Winter Timeshare Rentals in Disney World

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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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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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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 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 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,277 ($213/night)

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 Cypress Palms

Kissimmee, Florida

Dec 20–25, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$941 ($188/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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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,142 ($163/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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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 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,894 ($271/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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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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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
Studio/1 bath, sleeps 4
$2,013 ($503/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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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 20–26, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$666 ($111/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
Studio/1 bath, sleeps 5
$2,593 ($648/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$986 ($164/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$710 ($178/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,955 ($492/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
$2,924 ($418/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 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 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)

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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 21–29, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,647 ($206/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 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,352 ($270/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/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
$2,018 ($168/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–27, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,605 ($321/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 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 Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$499 ($100/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/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 21–26, 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)
2 bed/2 bath, sleeps 8
$1,330 ($266/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
$535 ($178/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
$959 ($240/night)