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- Jan 9–12, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $901 ($300/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,650 ($1,093/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,150 ($287/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,150 ($287/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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The Ritz-Carlton Club, Aspen Highlands
Aspen, Colorado- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,996 ($1,857/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,898 ($1,557/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $7,382 ($1,055/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,692 ($385/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,252 ($750/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($157/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $10,920 ($1,560/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,866 ($267/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,343 ($192/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($166/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Marriott's Villas at Doral
Miami, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $940 ($235/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,085 ($869/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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The Cliff Club at Snowbird
Snowbird, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/3 bath, sleeps 10
- $10,924 ($1,561/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,192 ($313/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9 – Feb 6, 2027 (28 nights)
- 3 bed/2.5 bath, sleeps 8
- $26,883 ($960/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,179 ($740/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–15, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($195/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–15, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,145 ($191/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–15, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,219 ($1,031/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,859 ($408/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $3,268 ($467/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,403 ($486/night)
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The Ritz-Carlton Club, Aspen Highlands
Aspen, Colorado- Jan 9–16, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $10,870 ($1,553/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,929 ($704/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)