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 19–31, 2026 (12 nights)
- 1 bed/1 bath, sleeps 4
- $2,458 ($205/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 19–23, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $3,670 ($917/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 19–22, 2026 (3 nights)
- Studio/1 bath, sleeps 5
- $2,161 ($720/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,366 ($296/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,866 ($267/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Dec 19–24, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $4,191 ($838/night)
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Parc Soleil by Hilton Grand Vacations
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,453 ($779/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–26, 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 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $875 ($292/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Dec 20–21, 2026 (1 night)
- Studio/1 bath, sleeps 4
- $341 ($341/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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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)
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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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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Dec 20–22, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $952 ($476/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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Marriott's Harbour Lake
Orlando, Florida- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($404/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($188/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,590 ($265/night)
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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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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 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 20–23, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $959 ($320/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,138 ($523/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
- $1,180 ($197/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($164/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $759 ($152/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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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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Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($159/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 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,277 ($213/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,745 ($392/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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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,878 ($268/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($432/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
- $1,550 ($221/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,142 ($163/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($111/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
- $3,290 ($470/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($440/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20, 2026 – Jan 1, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $2,345 ($195/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 20–23, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($240/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
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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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,390 ($341/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
- $959 ($240/night)