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- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,085 ($869/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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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 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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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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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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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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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
- $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
- $5,638 ($806/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 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/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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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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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,671 ($810/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($331/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,298 ($550/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,712 ($542/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,802 ($467/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,505 ($417/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 10–13, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,346 ($449/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–15, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $7,107 ($1,421/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,510 ($1,085/night)
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 Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 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 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,892 ($1,149/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/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)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 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 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,840 ($549/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,462 ($292/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($714/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,314 ($463/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,115 ($519/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($449/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 11–16, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,375 ($475/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 13–17, 2027 (4 nights)
- 3 bed/3 bath, sleeps 10
- $4,385 ($1,096/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–20, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $5,475 ($1,095/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 15–21, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,321 ($554/night)