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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 37%!
Toronto to Jamaica
Sat, September 21, 2019 7 days All inclusive
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Reg. $1,955
From $1,235 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Jewel Paradise Cove Beach Resort And Spa
Jamaica
Save up to 37%!
Toronto to Jamaica
Sat, September 21, 2019 7 days All inclusive
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Reg. $1,945
From $1,235 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Jewel Dunns River Beach Resort and Spa
Jamaica
Save up to 33%!
Toronto to Jamaica
Sat, September 14, 2019 7 days All inclusive
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Reg. $1,955
From $1,315 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Jewel Runaway Bay Beach and Golf Resort
Jamaica
Save up to 30%!
Toronto to Jamaica
Sat, September 14, 2019 7 days All inclusive
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Reg. $1,885
From $1,315 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Royalton White Sands Montego Bay
Jamaica
Save up to 39%!
Toronto to Jamaica
Sat, September 21, 2019 7 days All inclusive
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Reg. $2,215
From $1,345 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 20%!
Toronto to St. Maarten
Thu, September 5, 2019 7 days All inclusive
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Reg. $1,705
From $1,365 taxes and fees incl.
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See our lowest price calendar
The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 38%!
Toronto to Antigua
Fri, September 13, 2019 7 days All inclusive
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Reg. $2,165
From $1,345 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 14%!
Toronto to Antigua
Fri, September 13, 2019 7 days All inclusive
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Reg. $1,615
From $1,395 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Royalton Antigua Resort and Spa
Antigua, Antigua and Barbuda
Save up to 28%!
Toronto to Antigua
Fri, September 13, 2019 7 days All inclusive
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Reg. $2,785
From $1,995 taxes and fees incl.
Prefer another date?
See our lowest price calendar

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