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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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,977 ($711/night)
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Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,282 ($183/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,758 ($460/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($477/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,379 ($476/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 24–26, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $981 ($491/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,905 ($318/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,327 ($582/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 24–25, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $429 ($429/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 24–27, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,148 ($383/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/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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Westgate Park City Resort & Spa
Park City, Utah- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/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
- $4,112 ($588/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 24–31, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/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)
Playa Grande Resort & Grand Spa
Cabo San Lucas, Mexico- Jan 24–31, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,665 ($238/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,093 ($299/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,986 ($284/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 24 – Feb 5, 2027 (12 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($656/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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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 24–29, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/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
- $1,098 ($220/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
- $8,200 ($1,171/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($107/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $799 ($160/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($200/night)
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 24–31, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,516 ($1,502/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 24–30, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,339 ($223/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–30, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 24–29, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,069 ($414/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
- $1,339 ($223/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,948 ($790/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 24–29, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,003 ($201/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Jan 24–28, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($551/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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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 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)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 24–29, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $3,850 ($770/night)