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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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Viva Wyndham Fortuna Beach
Grand Bahama, Bahamas
Save up to 21%!
Toronto to Grand Bahama
Sat, February 29, 2020 7 days All inclusive
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Reg. $1,765
From $1,395 taxes and fees incl.
Prefer another date?
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Royalton White Sands Montego Bay
Jamaica
Save up to 42%!
Toronto to Jamaica
Wed, January 29, 2020 7 days All inclusive
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Reg. $2,925
From $1,685 taxes and fees incl.
Prefer another date?
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Riu Montego Bay
Jamaica
Save up to 37%!
Toronto to Jamaica
Sun, February 2, 2020 7 days All inclusive
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Reg. $2,705
From $1,705 taxes and fees incl.
Prefer another date?
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Riu Negril
Jamaica
Save up to 36%!
Toronto to Jamaica
Wed, January 29, 2020 7 days All inclusive
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Reg. $2,675
From $1,705 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Ocho Rios
Jamaica
Save up to 11%!
Toronto to Jamaica
Wed, January 29, 2020 7 days All inclusive
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Reg. $1,975
From $1,765 taxes and fees incl.
Prefer another date?
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Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 30%!
Toronto to St. Maarten
Sun, February 2, 2020 7 days All inclusive
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Reg. $2,415
From $1,695 taxes and fees incl.
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Riu Reggae
Jamaica
Save up to 6%!
Toronto to Jamaica
Fri, March 6, 2020 7 days All inclusive
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Reg. $2,015
From $1,895 taxes and fees incl.
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The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 28%!
Toronto to Antigua
Wed, January 29, 2020 7 days All inclusive
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Reg. $2,625
From $1,895 taxes and fees incl.
Prefer another date?
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Royalton Antigua Resort and Spa
Antigua, Antigua and Barbuda
Save up to 39%!
Toronto to Antigua
Wed, March 4, 2020 7 days All inclusive
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Reg. $3,655
From $2,235 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, March 7, 2020 7 days All inclusive
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Reg. $3,355
From $2,505 taxes and fees incl.
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