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Book the tropical getaway you’ve been dreaming of for less with our Luxury Vacation Sale! Whether you’re planning a romantic escape for two or a family-friendly getaway, you can save big on the hottest luxury vacation packages. Plus, with our new Uplift Pay Monthly option, you can take price out of the equation with stress-free monthly payments. Deals won’t last long – book now to take advantage of these amazing luxury vacation savings.

Cayo Santa Maria, Cuba
Save up to 25%!
Windsor to Cayo Santa Maria
Tue, December 15, 2020 7 days All inclusive
Reg. $1,905
From $1,425 taxes and fees incl.
Prefer another date?
Save up to 22%!
Windsor to Varadero
Thu, December 3, 2020 7 days All inclusive
Reg. $1,995
From $1,565 taxes and fees incl.
Prefer another date?
Save up to 26%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,265
From $1,665 taxes and fees incl.
Prefer another date?
Save up to 24%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,315
From $1,755 taxes and fees incl.
Prefer another date?
Save up to 28%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $2,435
From $1,755 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 22%!
Windsor to Cancun
Mon, January 18, 2021 7 days All inclusive
Reg. $2,245
From $1,755 taxes and fees incl.
Prefer another date?
Cancun, Mexico
Save up to 23%!
Windsor to Cancun
Mon, January 18, 2021 7 days All inclusive
Reg. $2,355
From $1,805 taxes and fees incl.
Prefer another date?
Save up to 21%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,315
From $1,825 taxes and fees incl.
Prefer another date?
Save up to 28%!
Windsor to Riviera Maya
Mon, January 18, 2021 7 days All inclusive
Reg. $2,635
From $1,895 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 10%!
Windsor to Riviera Maya
Mon, December 14, 2020 7 days All inclusive
Reg. $2,135
From $1,915 taxes and fees incl.
Prefer another date?
Riviera Maya, Mexico
Save up to 6%!
Windsor to Riviera Maya
Mon, December 14, 2020 7 days All inclusive
Reg. $2,085
From $1,965 taxes and fees incl.
Prefer another date?
Save up to 24%!
Windsor to Jamaica
Sun, December 13, 2020 7 days All inclusive
Reg. $2,645
From $2,015 taxes and fees incl.
Prefer another date?
Save up to 10%!
Windsor to Riviera Maya
Mon, December 14, 2020 7 days All inclusive
Reg. $2,235
From $2,015 taxes and fees incl.
Prefer another date?

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