Winter Timeshare Rentals in Greater Orlando

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–17, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–19, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$613 ($123/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$977 ($140/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,830 ($261/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 15–17, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,895 ($948/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 15–19, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$741 ($185/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,392 ($199/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 15–19, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$1,128 ($282/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 15–19, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$535 ($134/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 16–20, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,021 ($255/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 16–20, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$746 ($186/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 16–21, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,260 ($252/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 16–21, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,821 ($364/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 16–21, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$924 ($185/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–23, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,620 ($270/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–20, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$906 ($302/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–23, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,778 ($296/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–21, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,145 ($286/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–24, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,374 ($196/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–23, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$950 ($158/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–22, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,383 ($277/night)

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Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

Dec 17–20, 2026 (3 nights)
Studio/1 bath, sleeps 4
$1,759 ($586/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–21, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$844 ($211/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 17–22, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,330 ($266/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–23, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,312 ($219/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–22, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,021 ($204/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,022 ($289/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,497 ($214/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 17–24, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,083 ($155/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–21, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$1,638 ($410/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 17–22, 2026 (5 nights)
Studio/1 bath, sleeps 4
$2,357 ($471/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–20, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$666 ($222/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–20, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$1,321 ($440/night)

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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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 17–23, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,198 ($200/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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WorldMark Orlando Kingstown Reef

Orlando, Florida

Dec 18–21, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$1,165 ($388/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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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 18–21, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$1,453 ($484/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 18–22, 2026 (4 nights)
Studio/1 bath, sleeps 4
$1,765 ($441/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 18–22, 2026 (4 nights)
Studio/1 bath, sleeps 4
$1,765 ($441/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 18–23, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,119 ($224/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 Cypress Palms

Kissimmee, Florida

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,107 ($158/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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Sheraton Vistana Resort

Orlando, Florida

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