Winter Timeshare Rentals in Disney World

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 9, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,554 ($213/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$990 ($198/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$415 ($138/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 9, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,048 ($171/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,330 ($443/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28–31, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$535 ($178/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$463 ($154/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$710 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,163 ($194/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 9, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$2,044 ($170/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$626 ($104/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,387 ($198/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,136 ($162/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 5, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$839 ($105/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28–31, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$733 ($105/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 9, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$1,356 ($113/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 5, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,295 ($162/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 5, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,585 ($198/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$817 ($163/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$523 ($105/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,220 ($244/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
Studio/1 bath, sleeps 4
$2,615 ($523/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$937 ($187/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,295 ($185/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$653 ($109/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 2, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$759 ($190/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,119 ($186/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 6, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,383 ($173/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,238 ($206/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 1, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$1,297 ($432/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,251 ($179/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,003 ($167/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 6, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,207 ($172/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$870 ($174/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,088 ($218/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 2, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$582 ($194/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 30, 2026 – Jan 2, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$1,987 ($662/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$941 ($188/night)

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The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 3, 2027 (4 nights)
Studio/1 bath, sleeps 5
$3,073 ($768/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 3, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$808 ($202/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 5, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,074 ($179/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 3, 2027 (4 nights)
Studio/1 bath, sleeps 4
$1,909 ($477/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 3, 2027 (4 nights)
Studio/1 bath, sleeps 5
$3,055 ($764/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 3, 2027 (3 nights)
Studio/1 bath, sleeps 4
$1,627 ($542/night)

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Boulder Ridge Villas at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 3, 2027 (3 nights)
Studio/1 bath, sleeps 5
$2,111 ($704/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 6, 2027 (6 nights)
Studio/1 bath, sleeps 4
$2,585 ($431/night)