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 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/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
- $7,110 ($1,016/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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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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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 3–5, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $733 ($366/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 3–4, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $285 ($285/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)
Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/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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Hyatt Sunset Harbor Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/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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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 3–4, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $541 ($541/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 3–8, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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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 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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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–7, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $804 ($201/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,859 ($620/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
- $892 ($149/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,748 ($583/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 8
- $1,003 ($201/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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/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 3–7, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $995 ($249/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 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 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
- $3,404 ($681/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–7, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–7, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $995 ($249/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 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 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/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
- $5,579 ($797/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($322/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 4–8, 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 4–11, 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 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 4–8, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $804 ($201/night)