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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Hilton Grand Vacations Club Whistler
Whistler, British Columbia, Canada- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–10, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,568 ($174/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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,711 ($542/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,207 ($441/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,146 ($1,164/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 1–4, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,832 ($547/night)
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The Villas at Disney's Grand Californian Hotel & Spa
Anaheim, California- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $3,622 ($1,207/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,207 ($441/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($822/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,380 ($626/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,679 ($668/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–4, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $906 ($302/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/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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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($2,465/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,330 ($619/night)
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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–4, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($195/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–4, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $1,057 ($352/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–15, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–4, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $973 ($324/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 1–5, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $1,554 ($389/night)
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Westgate Flamingo Bay
Las Vegas, Nevada- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,087 ($155/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–9, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,229 ($154/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/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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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 1–15, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,764 ($555/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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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–10, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $2,833 ($315/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–15, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,280 ($306/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–15, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $4,054 ($290/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($1,075/night)
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WorldMark Midway
Midway, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–7, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,860 ($310/night)