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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,431 ($490/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–30, 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 23–30, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,175 ($739/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 23–30, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,494 ($642/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
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Westgate Las Vegas Resort & Casino
Las Vegas, Nevada- Jan 23–26, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,110 ($370/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–31, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,004 ($251/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–31, 2027 (8 nights)
- 3 bed/2 bath, sleeps 10
- $2,436 ($305/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–31, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,484 ($311/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–31, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,343 ($168/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 23 – Feb 6, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,920 ($209/night)
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Club Wyndham Resort at Avon
Avon, Colorado- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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The Ritz-Carlton Club, Lake Tahoe
Truckee, California- Jan 23–26, 2027 (3 nights)
- 3 bed/3.5 bath, sleeps 8
- $6,020 ($2,007/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 23–26, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $451 ($150/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
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The Ritz-Carlton Club, Aspen Highlands
Aspen, Colorado- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,996 ($1,857/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,701 ($957/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,914 ($416/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,832 ($547/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $6,020 ($860/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–29, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,731 ($533/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/night)
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The Westin Riverfront Mountain Villas
Avon, Colorado- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,801 ($829/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–29, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–29, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,963 ($423/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–29, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
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Royal Haciendas
Playa del Carmen, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,745 ($392/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 23–24, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $639 ($639/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,968 ($424/night)