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 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)
- 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)
- 1 bed/1 bath, sleeps 4
- $427 ($107/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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,402 ($914/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/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
- $6,402 ($914/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
- $3,458 ($494/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
- $3,458 ($494/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
- $6,402 ($914/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 9–12, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $684 ($228/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)
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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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/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 Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 9–13, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 9–13, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $702 ($175/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 Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 9–20, 2026 (11 nights)
- 2 bed/2 bath, sleeps 8
- $10,816 ($983/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 9–12, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/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 9–23, 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 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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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 9–16, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $3,458 ($494/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
- $3,458 ($494/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
- $3,813 ($381/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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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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Club Wyndham Nashville
Nashville, Tennessee- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $479 ($120/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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Club Wyndham Nashville
Nashville, Tennessee- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $719 ($180/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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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 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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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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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 #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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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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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($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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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 10–14, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,327 ($582/night)