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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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 15–19, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,255 ($564/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
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Club Wyndham Austin
Austin, Texas- Jan 15–18, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,030 ($343/night)
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Novaispania Residences by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 4 bed/4.5 bath, sleeps 12
- $9,071 ($1,296/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,630 ($661/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,537 ($220/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,494 ($642/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,949 ($564/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–19, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,200 ($314/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–30, 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 16–30, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $4,054 ($290/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 16–23, 2027 (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- Jan 16–19, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $935 ($312/night)
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Wyndham Reef Resort
East End, Grand Cayman, Cayman Islands- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 16–22, 2027 (6 nights)
- 1 bed/1 bath, sleeps 6
- $2,314 ($386/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 9
- $5,910 ($844/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–22, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $4,598 ($766/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,650 ($1,093/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,802 ($829/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,039 ($720/night)
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WorldMark Big Bear
Big Bear Lake, California- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,873 ($268/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,290 ($1,327/night)
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Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,740 ($820/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,908 ($701/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,712 ($673/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 16–23, 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 16–20, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($157/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–20, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,150 ($287/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,200 ($314/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $9,290 ($1,327/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,978 ($141/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 16–30, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,199 ($229/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 16–30, 2027 (14 nights)
- 3 bed/2 bath, sleeps 8
- $4,054 ($290/night)
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Westgate Park City Resort & Spa
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)