Winter Timeshare Rentals in Kissimmee

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23, 2026 – Jan 4, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,561 ($297/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 23, 2026 – Jan 1, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$1,764 ($196/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,118 ($303/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,268 ($159/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,180 ($236/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,003 ($167/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–31, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,136 ($162/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,118 ($303/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,874 ($312/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,365 ($228/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$870 ($174/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,734 ($217/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,362 ($295/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$870 ($174/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,365 ($228/night)

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Westgate Town Center

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,619 ($374/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$979 ($163/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 10
$2,314 ($331/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
$2,886 ($412/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,874 ($312/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,180 ($236/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$901 ($150/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 26, 2026 – Jan 9, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,825 ($273/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,804 ($225/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,101 ($157/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,299 ($162/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,440 ($305/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,242 ($207/night)

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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
$2,306 ($329/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,560 ($937/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,641 ($330/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$768 ($154/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,436 ($287/night)

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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
$2,696 ($385/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,061 ($294/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,524 ($218/night)

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Silver Lake Resort

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 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 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,768 ($253/night)

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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
$1,396 ($199/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,682 ($280/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,057 ($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)