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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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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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24, 2026 – Jan 3, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,358 ($236/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 2
- $2,491 ($830/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,118 ($303/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
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,001 ($429/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 Cypress Palms
Kissimmee, Florida- Dec 24–30, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,874 ($312/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–30, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($167/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24, 2026 – Jan 3, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,515 ($151/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24, 2026 – Jan 3, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,658 ($266/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–30, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($228/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
- $13,759 ($1,966/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
- $1,660 ($553/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/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
- $1,878 ($626/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24, 2026 – Jan 3, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,163 ($116/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $431 ($144/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $527 ($176/night)
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Marriott's Royal Palms
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $790 ($263/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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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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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,136 ($162/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($314/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,802 ($543/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
- $4,069 ($581/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 25–28, 2026 (3 nights)
- 1 bed/2 bath, sleeps 5
- $4,276 ($1,425/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25–31, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,874 ($312/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
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,042 ($292/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,764 ($538/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($418/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25–30, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,180 ($236/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25–30, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $870 ($174/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 25–30, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,629 ($326/night)
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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
- $3,622 ($517/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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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
- $3,840 ($549/night)
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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
- $3,186 ($455/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $5,420 ($774/night)
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Sheraton Vistana Villages
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,772 ($396/night)
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Club Wyndham Santa Barbara
Pompano Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,724 ($246/night)