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- Jan 8–11, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,057 ($352/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 9–15, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,150 ($358/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 9–11, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,135 ($568/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $935 ($312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–15, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $4,162 ($694/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($80/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $901 ($300/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,150 ($287/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,150 ($287/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($157/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($166/night)
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Marriott's Villas at Doral
Miami, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,232 ($308/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $940 ($235/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $739 ($246/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–15, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $693 ($115/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–15, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–15, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,145 ($191/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–15, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($195/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,309 ($330/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,766 ($681/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,085 ($869/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,179 ($740/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–23, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,280 ($306/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–23, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–23, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $4,054 ($290/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–23, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–23, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $4,054 ($290/night)
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Hyatt Beach House Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,914 ($416/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–16, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–14, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,379 ($595/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,183 ($312/night)