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 Orange Tree Golf Resort
Scottsdale, Arizona- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,920 ($209/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,200 ($314/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,271 ($610/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,838 ($977/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–19, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $935 ($312/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 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 16–29, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($304/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,637 ($546/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,802 ($467/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,925 ($1,561/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($331/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 17–20, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/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
- $7,492 ($1,070/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/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
- $5,911 ($844/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $4,054 ($290/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–31, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,650 ($189/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–31, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($80/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/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
- $1,673 ($239/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
- $2,153 ($308/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–24, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/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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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)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,642 ($274/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 17–23, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/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
- $4,276 ($611/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
- $5,748 ($821/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($80/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,957 ($994/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)