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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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)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $7,655 ($1,094/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 Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,688 ($384/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,079 ($216/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
- $18,009 ($2,573/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 21, 2026 – Jan 4, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $6,620 ($473/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($768/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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WorldMark Seaside
Seaside, Oregon- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,818 ($260/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,277 ($213/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $986 ($164/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–25, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $959 ($240/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–25, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,565 ($938/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
- $17,137 ($2,448/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
- $13,541 ($1,934/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–29, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,647 ($206/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 21–26, 2026 (5 nights)
- 4 bed/4 bath, sleeps 12
- $9,181 ($1,836/night)
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Wyndham Kauai Coast Resort at the Beachboy
Kapaa, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,202 ($743/night)
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Hacienda del Mar Resort
Cabo San Lucas, Mexico- Dec 21–28, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,330 ($619/night)
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The Westin Resort & Spa, Cancun
Cancun, Mexico- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $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
- $3,404 ($486/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/night)
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WorldMark Indio
Indio, California- Dec 21–31, 2026 (10 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($242/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($1,094/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
- $14,026 ($2,004/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $759 ($152/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($188/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–27, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,743 ($290/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–25, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 5
- $11,252 ($2,250/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–27, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,295 ($216/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,743 ($290/night)
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Club Wyndham Austin
Austin, Texas- Dec 21–24, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,039 ($346/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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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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West 57th Street by Hilton Club
New York City, New York- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,358 ($872/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 Ocean Walk
Daytona Beach, Florida- Dec 21–29, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($276/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–31, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,996 ($200/night)