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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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 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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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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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,284 ($469/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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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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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 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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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 9–13, 2026 (4 nights)
- 3 bed/2 bath, sleeps 8
- $1,374 ($344/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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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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,313 ($330/night)
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Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,306 ($472/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $648 ($162/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–18, 2026 (8 nights)
- 3 bed/2 bath, sleeps 8
- $10,870 ($1,359/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $8,636 ($2,159/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–15, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($153/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–15, 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 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–14, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $995 ($249/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,929 ($704/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($280/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $675 ($169/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–14, 2026 (4 nights)
- 3 bed/2 bath, sleeps 8
- $1,339 ($335/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $535 ($178/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–13, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 10–13, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $808 ($269/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,295 ($259/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,061 ($723/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,202 ($315/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–15, 2026 (5 nights)
- 3 bed/2 bath, sleeps 8
- $1,585 ($317/night)
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Hilton Club, The Central at 5th New York
New York City, New York- Dec 11–14, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $2,654 ($885/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,521 ($904/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,550 ($221/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)