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 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,308 ($1,187/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,923 ($275/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,136 ($162/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 5, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($105/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $16,375 ($2,339/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,741 ($1,249/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($195/night)
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Hilton Vacation Club Cabo Azul Los Cabos
San Jose del Cabo, Mexico- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,145 ($429/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,387 ($198/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $937 ($187/night)
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Club Wyndham Austin
Austin, Texas- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,746 ($392/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $415 ($83/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $577 ($115/night)
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The Club at Solaz, Los Cabos
San Jose del Cabo, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 3 bed/4 bath, sleeps 12
- $15,066 ($2,152/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,540 ($506/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28–31, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $955 ($191/night)
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Grand Luxxe Spa Suites at Vidanta Nuevo Vallarta
Nuevo Vallarta, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $7,437 ($1,062/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,145 ($191/night)
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Hacienda del Mar Resort
Cabo San Lucas, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $2,749 ($393/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($195/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($105/night)
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Marriott Vacation Club Pulse, South Beach
Miami Beach, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- Studio/1 bath, sleeps 3
- $2,750 ($550/night)
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Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,042 ($292/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,929 ($704/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,048 ($171/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $32,180 ($4,597/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $817 ($163/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $2,554 ($213/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 5, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,295 ($162/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($822/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($346/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 5, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,585 ($198/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $7,655 ($1,094/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $4,559 ($1,140/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 28, 2026 – Jan 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $959 ($240/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 28, 2026 – Jan 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,216 ($243/night)
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The Club at Solaz, Los Cabos
San Jose del Cabo, Mexico- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,366 ($624/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,942 ($1,849/night)
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Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Dec 28, 2026 – Jan 4, 2027 (7 nights)
- 6 bed/6 bath, sleeps 12
- $4,984 ($712/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 28, 2026 – Jan 9, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $1,356 ($113/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 2, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($190/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 29, 2026 – Jan 2, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,057 ($264/night)