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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 16–23, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,449 ($350/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,219 ($1,031/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–20, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–20, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 16–20, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 16–21, 2026 (5 nights)
- 2 bed/3 bath, sleeps 8
- $3,568 ($714/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,277 ($182/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 16, 2026 – Jan 2, 2027 (17 nights)
- 3 bed/3.5 bath, sleeps 10
- $8,734 ($514/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,513 ($502/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 16, 2026 – Jan 2, 2027 (17 nights)
- 3 bed/3.5 bath, sleeps 10
- $8,745 ($514/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,413 ($1,202/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $2,222 ($159/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $4,498 ($643/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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La Cabana Beach Resort
Oranjestad, Aruba- Dec 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,374 ($196/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,580 ($369/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($266/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,833 ($202/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($265/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,856 ($265/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 17–20, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,554 ($518/night)
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Club Ocho Cascadas
Puerto Vallarta, Mexico- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 17–22, 2026 (5 nights)
- Studio/1 bath, sleeps 2
- $2,271 ($454/night)
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Club Wyndham Austin
Austin, Texas- Dec 17–31, 2026 (14 nights)
- Studio/1 bath, sleeps 4
- $3,553 ($254/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Dec 17–28, 2026 (11 nights)
- 1 bed/1 bath, sleeps 4
- $2,190 ($199/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Club Wyndham Austin
Austin, Texas- Dec 17–31, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $4,359 ($311/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 17–31, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,365 ($98/night)
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Club Wyndham Austin
Austin, Texas- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $5,667 ($405/night)
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Club Wyndham Austin
Austin, Texas- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,821 ($559/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $4,126 ($589/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 17–21, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $2,615 ($654/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 17–22, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,357 ($471/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 17–21, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,917 ($479/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $999 ($143/night)
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Club Wyndham Austin
Austin, Texas- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,795 ($256/night)
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Club Wyndham Austin
Austin, Texas- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
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Club Wyndham Austin
Austin, Texas- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,053 ($722/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $13,050 ($1,864/night)
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Costa Linda Beach Resort
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,162 ($595/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Falcon Point
Avon, Colorado- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)