Winter Timeshare Rentals in Disney World

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,462 ($244/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$759 ($127/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 2, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,310 ($289/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–31, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,743 ($290/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,384 ($626/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,079 ($180/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,167 ($595/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–28, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,030 ($343/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–28, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$764 ($255/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–30, 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 25, 2026 – Jan 2, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,695 ($212/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,922 ($275/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,405 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 4, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$2,546 ($283/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,641 ($377/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$986 ($164/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–30, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,114 ($279/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–30, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,290 ($470/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,590 ($265/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,731 ($533/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$4,380 ($626/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$4,494 ($642/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,180 ($197/night)

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Marriott's Imperial Palm Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/2 bath, sleeps 10
$4,140 ($591/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 5
$6,129 ($876/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,132 ($447/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$866 ($124/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,641 ($377/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,641 ($330/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–31, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,003 ($201/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,987 ($284/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,268 ($181/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$4,603 ($658/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,542 ($220/night)