica
Mon, October 28, 2019 7 days All inclusive
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Reg. $2,005
From $1,315 taxes and fees incl.
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See our lowest price calendar
Riu Ocho Rios
Jamaica
Save up to 5%!
Toronto to Jamaica
Mon, October 28, 2019 7 days All inclusive
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Reg. $1,405
From $1,335 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Royalton White Sands Montego Bay
Jamaica
Save up to 38%!
Toronto to Jamaica
Mon, October 28, 2019 7 days All inclusive
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Reg. $2,185
From $1,345 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Jewel Paradise Cove Beach Resort And Spa
Jamaica
Save up to 27%!
Toronto to Jamaica
Tue, October 8, 2019 7 days All inclusive
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Reg. $1,845
From $1,345 taxes and fees incl.
Prefer another date?
See our lowest price calendar
The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 12%!
Toronto to Antigua
Fri, October 4, 2019 7 days All inclusive
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Reg. $1,455
From $1,275 taxes and fees incl.
Prefer another date?
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Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 12%!
Toronto to Antigua
Fri, October 4, 2019 7 days All inclusive
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Reg. $1,505
From $1,325 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 22%!
Toronto to St. Maarten
Thu, October 3, 2019 7 days All inclusive
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Reg. $1,745
From $1,355 taxes and fees incl.
Prefer another date?
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Royalton Saint Lucia Resort and Spa
St Lucia
Save up to 25%!
Toronto to St Lucia
Sat, October 26, 2019 7 days All inclusive
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Reg. $2,335
From $1,755 taxes and fees incl.
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Royalton Antigua Resort and Spa
Antigua, Antigua and Barbuda
Save up to 31%!
Toronto to Antigua
Fri, October 4, 2019 7 days All inclusive
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Reg. $2,995
From $2,065 taxes and fees incl.
Prefer another date?
See our lowest price calendar

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