Winter Rentals in Kissimmee

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 21–28, 2025 (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 21–26, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$855 ($171/night)

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Vacation Villas at Fantasy World

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,110 ($159/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$999 ($143/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–29, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$887 ($127/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$999 ($200/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 23–28, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,220 ($244/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 23–27, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$555 ($139/night)

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Westgate Town Center

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

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Westgate Town Center

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,922 ($275/night)

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Westgate Town Center

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,905 ($272/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

Westgate Town Center

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Westgate Town Center

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 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 - North Village

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/1.5 bath, sleeps 8
$1,330 ($190/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,704 ($243/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
3 bed/3 bath, sleeps 11
$2,750 ($393/night)

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Mystic Dunes Resort & Golf Club

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$999 ($143/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 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 - East Village

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 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 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/1.5 bath, sleeps 8
$1,330 ($190/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Dec 27, 2025 – Jan 2, 2026 (6 nights)
3 bed/3 bath, sleeps 8
$2,423 ($404/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,704 ($243/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,497 ($214/night)

Westgate Vacation Villas

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,725 ($246/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,932 ($276/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$888 ($127/night)

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Westgate Vacation Villas

Kissimmee, Florida

Jan 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,411 ($202/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jan 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$722 ($103/night)

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Westgate Vacation Villas

Kissimmee, Florida

Jan 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$888 ($127/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jan 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,659 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jan 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Parkway International Resort

Kissimmee, Florida

Jan 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$771 ($110/night)

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Vacation Village at Parkway

Kissimmee, Florida

Jan 4–11, 2026 (7 nights)
2 bed/4 bath, sleeps 8
$1,110 ($159/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jan 4–11, 2026 (7 nights)
3 bed/2 bath, sleeps 12
$1,434 ($205/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jan 4–9, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,096 ($219/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jan 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Jan 16–20, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$976 ($244/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jan 30 – Feb 6, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,659 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Feb 1–8, 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 - East Village

Kissimmee, Florida

Feb 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,495 ($214/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Feb 13–20, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,749 ($393/night)