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 Cypress Palms
Kissimmee, Florida- Dec 23–26, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $499 ($166/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–26, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–28, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($224/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 23–28, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $3,851 ($770/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–29, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($127/night)
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WorldMark Orlando – Reunion
Kissimmee, Florida- Dec 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,641 ($377/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 23–28, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $3,851 ($770/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,506 ($301/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $2,313 ($578/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–29, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,462 ($244/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 23–29, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,079 ($180/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–26, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $875 ($292/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–26, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $875 ($292/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 24–28, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($633/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,506 ($301/night)
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Marriott's Royal Palms
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,039 ($434/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,030 ($343/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,030 ($343/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24, 2026 – Jan 4, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($202/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $764 ($255/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $737 ($105/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($141/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24, 2026 – Jan 4, 2027 (11 nights)
- 2 bed/2 bath, sleeps 8
- $3,170 ($288/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–29, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($496/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,962 ($1,280/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24, 2026 – Jan 2, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,545 ($283/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,717 ($245/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 24–26, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,123 ($562/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,423 ($808/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($266/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–29, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $755 ($151/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($234/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–29, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $577 ($115/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24, 2026 – Jan 2, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,869 ($208/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–28, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,268 ($317/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–28, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $941 ($235/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,096 ($299/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)