Christmas Timeshare Rentals in Kissimmee

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

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)
1 bed/1 bath, sleeps 4
$1,003 ($167/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)

Westgate Vacation Villas

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 10
$3,284 ($469/night)

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Silver Lake Resort

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22, 2026 – Jan 2, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$2,379 ($216/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22, 2026 – Jan 2, 2027 (11 nights)
1 bed/1 bath, sleeps 4
$1,730 ($157/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22, 2026 – Jan 2, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$3,230 ($294/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/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
$2,314 ($331/night)

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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)

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 - 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 - 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 - East Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,390 ($341/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)

Verified & Protected

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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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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,057 ($211/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$768 ($154/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 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 - 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 - 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 - River Island

Kissimmee, Florida

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

Verified & Protected

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)

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 - East Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,383 ($340/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
$2,423 ($346/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
$2,423 ($346/night)

Verified & Protected

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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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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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)

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
$1,878 ($268/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)

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
$2,886 ($412/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
$7,432 ($1,062/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
$2,042 ($292/night)

Verified & Protected

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)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

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

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

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

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

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

Verified & Protected

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)

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)

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

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,136 ($162/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)