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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Marriott's Shadow Ridge - The Villages
Palm Desert, California- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–5, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($180/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
- $3,840 ($549/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
- $3,290 ($470/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/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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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,922 ($275/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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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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/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
- $3,649 ($521/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)
- 2 bed/2 bath, sleeps 8
- $7,763 ($1,109/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/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
- $3,622 ($517/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 1–2, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $613 ($613/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,893 ($699/night)
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Marriott's Grand Chateau
Las Vegas, Nevada- Jan 1–8, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,750 ($393/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,794 ($685/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
- $2,153 ($308/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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,339 ($1,068/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,944 ($563/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
- $4,565 ($652/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,104 ($443/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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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–9, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,974 ($247/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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,057 ($580/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 1–5, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $710 ($178/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
- $2,815 ($313/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 1–5, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $359 ($90/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 1–8, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,909 ($558/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,404/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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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/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 Villas at Disney's Grand Californian Hotel & Spa
Anaheim, California- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($1,153/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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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,560 ($937/night)
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Wyndham Vacation Resorts Royal Garden at Waikiki
Honolulu, Hawaii- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($496/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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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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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)