Christmas Timeshare Rentals in Kissimmee

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Vacation Village at Parkway

Kissimmee, Florida

Dec 21, 2025 – Jan 4, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,096 ($150/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,527 ($218/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,583 ($226/night)

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Westgate Town Center

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 19–27, 2025 (8 nights)
2 bed/2 bath, sleeps 8
$1,987 ($248/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–26, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$1,264 ($211/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,205 ($315/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,088 ($155/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,110 ($159/night)

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Star Island Resort

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
3 bed/3 bath, sleeps 8
$3,295 ($471/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$999 ($143/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,687 ($241/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$666 ($95/night)

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Vacation Villas at Fantasy World

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,932 ($276/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–29, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$887 ($127/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 23–28, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,220 ($244/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 23–27, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$555 ($139/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Hilton Vacation Club Aqua Sol Orlando West

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
3 bed/3 bath, sleeps 10
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 19–27, 2025 (8 nights)
2 bed/2 bath, sleeps 8
$1,987 ($248/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$999 ($143/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/1.5 bath, sleeps 8
$1,220 ($174/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–26, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$855 ($171/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
3 bed/3 bath, sleeps 8
$1,987 ($284/night)

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Hilton Vacation Club Aqua Sol Orlando West

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
3 bed/3 bath, sleeps 10
$2,200 ($314/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,768 ($253/night)

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Silver Lake Resort

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,358 ($194/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$999 ($200/night)

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Vacation Villas at Fantasy World

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,088 ($155/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$955 ($136/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Westgate Town Center

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,434 ($205/night)

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Westgate Town Center

Kissimmee, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$555 ($79/night)