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
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,600 ($1,086/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,866 ($267/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,482 ($414/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $2,314 ($331/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21, 2026 – Jan 4, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $25,203 ($1,800/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 21–27, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $5,470 ($912/night)
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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The Club at Solaz, Los Cabos
San Jose del Cabo, Mexico- Dec 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,764 ($395/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 21–26, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($506/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,233 ($1,748/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $21,824 ($3,118/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,104 ($1,872/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,230 ($461/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–24, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $959 ($320/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–24, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,560 ($1,794/night)
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Hilton Vacation Club Cabo Azul Los Cabos
San Jose del Cabo, Mexico- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,352 ($270/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–24, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $959 ($320/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $959 ($137/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,669 ($953/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 21–28, 2026 (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- Dec 21–24, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,777 ($1,825/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–24, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($240/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,995 ($1,856/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,458 ($208/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,664 ($238/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,628 ($1,090/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–29, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,214 ($277/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,983 ($1,140/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,981 ($1,140/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,605 ($321/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,066 ($1,013/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,015 ($1,716/night)
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WorldMark Seaside
Seaside, Oregon- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,818 ($260/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,323 ($1,903/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $924 ($185/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($418/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,617 ($1,088/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,800 ($1,257/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($550/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)