Winter Timeshare Rentals in Greater Orlando

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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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–23, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$719 ($240/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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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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Marriott's Grande Vista

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,513 ($502/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,397 ($171/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,590 ($265/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,112 ($222/night)

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Marriott's Grande Vista

Orlando, Florida

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

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,180 ($197/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,586 ($370/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 4
$3,138 ($523/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 9
$6,782 ($969/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–23, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 20–26, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$2,423 ($404/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,590 ($265/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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Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,968 ($424/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–23, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$959 ($320/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$2,641 ($440/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 1, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$2,345 ($195/night)

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Marriott's Harbour Lake

Orlando, Florida

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

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
Studio/1 bath, sleeps 4
$2,397 ($599/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,978 ($283/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–30, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$1,996 ($200/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,866 ($267/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
$2,886 ($412/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–25, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$710 ($178/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–27, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,743 ($290/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,330 ($266/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,924 ($418/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,352 ($270/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–29, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,647 ($206/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,352 ($270/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,003 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–25, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$959 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$719 ($240/night)