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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Wyndham St. Thomas, a Margaritaville Vacation Club Resort
East End, St. Thomas (USVI)- Jan 22–29, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $4,290 ($613/night)
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Bantry Bay
Bantry Bay, South Africa, Africa- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,968 ($424/night)
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Marriott's Summit Watch
Park City, Utah- Jan 22–25, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($626/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,963 ($1,280/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 22–29, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,535 ($219/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,512 ($502/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 22–29, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,018 ($1,288/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,579 ($1,083/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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WorldMark Scottsdale
Scottsdale, Arizona- Jan 23 – Feb 20, 2027 (28 nights)
- 1 bed/1 bath, sleeps 4
- $5,793 ($207/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–28, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,185 ($237/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–28, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $924 ($185/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,914 ($416/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,733 ($533/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,141 ($228/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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,731 ($533/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–28, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $626 ($125/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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The Ritz-Carlton Club, Aspen Highlands
Aspen, Colorado- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,996 ($1,857/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 23–24, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $639 ($639/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,405 ($486/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,153 ($450/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 23–30, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,494 ($642/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,968 ($424/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 23–30, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $923 ($132/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–27, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $940 ($235/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,328 ($1,047/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 23–29, 2027 (6 nights)
- 2 bed/2.5 bath, sleeps 6
- $9,290 ($1,548/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/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 MountainSide at Park City
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,290 ($756/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–28, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,141 ($228/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,354 ($193/night)
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Playa Grande Resort & Grand Spa
Cabo San Lucas, Mexico- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,658 ($237/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,749 ($250/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,963 ($423/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23–27, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $940 ($235/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,451 ($493/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 23 – Feb 2, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,399 ($240/night)