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 Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($221/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,403 ($486/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–11, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($831/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,600 ($514/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,384 ($626/night)
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Four Seasons Residence Club Aviara
Carlsbad, California- Dec 5–12, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
Hyatt Windward Pointe Resort
Key West, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $4,498 ($643/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,275 ($325/night)
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The Westin Mission Hills Villas
Rancho Mirage, California- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,358 ($194/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–19, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $7,327 ($523/night)
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Divi Dutch Village Beach Resort
Oranjestad, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($354/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,347 ($907/night)
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Coral Sands Resort
George Town, Grand Cayman, Cayman Islands- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($253/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,370 ($481/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
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Villa del Palmar Cabo San Lucas
Cabo San Lucas, Mexico- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $2,505 ($358/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 6–12, 2026 (6 nights)
- 1 bed/2 bath, sleeps 6
- $1,549 ($258/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $573 ($95/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,732 ($962/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 6–11, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,605 ($321/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,380 ($1,483/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
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Marriott's Phuket Beach Club
Phuket, Thailand- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,894 ($556/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Dec 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $944 ($189/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 6–11, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $415 ($83/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,949 ($564/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 6–19, 2026 (13 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($128/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 6–19, 2026 (13 nights)
- 1 bed/1 bath, sleeps 4
- $1,202 ($92/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,531 ($506/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 6–19, 2026 (13 nights)
- 2 bed/2 bath, sleeps 8
- $2,842 ($219/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 6–11, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $3,077 ($615/night)
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Voted Top Pick 2026
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Dec 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $944 ($189/night)
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Marriott's Phuket Beach Club
Phuket, Thailand- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Dec 6–11, 2026 (5 nights)
- 1 bed/2 bath, sleeps 6
- $1,439 ($288/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 6–11, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,990 ($598/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 6–11, 2026 (5 nights)
- 3 bed/2 bath, sleeps 10
- $932 ($186/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Dec 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $999 ($166/night)
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Tamarack Beach Resort
Carlsbad, California- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 6–10, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,330 ($332/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Dec 6–11, 2026 (5 nights)
- 1 bed/2 bath, sleeps 6
- $1,439 ($288/night)