Winter Timeshare Rentals in Disney World

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,276 ($325/night)

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Boulder Ridge Villas at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 26–28, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,495 ($748/night)

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Marriott's Sabal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,696 ($385/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 9
$6,892 ($985/night)

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Disney's Riviera Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$6,510 ($930/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$13,105 ($1,872/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$4,688 ($670/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$932 ($186/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,216 ($203/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,066 ($152/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,625 ($271/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,222 ($317/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$866 ($144/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$4,688 ($670/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$999 ($200/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,242 ($248/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$4,688 ($670/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$3,295 ($471/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,632 ($326/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,632 ($326/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,303 ($329/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,476 ($211/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$5,440 ($777/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$2,743 ($549/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 27–31, 2026 (4 nights)
Studio/1 bath, sleeps 5
$3,478 ($870/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,632 ($326/night)

Sheraton Vistana Villages

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
4 bed/4 bath, sleeps 16
$6,560 ($937/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,186 ($455/night)

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Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$5,668 ($810/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$4,688 ($670/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,161 ($309/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,004 ($286/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$3,295 ($549/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$666 ($133/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$2,205 ($441/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,497 ($214/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
$733 ($147/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$746 ($186/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
$1,030 ($206/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
$1,956 ($280/night)