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 4–8, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $951 ($238/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Dec 4–5, 2026 (1 night)
- Studio/1 bath, sleeps 4
- $511 ($511/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 4–8, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $613 ($153/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 4–7, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 4–8, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $888 ($222/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($142/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–14, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $999 ($111/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–19, 2026 (14 nights)
- 3 bed/2 bath, sleeps 10
- $3,087 ($220/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,804 ($401/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $4,498 ($643/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–9, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($107/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,614 ($373/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–9, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $555 ($139/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–19, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,507 ($108/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–8, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $451 ($150/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–10, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($100/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,600 ($514/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,551 ($650/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–8, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–8, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $586 ($195/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–8, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $826 ($275/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–8, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $684 ($228/night)
Shell Island Beach Club
Sanibel Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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The Galleon Resort
Key West, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–10, 2026 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,057 ($211/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–8, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($221/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,175 ($454/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–19, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,161 ($154/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($142/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–9, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $870 ($218/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 5–11, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,292 ($382/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,058 ($580/night)