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
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,146 ($1,164/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,852 ($1,693/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
Marriott's Crystal Shores
Marco Island, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 1–15, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,764 ($555/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
- $6,674 ($953/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/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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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($1,075/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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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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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/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
- $3,622 ($517/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–15, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,280 ($306/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $866 ($433/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,312 ($187/night)
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The Point at Poipu
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/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
- $5,874 ($839/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–7, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,860 ($310/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 Ocean Pointe
Palm Beach Shores, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,944 ($563/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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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
- $7,110 ($1,016/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
- $10,707 ($1,530/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–10, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $2,833 ($315/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–10, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,815 ($313/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 1–5, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $1,554 ($389/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 #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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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/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
- $6,838 ($977/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,057 ($580/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($2,465/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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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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,966/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($1,139/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 1–4, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–15, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $4,054 ($290/night)
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Westgate Vacation Villas
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/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)