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 7–14, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($221/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($142/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 7–21, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $15,728 ($1,123/night)
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Hilton Grand Vacations on Paradise
Las Vegas, Nevada- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 7–10, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–13, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($153/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($824/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($142/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 8–12, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,612 ($403/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $555 ($139/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–12, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $870 ($218/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–12, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($107/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–17, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,224 ($136/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–17, 2026 (9 nights)
- 3 bed/2 bath, sleeps 10
- $1,917 ($213/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 8–15, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $2,750 ($393/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–15, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($221/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 8–15, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $2,750 ($393/night)
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Hyatt Residence Club at Park Hyatt Beaver Creek
Beaver Creek, Colorado- Dec 8–12, 2026 (4 nights)
- 3 bed/3 bath, sleeps 8
- $4,330 ($1,083/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–13, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
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Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Dec 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,714 ($245/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–17, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $906 ($101/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–11, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $367 ($122/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–13, 2026 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,180 ($236/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 8–11, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $559 ($186/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–19, 2026 (10 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($330/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–23, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,365 ($98/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–23, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,856 ($133/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 9–12, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $451 ($150/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 9–16, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,246 ($1,321/night)
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Marriott's Grand Chateau
Las Vegas, Nevada- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($756/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $648 ($162/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 9–13, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $995 ($249/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–23, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,711 ($194/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 9–23, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,199 ($229/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–13, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $2,045 ($511/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 9–16, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $2,750 ($393/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,154 ($288/night)
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The Manhattan Club
New York City, New York- Dec 9–12, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,824 ($608/night)