Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
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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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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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($191/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
- $3,840 ($549/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)
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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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)
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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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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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,529 ($218/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
- $799 ($114/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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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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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $790 ($198/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27–31, 2026 (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 27–30, 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 28, 2026 – Jan 9, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $2,044 ($170/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 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 Cypress Palms
Kissimmee, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $463 ($154/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 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 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 9, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,356 ($113/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 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)
- 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)
- 2 bed/2 bath, sleeps 8
- $990 ($198/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 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 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, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($105/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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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 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 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 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)
- 1 bed/1 bath, sleeps 4
- $733 ($105/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 Cypress Palms
Kissimmee, Florida- Dec 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($307/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 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 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 3, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($197/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 Cypress Palms
Kissimmee, Florida- Dec 29, 2026 – Jan 4, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $653 ($109/night)