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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,887 ($472/night)
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Sunburst Resort
Steamboat Springs, Colorado- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,434 ($205/night)
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Morritt's The Londoner
East End, Grand Cayman, Cayman Islands- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,053 ($579/night)
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The Westin Riverfront Mountain Villas
Avon, Colorado- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 2–6, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $555 ($139/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
- $5,748 ($821/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–16, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $8,647 ($618/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,660 ($237/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,764 ($1,109/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,963 ($1,280/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,214 ($1,031/night)
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Marriott's Grande Vista
Orlando, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $7,382 ($1,055/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,403 ($486/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
- $6,091 ($870/night)
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Novaispania Residences by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 4 bed/4.5 bath, sleeps 12
- $9,071 ($1,296/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
- $3,295 ($471/night)
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Club Wyndham Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,766 ($753/night)
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Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/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
- $8,527 ($1,218/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
- $2,641 ($377/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
- $5,938 ($848/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,706 ($387/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/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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Club Wyndham Sea Gardens
Pompano Beach, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,554 ($365/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,200 ($314/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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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,527 ($1,218/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
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 MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Dawn Beach Club
St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 2–9, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Barcelo Aruba
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,494 ($642/night)