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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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,526 ($1,218/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,476 ($211/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,749 ($393/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $9,018 ($1,503/night)
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Grand Luxxe Spa Suites at Vidanta Nuevo Vallarta
Nuevo Vallarta, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,834 ($1,405/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,810 ($401/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,132 ($447/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,285 ($1,326/night)
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Holiday Inn Club Vacations at Smoky Mountain Resort
Gatlinburg, Tennessee- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $18,882 ($2,697/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $10,489 ($2,622/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,378 ($1,911/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,425 ($1,346/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($2,184/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,876 ($696/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($1,560/night)
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Voted Top Pick 2026
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,948 ($564/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,417 ($1,202/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,260 ($323/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,560 ($1,794/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,121 ($874/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $10,380 ($1,483/night)
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Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $5,366 ($767/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,180 ($1,311/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,810 ($401/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,758 ($1,965/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $5,440 ($777/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,276 ($325/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($922/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,326 ($221/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,772 ($396/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,526 ($1,218/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,748 ($821/night)