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 - 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 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($124/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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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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Marriott's Royal Palms
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/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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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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Marriott's Imperial Palm Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $3,835 ($548/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,629 ($204/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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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 Villages
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,665 ($238/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
- $2,859 ($408/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,542 ($220/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26–29, 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 26–30, 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 26, 2026 – Jan 2, 2027 (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 26, 2026 – Jan 4, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($196/night)
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Sheraton Vistana Villages
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,069 ($438/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26–31, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 9, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,493 ($178/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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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 9, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,217 ($230/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,253 ($282/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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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/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 1, 2027 (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 26, 2026 – Jan 1, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,180 ($197/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,590 ($265/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
- $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
- $3,786 ($541/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26–29, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $648 ($216/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 Lakeshore Reserve
Orlando, Florida- Dec 26–30, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,532 ($633/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
- $1,782 ($255/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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $4,603 ($767/night)
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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
- $1,550 ($221/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 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,114 ($186/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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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 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 27–31, 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)