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 Ocean Walk
Daytona Beach, Florida- Jan 15–29, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,612 ($115/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,974 ($1,568/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,045 ($1,006/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 15–22, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,824 ($832/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,692 ($813/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 15–18, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,889 ($630/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 15–29, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($80/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,083 ($298/night)
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Grand Luxxe Spa Suites at Vidanta Riviera Maya
Playa del Carmen, Mexico- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,984 ($712/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,015 ($1,716/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 15–21, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,471 ($412/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 15–22, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $16,811 ($2,402/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 15–20, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $5,475 ($1,095/night)
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Club Wyndham Austin
Austin, Texas- Jan 15–18, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $876 ($292/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,268 ($467/night)
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Villas at Disneyland Hotel
Anaheim, California- Jan 15–17, 2027 (2 nights)
- Studio/1 bath, sleeps 2
- $932 ($466/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,726 ($532/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Jan 15–17, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $430 ($215/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,838 ($977/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 15–17, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $870 ($435/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 15–22, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $20,735 ($2,962/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,919 ($703/night)
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Westgate Park City Resort & Spa
Park City, Utah- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Club Wyndham Austin
Austin, Texas- Jan 15–18, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,383 ($461/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 15–19, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,255 ($564/night)