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 Riviera Resort
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($636/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,535 ($512/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 5
- $3,077 ($513/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,213 ($745/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,339 ($223/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 3–5, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $879 ($440/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,642 ($274/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $4,734 ($789/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,594 ($319/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,734 ($248/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,242 ($248/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Hyatt Beach House Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–7, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $804 ($201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $4,053 ($811/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $3,404 ($681/night)
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Club Wyndham Sea Gardens
Pompano Beach, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,982 ($330/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 4–16, 2027 (12 nights)
- 3 bed/2 bath, sleeps 10
- $3,413 ($284/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 4–16, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,794 ($233/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 4–16, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,869 ($156/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 4–16, 2027 (12 nights)
- 2 bed/2 bath, sleeps 6
- $3,413 ($284/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 4–16, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $2,794 ($233/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 4–8, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($660/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 5–11, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,693 ($449/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 5–11, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,693 ($449/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 5–10, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,935 ($387/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–18, 2027 (12 nights)
- 3 bed/2 bath, sleeps 10
- $3,565 ($297/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,492 ($498/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,060 ($612/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- 2 bed/2 bath, sleeps 9
- $9,276 ($1,855/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,651 ($530/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 6–11, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,466 ($693/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 6–12, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $4,494 ($749/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–18, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,928 ($244/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–18, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $2,928 ($244/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $702 ($100/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $950 ($136/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,647 ($235/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 6–18, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,961 ($163/night)