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 22–25, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,057 ($352/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 22–25, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $1,057 ($352/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
- $6,292 ($899/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 22–27, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,276 ($255/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,748 ($678/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 - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 22–29, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,058 ($580/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 22–27, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/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)
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
- $7,105 ($1,015/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 22–29, 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 22–29, 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 22–29, 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 23–28, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,396 ($279/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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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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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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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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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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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)
- Studio/1 bath, sleeps 4
- $3,513 ($502/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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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
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $12,015 ($1,716/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/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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Alexandra Resort and Spa
Grace Bay, Turks and Caicos Islands- Jan 23–30, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $6,701 ($957/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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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 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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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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–27, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $940 ($235/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 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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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,186 ($637/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,562 ($937/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)
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
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,328 ($1,047/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
- $3,568 ($510/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/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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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/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
- $1,141 ($228/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)