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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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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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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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
- $6,560 ($937/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
- $1,277 ($213/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, 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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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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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 Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 4, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($196/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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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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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,185 ($455/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($237/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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $4,800 ($800/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
- $1,660 ($237/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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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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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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Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,276 ($325/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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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/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
- $3,188 ($455/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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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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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 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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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 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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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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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 Imperial Palm Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $4,112 ($588/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 4, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,158 ($270/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,043 ($174/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,326 ($221/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $693 ($115/night)
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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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 Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $888 ($178/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)
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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)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,198 ($240/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)
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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)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($724/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)