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 Ocean Walk
Daytona Beach, Florida- Jan 2–16, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,612 ($115/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,345 ($469/night)
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,117 ($874/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,192 ($548/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,192 ($548/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,469 ($496/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,327 ($332/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,647 ($329/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,604 ($321/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,920 ($1,560/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,920 ($1,560/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,693 ($385/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 2–4, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,334 ($667/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,802 ($543/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
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The Point at Poipu
Koloa, Hawaii- Jan 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($731/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Sunburst Resort
Steamboat Springs, Colorado- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,544 ($221/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,711 ($194/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–16, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,650 ($189/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 2–16, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($80/night)
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Royal Haciendas
Playa del Carmen, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,586 ($370/night)
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,014 ($504/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,007 ($601/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,126 ($1,304/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,109 ($1,016/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,901 ($700/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,559 ($520/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $12,015 ($1,716/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $875 ($292/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,731 ($533/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,312 ($187/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,172 ($391/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,782 ($969/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)