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 #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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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/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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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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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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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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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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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–31, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,304 ($130/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–31, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,022 ($202/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–31, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,240 ($224/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–31, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $950 ($95/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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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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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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WorldMark Indio
Indio, California- Dec 21–31, 2026 (10 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($242/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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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 21–27, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,458/night)
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Club Wyndham Atlanta
Atlanta, Georgia- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,795 ($256/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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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 #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
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,110 ($1,016/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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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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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,560 ($1,794/night)
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Holiday Inn Club Vacations Cape Canaveral Beach Resort
Cape Canaveral, Florida- Dec 21–24, 2026 (3 nights)
- 1 bed/1 bath, sleeps 6
- $929 ($310/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,057 ($211/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
- $10,271 ($1,467/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
- $12,450 ($1,779/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
- $8,090 ($1,156/night)
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Club Wyndham Atlanta
Atlanta, Georgia- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Dec 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($604/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
- $6,647 ($950/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
- $12,123 ($1,732/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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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($1,095/night)
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Hacienda del Mar Resort
Cabo San Lucas, Mexico- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $2,531 ($362/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 21–25, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $710 ($178/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
- $14,195 ($2,028/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 21, 2026 – Jan 1, 2027 (11 nights)
- 1 bed/2 bath, sleeps 4
- $6,620 ($602/night)
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The Westin Los Cabos Resort Villas - Baja Point
San Jose del Cabo, Mexico- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/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
- $9,339 ($1,334/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
- $12,609 ($1,801/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
- $9,072 ($1,296/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($496/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–24, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $247 ($82/night)