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 Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,818 ($1,117/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 24–29, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $295 ($59/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $577 ($115/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,944 ($1,421/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 24–27, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($808/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24 – Feb 1, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,446 ($306/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,554 ($511/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Marriott's Summit Watch
Park City, Utah- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($441/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,065 ($516/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 24–31, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $7,647 ($1,092/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,739 ($963/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($332/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,374 ($625/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24 – Feb 3, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $3,032 ($303/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,832 ($547/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,366 ($767/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,090 ($1,156/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $998 ($200/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24 – Feb 2, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $2,528 ($281/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($222/night)
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Playa Grande Resort & Grand Spa
Cabo San Lucas, Mexico- Jan 24–31, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,769 ($253/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 24–28, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($715/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24 – Feb 1, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,870 ($234/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24 – Feb 1, 2027 (8 nights)
- 3 bed/2 bath, sleeps 10
- $2,283 ($285/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–27, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $896 ($299/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($496/night)
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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Jan 24 – Feb 7, 2027 (14 nights)
- 3 bed/2 bath, sleeps 8
- $6,565 ($469/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24 – Feb 2, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $2,068 ($230/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 24–26, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,057 ($528/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 24–30, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $6,666 ($1,111/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 24–28, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($633/night)