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- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,212 ($303/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($1,014/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,110 ($1,016/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,560 ($1,794/night)
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The Point at Poipu
Koloa, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Marriott Vacation Club, New York City
New York City, New York- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 2
- $3,949 ($1,316/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,707 ($1,530/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $535 ($134/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $746 ($186/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,404/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,794 ($685/night)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Marriott's Grand Chateau
Las Vegas, Nevada- Jan 1–8, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,750 ($393/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,207 ($441/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,711 ($542/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,560 ($937/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/3 bath, sleeps 10
- $10,375 ($1,482/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($822/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 1–8, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,909 ($558/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $2,096 ($1,048/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,101 ($551/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,682 ($526/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–15, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–9, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,974 ($247/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,922 ($275/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 1–5, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $479 ($120/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,380 ($626/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,119 ($373/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,936 ($562/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,330 ($619/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–9, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,229 ($154/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)