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- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,763 ($1,109/night)
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The Westin Riverfront Mountain Villas
Avon, Colorado- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $666 ($222/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,712 ($673/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,207 ($441/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,311 ($1,187/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,711 ($542/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,852 ($1,693/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($1,132/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 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 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,603 ($658/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,413 ($488/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,308 ($1,187/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,092 ($418/night)
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Hilton Grand Vacations Club Whistler
Whistler, British Columbia, Canada- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,380 ($626/night)
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The Point at Poipu
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,674 ($953/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,166 ($595/night)
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Marriott's Summit Watch
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,101 ($551/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,966/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,404/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,874 ($839/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,109 ($1,016/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($1,132/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $866 ($433/night)