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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,978 ($283/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2026 (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 20–26, 2026 (6 nights)
- 3 bed/2 bath, sleeps 10
- $2,153 ($359/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 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 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,894 ($271/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,042 ($292/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–24, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–23, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,586 ($370/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,586 ($370/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–23, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $499 ($166/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–23, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,476 ($211/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 20–24, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,013 ($503/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,818 ($273/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,789 ($199/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20, 2026 – Jan 2, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,567 ($197/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,866 ($267/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,590 ($265/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–25, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/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
- $710 ($178/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 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 21–25, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,277 ($319/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–29, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,214 ($277/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–31, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,685 ($268/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (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 21–29, 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 21–24, 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 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 21–31, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,996 ($200/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,605 ($321/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($418/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–24, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($240/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,230 ($461/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–24, 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 21–24, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $959 ($320/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–28, 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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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 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 Cypress Palms
Kissimmee, Florida- Dec 22–25, 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 22–30, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,214 ($277/night)