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 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,003 ($201/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,053 ($865/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,669 ($238/night)
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Holiday Inn Club Vacations at Desert Club Resort
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,654 ($236/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,748 ($583/night)
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Holiday Inn Club Vacations at Desert Club Resort
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,654 ($236/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,512 ($502/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,598 ($657/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,526 ($1,218/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 3–6, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $343 ($114/night)
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Club Wyndham Park City
Park City, Utah- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,595 ($719/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,104 ($221/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 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 3–7, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $995 ($249/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $415 ($138/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,647 ($1,092/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,213 ($745/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,242 ($248/night)
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Morritt's Tortuga Club
East End, Grand Cayman, Cayman Islands- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,070 ($296/night)
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Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,252 ($750/night)
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Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,252 ($750/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,824 ($689/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
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Hyatt Beach House Resort
Key West, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Marriott's Grand Chateau
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,835 ($548/night)
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Aspen Mountain Residences
Aspen, Colorado- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 2
- $3,262 ($544/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($1,313/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $960 ($137/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($322/night)
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Grand Timber Lodge
Breckenridge, Colorado- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Grand Timber Lodge
Breckenridge, Colorado- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,421 ($346/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,560 ($1,794/night)
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Maui Lea at Maui Hill
Kihei, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,421 ($346/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,884 ($983/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Marriott's Phuket Beach Club
Phuket, Thailand- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Westgate Las Vegas Resort & Casino
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Club Wyndham Avenue Plaza
New Orleans, Louisiana- Jan 3–6, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $415 ($138/night)
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Club Wyndham Avenue Plaza
New Orleans, Louisiana- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 2
- $367 ($122/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)