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 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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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/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
- $8,527 ($1,218/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
- $1,476 ($211/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
- $9,616 ($1,374/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
- $6,891 ($984/night)
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Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/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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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,524 ($218/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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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
- $9,180 ($1,311/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
- $8,417 ($1,202/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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Marriott's Harbour Lake
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,532 ($362/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
- $8,526 ($1,218/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 Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/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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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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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,202 ($172/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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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,628 ($375/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
- $8,527 ($1,218/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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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($80/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
- $5,284 ($755/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
- $523 ($105/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
- $817 ($163/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,295 ($185/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,145 ($191/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $937 ($187/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,554 ($213/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
- $733 ($105/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,048 ($171/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
- $990 ($198/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
- $1,136 ($162/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,295 ($259/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 3, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,923 ($275/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $415 ($138/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)