Winter Timeshare Rentals in Greater Orlando

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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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Marriott's Harbour Lake

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,711 ($387/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

Marriott's Grande Vista

Orlando, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
3 bed/3 bath, sleeps 12
$8,745 ($625/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,602 ($289/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,866 ($267/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 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 19–28, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,935 ($215/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 4
$1,705 ($341/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
$1,550 ($221/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,016 ($603/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
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,978 ($283/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 19–20, 2026 (1 night)
Studio/1 bath, sleeps 4
$415 ($415/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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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 4
$1,778 ($356/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,110 ($222/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$3,213 ($357/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,660 ($237/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 19–21, 2026 (2 nights)
Studio/1 bath, sleeps 4
$746 ($373/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/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
$1,476 ($211/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 2, 2027 (13 nights)
2 bed/2 bath, sleeps 8
$3,487 ($268/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 2, 2027 (13 nights)
1 bed/1 bath, sleeps 4
$2,567 ($197/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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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,482 ($414/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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Westgate Lakes Resort & Spa

Orlando, Florida

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

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 6
$2,153 ($359/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 5
$3,557 ($593/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 5
$4,640 ($773/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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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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/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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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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$2,711 ($387/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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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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
3 bed/2 bath, sleeps 10
$2,153 ($359/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
Studio/1 bath, sleeps 4
$1,497 ($374/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
$1,550 ($221/night)