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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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 Austin
Austin, Texas- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,257 ($564/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 9–15, 2026 (6 nights)
- 3 bed/2 bath, sleeps 8
- $1,207 ($201/night)
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Club Wyndham Austin
Austin, Texas- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,699 ($425/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 9–15, 2026 (6 nights)
- 3 bed/3 bath, sleeps 8
- $5,748 ($958/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 9–13, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,769 ($442/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 9–23, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,488 ($106/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 9–13, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,374 ($344/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 9–23, 2026 (14 nights)
- 3 bed/2 bath, sleeps 8
- $2,711 ($194/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 9–19, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($820/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 SeaWatch Resort
Myrtle Beach, South Carolina- Dec 9–15, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($111/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 SeaWatch Resort
Myrtle Beach, South Carolina- Dec 9–15, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $986 ($164/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 9–23, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,222 ($159/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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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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–19, 2026 (10 nights)
- Studio/1 bath, sleeps 2
- $2,941 ($294/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 9–13, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($442/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/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
- $4,930 ($704/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,914 ($583/night)
Grand Timber Lodge
Breckenridge, Colorado- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $929 ($310/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 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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La Cabana Beach Resort
Oranjestad, Aruba- Dec 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,042 ($292/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–16, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $906 ($151/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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,139 ($306/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
- $4,598 ($657/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
- $4,794 ($685/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,550 ($221/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $852 ($170/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
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La Cabana Beach Resort
Oranjestad, Aruba- Dec 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,042 ($292/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,128 ($226/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)
- Studio/1 bath, sleeps 4
- $2,306 ($329/night)
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Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $2,205 ($315/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)
The Westin Riverfront Mountain Villas
Avon, Colorado- Dec 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,069 ($438/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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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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
- $4,167 ($595/night)