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 Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,179 ($436/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,524 ($1,646/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,326 ($1,475/night)
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Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Eagle's Nest Beach Resort
Marco Island, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,802 ($543/night)
Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,978 ($283/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,944 ($1,421/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–21, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $764 ($255/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Club Wyndham Smoky Mountains
Sevierville, Tennessee- Dec 18–31, 2026 (13 nights)
- 2 bed/2 bath, sleeps 8
- $2,746 ($211/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,474 ($496/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,072 ($439/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,740 ($1,249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,222 ($603/night)
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The Manhattan Club
New York City, New York- Dec 18–20, 2026 (2 nights)
- 1 bed/2 bath, sleeps 4
- $1,440 ($720/night)
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La Cabana Beach Resort
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,542 ($506/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,786 ($827/night)
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Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Elara by Hilton Grand Vacations
Las Vegas, Nevada- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $13,104 ($1,872/night)
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The Summit at Massanutten
McGaheysville, Virginia- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $1,219 ($174/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,908 ($1,273/night)
Costa Linda Beach Resort
Oranjestad, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,584 ($798/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
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The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,069 ($438/night)
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Hilton Vacation Club Lake Tahoe Resort
South Lake Tahoe, California- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,407 ($1,201/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $21,770 ($1,555/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 19–26, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $18,555 ($2,651/night)
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Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 3 bed/4 bath, sleeps 10
- $10,925 ($1,561/night)
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Corazon Cabo Resort & Spa
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,306 ($472/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,150 ($307/night)
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Zoetry Casa del Mar Los Cabos
San Jose del Cabo, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,946 ($707/night)
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Villa del Palmar Cabo San Lucas
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $2,423 ($346/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,867 ($1,552/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $5,358 ($765/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $9,830 ($1,404/night)
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Grand Residences by Royal Resorts
Puerto Morelos, Mexico- Dec 19–26, 2026 (7 nights)
- 1 bed/1.5 bath, sleeps 5
- $3,840 ($549/night)