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
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $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)
- 1 bed/1 bath, sleeps 4
- $3,181 ($454/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,284 ($469/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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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,505 ($358/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/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
- $9,835 ($1,405/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/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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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($159/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/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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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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,328 ($1,047/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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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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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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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,186 ($637/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 23–25, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,150 ($575/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($152/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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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 23–29, 2027 (6 nights)
- 2 bed/2.5 bath, sleeps 6
- $9,290 ($1,548/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
- $9,616 ($1,374/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
- $1,141 ($228/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)
- 3 bed/3 bath, sleeps 10
- $10,914 ($1,559/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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23 – Feb 6, 2027 (14 nights)
- 3 bed/3 bath, sleeps 12
- $24,986 ($1,785/night)
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Valdoro Mountain Lodge, a Hilton Grand Vacations Club
Breckenridge, Colorado- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($346/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
- $4,603 ($658/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,295 ($471/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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Mayan Palace at Vidanta Nuevo Vallarta
Nuevo Vallarta, Mexico- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,204 ($315/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
- $6,892 ($985/night)
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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Jan 23–30, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $2,914 ($416/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/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
- $3,497 ($500/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Club Wyndham Long Wharf
Newport, Rhode Island- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $839 ($120/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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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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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,282 ($183/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,925 ($1,561/night)