Winter Timeshare Rentals in Greater Orlando

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,856 ($265/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,080 ($297/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–27, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,275 ($253/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–27, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,185 ($132/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–23, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,119 ($224/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–25, 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 18–24, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–31, 2026 (13 nights)
1 bed/1 bath, sleeps 4
$2,551 ($196/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–27, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$1,660 ($184/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–26, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,436 ($179/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–23, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$2,083 ($417/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–26, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,012 ($127/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 18–26, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,943 ($243/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–24, 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 18–23, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,506 ($301/night)

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Westgate Town Center

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,205 ($315/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–22, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$1,769 ($442/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–27, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,754 ($306/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–25, 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 18, 2026 – Jan 1, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$2,920 ($209/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 5
$4,725 ($675/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–22, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$941 ($235/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 18–24, 2026 (6 nights)
Studio/1 bath, sleeps 5
$3,871 ($645/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–23, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,506 ($301/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–22, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,268 ($317/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–30, 2026 (12 nights)
1 bed/1 bath, sleeps 4
$2,571 ($214/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–24, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,743 ($290/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–26, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,366 ($296/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–27, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$2,048 ($228/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–26, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$2,366 ($296/night)

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Westgate Town Center

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Westgate Town Center

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
4 bed/4 bath, sleeps 16
$2,257 ($322/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–26, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,760 ($220/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–22, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,268 ($317/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 18–24, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,349 ($391/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 18–27, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$2,754 ($306/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
$3,657 ($731/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–22, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$648 ($216/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$2,855 ($204/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–31, 2026 (12 nights)
1 bed/1 bath, sleeps 4
$2,458 ($205/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,641 ($377/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,240 ($463/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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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)