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- Jan 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $852 ($170/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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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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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,304 ($326/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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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 Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 14–17, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($186/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
- $6,565 ($938/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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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($188/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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,271 ($318/night)
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Club Wyndham Resort at Avon
Avon, Colorado- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($688/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 Great Smokies Lodge
Sevierville, Tennessee- Jan 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($144/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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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 Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,276 ($255/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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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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,077 ($269/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 14–17, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($314/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 14–18, 2027 (4 nights)
- 3 bed/2 bath, sleeps 8
- $1,339 ($335/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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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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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
- $8,200 ($1,171/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
- $6,884 ($983/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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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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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($280/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($310/night)
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Villa del Palmar Cancun Luxury Beach Resort & Spa
Cancun, Mexico- Jan 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,186 ($455/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 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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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,726 ($532/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 15–23, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,484 ($311/night)
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Bluegreen's StreamSide at Vail
Vail, Colorado- Jan 15–18, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $2,260 ($753/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,412 ($202/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 15–18, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $973 ($324/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 15–19, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,271 ($318/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 15–19, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,077 ($269/night)