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 22–28, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($164/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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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,824 ($832/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 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)
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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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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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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/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 MountainSide at Park City
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,290 ($756/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,977 ($711/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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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,186 ($637/night)
Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/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
- $4,930 ($704/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 23–29, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,230 ($538/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
- $5,786 ($827/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 23–29, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,150 ($358/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/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
- $5,039 ($720/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,528 ($306/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–27, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,232 ($308/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,676 ($525/night)
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WorldMark Scottsdale
Scottsdale, Arizona- Jan 23 – Feb 20, 2027 (28 nights)
- 1 bed/1 bath, sleeps 4
- $5,849 ($209/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/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
- $5,366 ($767/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/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
- $4,603 ($658/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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,746 ($249/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,179 ($436/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,521 ($360/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 6
- $2,039 ($291/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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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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 23–30, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/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
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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–27, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,150 ($287/night)
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Caribbean Palm Village
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($253/night)