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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
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Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/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
- $2,205 ($441/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,177 ($363/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,930 ($704/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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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($147/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,734 ($248/night)
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Marriott Vacation Club Pulse, South Beach
Miami Beach, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- Studio/1 bath, sleeps 3
- $2,750 ($550/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $995 ($142/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,615 ($523/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($443/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,039 ($148/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($307/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $586 ($195/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $573 ($191/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $367 ($122/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($249/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,471 ($210/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,956 ($280/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $746 ($186/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,378 ($276/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,030 ($206/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,420 ($774/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 1, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,297 ($432/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 29, 2026 – Jan 2, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($824/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($662/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $3,295 ($824/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,909 ($477/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,466 ($293/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,101 ($220/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $773 ($155/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $697 ($232/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $773 ($258/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $3,055 ($764/night)