Winter Timeshare Rentals in Kissimmee

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Westgate Town Center

Kissimmee, Florida

Dec 4–11, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,022 ($432/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–9, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$499 ($166/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–9, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$639 ($213/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–9, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)

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Westgate Town Center

Kissimmee, Florida

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 16–21, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$679 ($136/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 16–21, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,312 ($262/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 16–21, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$946 ($189/night)

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Westgate Town Center

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,205 ($315/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–26, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,436 ($179/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–26, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,012 ($127/night)

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Westgate Town Center

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–26, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,943 ($243/night)

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Westgate Town Center

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 19–26, 2026 (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 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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

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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 - 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 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,198 ($171/night)

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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)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/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
$2,886 ($412/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$3,840 ($549/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–25, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$941 ($188/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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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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Westgate Town Center

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,110 ($159/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
$2,734 ($391/night)

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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 - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/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
$1,550 ($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
$1,476 ($211/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–25, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$759 ($152/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
$3,077 ($440/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–23, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$499 ($166/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–23, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/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
$1,878 ($268/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)
2 bed/2 bath, sleeps 8
$941 ($188/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)