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Christmas Timeshare Rentals

Christmas Timeshare Rentals

Celebrated each year on December 25, Christmas is the time for family traditions and festive travel. With schools and many businesses closed between Christmas Eve and New Year’s Day, the holiday season is perfect for a getaway - whether you’re dreaming of a snowy winter wonderland at a ski resort or a sunny beach Christmas with your loved ones!

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,042 ($292/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 22, 2026 – Jan 3, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,256 ($271/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–27, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,436 ($179/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–27, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,012 ($127/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–27, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,943 ($243/night)

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,886 ($412/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$759 ($127/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,462 ($244/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,079 ($180/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,432 ($1,062/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–26, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$499 ($166/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–26, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–26, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$639 ($213/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–29, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,462 ($244/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–29, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,079 ($180/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–29, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$759 ($127/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,397 ($171/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,112 ($222/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,247 ($232/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$1,699 ($121/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,462 ($176/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,586 ($370/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$946 ($189/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,312 ($262/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$679 ($136/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,476 ($211/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,605 ($321/night)