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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Sheraton Vistana Resort
Orlando, Florida- Dec 28–31, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($443/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,420 ($774/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 1, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,297 ($432/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 29, 2026 – Jan 2, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $599 ($150/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 29, 2026 – Jan 2, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,132 ($283/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 29, 2026 – Jan 2, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($824/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $697 ($232/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $3,295 ($824/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $988 ($247/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $639 ($160/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $773 ($155/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,117 ($279/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($662/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 30, 2026 – Jan 3, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,909 ($477/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 30, 2026 – Jan 2, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $773 ($258/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,466 ($293/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,651 ($663/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 9, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,240 ($249/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,419 ($605/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,707 ($1,530/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $764 ($191/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,116 ($279/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,627 ($542/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,748 ($583/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $2,111 ($704/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 5, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $4,184 ($837/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,730 ($683/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 9, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,519 ($169/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 5, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,965 ($593/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,743 ($549/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,712 ($542/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $866 ($433/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–7, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($164/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $684 ($342/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,936 ($562/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–10, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,336 ($260/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,119 ($373/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Westgate Vacation Villas
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/night)
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Marriott's Royal Palms
Orlando, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,306 ($329/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–5, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,458 ($614/night)