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 Avenue Plaza
New Orleans, Louisiana- Jan 17–22, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,504 ($250/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,220 ($244/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jan 17–22, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($277/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–21, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($715/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–27, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $897 ($90/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,358 ($765/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Sheraton Desert Oasis
Scottsdale, Arizona- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,313 ($330/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,497 ($500/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,106 ($1,015/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
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Olympic Village Inn
Olympic Valley, California- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,505 ($358/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,412 ($630/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–27, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $1,839 ($184/night)
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Aspen Mountain Residences
Aspen, Colorado- Jan 17–23, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $671 ($96/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–22, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($550/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($332/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,929 ($704/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–22, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($692/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,647 ($1,092/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,733 ($533/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Garza Blanca Resort & Spa Los Cabos
Cabo San Lucas, Mexico- Jan 17–27, 2027 (10 nights)
- 1 bed/2 bath, sleeps 4
- $4,876 ($488/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,510 ($1,073/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/3 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 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,281 ($326/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,069 ($438/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,031 ($576/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,596 ($599/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 17–22, 2027 (5 nights)
- 3 bed/3.5 bath, sleeps 8
- $8,745 ($1,749/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–22, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,462 ($292/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,031 ($576/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,106 ($1,015/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,113 ($1,016/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,901 ($700/night)