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 St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,508 ($1,358/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,380 ($1,483/night)
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The Point at Poipu
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,275 ($611/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 22–26, 2027 (4 nights)
- 2 bed/2.5 bath, sleeps 8
- $8,091 ($2,023/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,531 ($362/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 22–29, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $15,285 ($2,184/night)
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Marriott's Summit Watch
Park City, Utah- Jan 22–25, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($626/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 22–29, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,018 ($1,288/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/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)
- 1 bed/2 bath, sleeps 4
- $5,740 ($820/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
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/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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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/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)
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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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,151 ($1,164/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/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
- $8,745 ($1,249/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $10,380 ($1,483/night)
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Divi Dutch Village Beach Resort
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/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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Grand Lodge on Peak 7
Breckenridge, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Marriott's Grand Chateau
Las Vegas, Nevada- Jan 23–26, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($808/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,034 ($1,576/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,328 ($1,047/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
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,759 ($552/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
- $3,458 ($494/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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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)