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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Marriott's Harbour Lake
Orlando, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
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CHOOSE YOUR OWN DATES
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)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 3–10, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $8,200 ($1,171/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,594 ($319/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
- $9,398 ($1,343/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
- $5,257 ($751/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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,508 ($501/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,579 ($797/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,505 ($358/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/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
- $7,873 ($1,125/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
- $7,982 ($1,140/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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
- $7,872 ($1,125/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($636/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,321 ($332/night)
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Grand Timber Lodge
Breckenridge, Colorado- Jan 3–10, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $4,925 ($704/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/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)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Hilton Grand Vacations on the Boulevard
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($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)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 3–10, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $10,920 ($1,560/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 2
- $3,290 ($658/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,778 ($1,825/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $11,207 ($1,601/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 4–11, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $9,780 ($1,397/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 4–9, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,057 ($211/night)
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Villas at Disneyland Hotel
Anaheim, California- Jan 4–8, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,952 ($488/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 4–9, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 4–9, 2027 (5 nights)
- 3 bed/2 bath, sleeps 8
- $1,462 ($292/night)
Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 4–7, 2027 (3 nights)
- Studio/1 bath, sleeps 2
- $826 ($275/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,782 ($969/night)
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WorldMark Park City
Park City, Utah- Jan 4–11, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
Verified & Protected
Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 4–11, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)