Winter Timeshare Rentals in Kissimmee

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,186 ($455/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (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 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,004 ($286/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,497 ($214/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,476 ($211/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,066 ($152/night)

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$999 ($200/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,039 ($148/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,471 ($210/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,378 ($276/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,030 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,956 ($280/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$733 ($147/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$995 ($249/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$746 ($186/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$535 ($134/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,466 ($293/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,101 ($220/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$773 ($155/night)

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Westgate Vacation Villas

Kissimmee, Florida

Jan 1–8, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,486 ($212/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–23, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$1,849 ($132/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–23, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,701 ($193/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–23, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,489 ($249/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 14–20, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,207 ($201/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 14–20, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$826 ($138/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 14–20, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,568 ($261/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 19–24, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,048 ($210/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 19–26, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$932 ($133/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 19–26, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,365 ($195/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 19–26, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,765 ($252/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 19–24, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,370 ($274/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 19–24, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$719 ($144/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 30 – Feb 6, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$932 ($133/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 30 – Feb 6, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,365 ($195/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 30 – Feb 6, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,765 ($252/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 6–20, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,894 ($207/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 6–20, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,857 ($276/night)

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Westgate Vacation Villas

Kissimmee, Florida

Feb 6–13, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,486 ($212/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 6–20, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$2,057 ($147/night)

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Westgate Town Center

Kissimmee, Florida

Feb 12–19, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,563 ($223/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 13–19, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,682 ($280/night)

Westgate Vacation Villas

Kissimmee, Florida

Feb 13–20, 2027 (7 nights)
2 bed/2 bath, sleeps 10
$2,423 ($346/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 13–19, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$901 ($150/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Feb 13–19, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,242 ($207/night)

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Westgate Town Center

Kissimmee, Florida

Feb 14–21, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,563 ($223/night)