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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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 14–22, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $3,238 ($405/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($310/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 14–21, 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 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,711 ($673/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $922 ($231/night)
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Marriott's Summit Watch
Park City, Utah- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($660/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($144/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($280/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,976 ($997/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 14–19, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $1,932 ($386/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $675 ($169/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Club Wyndham National Harbor
National Harbor, Maryland- Jan 14–17, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $1,418 ($473/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($180/night)
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WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 14–24, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($275/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–18, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,304 ($326/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,045 ($1,006/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 15–24, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($148/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 15–19, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($987/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,970 ($424/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,726 ($532/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,692 ($813/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 15–24, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,725 ($192/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 15–18, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $876 ($292/night)
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Club Wyndham Austin
Austin, Texas- Jan 15–18, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $876 ($292/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,611 ($802/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,611 ($802/night)
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Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 15–18, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 15–22, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $16,811 ($2,402/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,728 ($961/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 15–18, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($170/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,368 ($338/night)