Winter Timeshare Rentals in Disney World

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$499 ($100/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–25, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$959 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,352 ($270/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–27, 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 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,352 ($270/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
Studio/1 bath, sleeps 4
$3,077 ($769/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$719 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–28, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,743 ($290/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–28, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

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Holiday Inn Club Vacations Orlando Breeze Resort

Davenport, Florida

Dec 22–29, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$6,020 ($860/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 22–24, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,026 ($513/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–27, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,506 ($301/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–29, 2026 (7 nights)
3 bed/4 bath, sleeps 12
$13,105 ($1,872/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,505 ($358/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,647 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,192 ($149/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 22, 2026 – Jan 3, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,256 ($271/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–27, 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 22–31, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,821 ($202/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,114 ($279/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$535 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,054 ($264/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 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 22–25, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–27, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,119 ($224/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$2,641 ($377/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 23–26, 2026 (3 nights)
Studio/1 bath, sleeps 4
$1,830 ($610/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–26, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$875 ($292/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23, 2026 – Jan 2, 2027 (10 nights)
1 bed/1 bath, sleeps 4
$2,044 ($204/night)

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Disney's Riviera Resort

Lake Buena Vista, Florida

Dec 23–31, 2026 (8 nights)
Studio/1 bath, sleeps 5
$8,118 ($1,015/night)

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Hilton Grand Vacations at Tuscany Village

Orlando, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,268 ($317/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–28, 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 23–30, 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 23–27, 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 23, 2026 – Jan 1, 2027 (9 nights)
1 bed/1 bath, sleeps 4
$1,821 ($202/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–26, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$875 ($292/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–31, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,647 ($206/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–29, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 23–29, 2026 (6 nights)
Studio/1 bath, sleeps 5
$4,930 ($822/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)