Winter Timeshare Rentals in Kissimmee

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–23, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$639 ($213/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,612 ($373/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$759 ($152/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$499 ($100/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)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 2, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$1,356 ($113/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$941 ($188/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 2, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,018 ($168/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 2, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,584 ($215/night)

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

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,054 ($264/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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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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WorldMark Orlando – Reunion

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$2,641 ($377/night)

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 23–27, 2026 (4 nights)
Studio/1 bath, sleeps 5
$999 ($250/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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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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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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 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$986 ($164/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
$2,096 ($299/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
$866 ($124/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
$666 ($111/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,128 ($226/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
$1,268 ($181/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
$1,660 ($237/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$586 ($117/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 9, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,493 ($178/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 9, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,217 ($230/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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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 - 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
$1,440 ($206/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
$1,277 ($213/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$852 ($170/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
$1,524 ($218/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27–31, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$427 ($107/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27–31, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$626 ($157/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,326 ($221/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27–31, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$790 ($198/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
$1,476 ($211/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$693 ($115/night)