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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 52%!
Toronto to Jamaica
Mon, November 25, 2019 7 days All inclusive
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Reg. $2,445
From $1,165 taxes and fees incl.
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Viva Wyndham Fortuna Beach
Grand Bahama, Bahamas
Save up to 28%!
Toronto to Grand Bahama
Sat, January 4, 2020 7 days All inclusive
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Reg. $1,595
From $1,155 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Negril
Jamaica
Save up to 49%!
Toronto to Jamaica
Mon, November 25, 2019 7 days All inclusive
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Reg. $2,505
From $1,275 taxes and fees incl.
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See our lowest price calendar
Riu Ocho Rios
Jamaica
Save up to 26%!
Toronto to Jamaica
Mon, November 25, 2019 7 days All inclusive
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Reg. $1,735
From $1,285 taxes and fees incl.
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See our lowest price calendar
Riu Reggae
Jamaica
Save up to 49%!
Toronto to Jamaica
Mon, November 25, 2019 7 days All inclusive
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Reg. $2,585
From $1,315 taxes and fees incl.
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Royalton White Sands Montego Bay
Jamaica
Save up to 50%!
Toronto to Jamaica
Mon, November 25, 2019 7 days All inclusive
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Reg. $2,625
From $1,325 taxes and fees incl.
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The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 8%!
Toronto to Antigua
Fri, December 6, 2019 8 days All inclusive
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Reg. $1,665
From $1,525 taxes and fees incl.
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Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 26%!
Toronto to St. Maarten
Thu, December 12, 2019 7 days All inclusive
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Reg. $2,195
From $1,615 taxes and fees incl.
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Royalton Antigua Resort and Spa
Antigua, Antigua and Barbuda
Save up to 22%!
Toronto to Antigua
Fri, November 29, 2019 7 days All inclusive
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Reg. $2,715
From $2,125 taxes and fees incl.
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Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 13%!
Toronto to Antigua
Sat, January 4, 2020 7 days All inclusive
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Reg. $2,765
From $2,405 taxes and fees incl.
Prefer another date?
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Royalton Saint Lucia Resort and Spa
St Lucia
Save up to 18%!
Toronto to St Lucia
Sat, January 4, 2020 7 days All inclusive
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Reg. $3,355
From $2,755 taxes and fees incl.
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Hideaway at Royalton Saint Lucia
St Lucia
Save up to 22%!
Toronto to St Lucia
Sat, January 4, 2020 7 days All inclusive
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Reg. $3,785
From $2,955 taxes and fees incl.
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