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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Vacation Village at Parkway

Kissimmee, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–15, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$852 ($170/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–15, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$586 ($117/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–15, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,128 ($226/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$719 ($180/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$977 ($244/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,144 ($229/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–15, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,119 ($160/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,427 ($204/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$595 ($119/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$862 ($172/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
$1,440 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$977 ($140/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,392 ($199/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,830 ($261/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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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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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 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,136 ($162/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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Club Wyndham Cypress Palms

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
$2,968 ($424/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
$3,077 ($440/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 - West Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/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
$2,423 ($346/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,118 ($303/night)

Verified & Protected

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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–22, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$941 ($314/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 - East Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$3,513 ($502/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–22, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$507 ($169/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–22, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$684 ($228/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 - 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 - North Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,745 ($392/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 - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,042 ($292/night)

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/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
$2,772 ($396/night)

Verified & Protected

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)

Verified & Protected

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)

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
$3,022 ($432/night)