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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!
Starfish Jolly Beach Resort
Antigua, Antigua and Barbuda
Save up to 56%!
Toronto to Antigua
Fri, June 7, 2019 7 days All inclusive
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Reg. $2,285
From $995 taxes and fees incl.
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See our lowest price calendar
Jewel Paradise Cove Beach Resort And Spa
Jamaica
Save up to 37%!
Toronto to Jamaica
Wed, May 29, 2019 7 days All inclusive
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Reg. $1,845
From $1,155 taxes and fees incl.
Prefer another date?
See our lowest price calendar
Riu Montego Bay
Jamaica
Save up to 38%!
Toronto to Jamaica
Wed, May 29, 2019 7 days All inclusive
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Reg. $1,885
From $1,175 taxes and fees incl.
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Jewel Runaway Bay Beach and Golf Resort
Jamaica
Save up to 38%!
Toronto to Jamaica
Fri, May 17, 2019 7 days All inclusive
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Reg. $1,925
From $1,195 taxes and fees incl.
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Jewel Dunns River Beach Resort and Spa
Jamaica
Save up to 33%!
Toronto to Jamaica
Sun, June 9, 2019 7 days All inclusive
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Reg. $1,875
From $1,265 taxes and fees incl.
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Viva Wyndham Fortuna Beach
Grand Bahama, Bahamas
Save up to 35%!
Toronto to Grand Bahama
Sat, May 4, 2019 7 days All inclusive
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Reg. $1,845
From $1,205 taxes and fees incl.
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Riu Negril
Jamaica
Save up to 35%!
Toronto to Jamaica
Sun, June 9, 2019 7 days All inclusive
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Reg. $2,005
From $1,295 taxes and fees incl.
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Sonesta Maho Beach Resort Casino and Spa
St. Maarten, St Maarten
Save up to 27%!
Toronto to St. Maarten
Thu, May 9, 2019 7 days All inclusive
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Reg. $1,675
From $1,225 taxes and fees incl.
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The Verandah Resort and Spa
Antigua, Antigua and Barbuda
Save up to 38%!
Toronto to Antigua
Fri, May 10, 2019 7 days All inclusive
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Reg. $2,765
From $1,715 taxes and fees incl.
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Pineapple Beach Club
Antigua, Antigua and Barbuda
Save up to 43%!
Toronto to Antigua
Fri, June 7, 2019 7 days All inclusive
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Reg. $3,085
From $1,755 taxes and fees incl.
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Royalton Antigua Resort and Spa
Antigua, Antigua and Barbuda
Save up to 37%!
Toronto to Antigua
Fri, May 10, 2019 7 days All inclusive
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Reg. $3,005
From $1,885 taxes and fees incl.
Prefer another date?
See our lowest price calendar

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