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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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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Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $2,161 ($309/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $826 ($275/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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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $586 ($195/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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Grand Timber Lodge
Breckenridge, Colorado- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,165 ($388/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 10–13, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/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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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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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–13, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($186/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
- $3,001 ($429/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($314/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/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 Bali Hai Villas
Princeville, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/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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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 Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/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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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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Club Wyndham National Harbor
National Harbor, Maryland- Dec 10–13, 2026 (3 nights)
- 3 bed/2 bath, sleeps 10
- $1,436 ($479/night)
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Club Wyndham National Harbor
National Harbor, Maryland- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $915 ($305/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,323 ($581/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)
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Club Wyndham National Harbor
National Harbor, Maryland- Dec 10–13, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $823 ($274/night)
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Club Wyndham National Harbor
National Harbor, Maryland- Dec 10–13, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $639 ($213/night)
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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)
- Studio/1 bath, sleeps 4
- $2,139 ($306/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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/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
- $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
- $4,167 ($595/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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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 10–20, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $4,374 ($437/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–14, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $424 ($141/night)
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Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,984 ($283/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,004 ($572/night)
DiamondHead Beach Resort
Fort Myers Beach, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,768 ($253/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 11–14, 2026 (3 nights)
- 3 bed/3 bath, sleeps 10
- $1,330 ($443/night)
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Club Wyndham Park City
Park City, Utah- Dec 11–14, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($662/night)