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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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The Christie Lodge
Avon, Colorado- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,002 ($143/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,145 ($592/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
- $3,230 ($461/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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/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 Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/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
- $5,557 ($794/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,123 ($303/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
- $2,804 ($401/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,821 ($403/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–6, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,220 ($305/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $739 ($246/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $4,493 ($642/night)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,797 ($828/night)
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Villa del Palmar Cabo San Lucas
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 6
- $6,892 ($985/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–5, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($166/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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The Cliffs at Princeville
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 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
- $4,984 ($712/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
- $5,748 ($821/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $9,726 ($1,389/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/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
- $5,816 ($831/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
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,565 ($652/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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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 2–6, 2027 (4 nights)
- 3 bed/2 bath, sleeps 8
- $1,150 ($287/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
- $6,892 ($985/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
- $5,099 ($728/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
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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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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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,800 ($1,257/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $12,560 ($1,794/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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Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $1,769 ($253/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–5, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $901 ($300/night)
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Royal Islander Club la Plage
St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,440 ($206/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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Grand Luxxe at Vidanta Riviera Maya
Playa del Carmen, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,794 ($542/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,099 ($728/night)
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The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)