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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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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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–6, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $367 ($122/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 #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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $746 ($249/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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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–6, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $535 ($178/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($496/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 3–10, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,565 ($938/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
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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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–8, 2027 (5 nights)
- 3 bed/2 bath, sleeps 8
- $1,242 ($248/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $888 ($178/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/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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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,001 ($429/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,157 ($165/night)
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Club Wyndham Sea Gardens
Pompano Beach, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,982 ($330/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,734 ($248/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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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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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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–11, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $5,859 ($732/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $577 ($115/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/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
- $5,906 ($844/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,178 ($436/night)
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Hilton Vacation Club Cabo Azul Los Cabos
San Jose del Cabo, Mexico- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 5
- $3,077 ($513/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $12,765 ($1,824/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 3–6, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $483 ($161/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/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
- $9,288 ($1,327/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 3–6, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $463 ($154/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $3,404 ($681/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 3–8, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,036 ($407/night)
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Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($724/night)
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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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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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,568 ($510/night)
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The Westin Riverfront Mountain Villas
Avon, Colorado- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)