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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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $20,625 ($2,946/night)
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Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,745 ($392/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 26–31, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $804 ($161/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,584 ($798/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,712 ($673/night)
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Garza Blanca Resort & Spa Cancun
Cancun, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $7,006 ($1,001/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 2 bed/2.5 bath, sleeps 6
- $19,645 ($3,274/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,546 ($1,078/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,924 ($1,561/night)
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Hyatt Hacienda Del Mar
Dorado, Puerto Rico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,813 ($545/night)
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Sunrise Lodge by Hilton Grand Vacations
Park City, Utah- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 26–31, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $4,630 ($926/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $4,385 ($626/night)
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Villa La Estancia Beach Resort & Spa Riviera Nayarit
Nuevo Vallarta, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,963 ($423/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,260 ($323/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($377/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,510 ($930/night)
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Hyatt High Sierra Lodge
Incline Village, Nevada- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($2,184/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,804 ($401/night)
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Hilton Club, The Central at 5th New York
New York City, New York- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $7,655 ($1,094/night)
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Club Wyndham Nashville
Nashville, Tennessee- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($87/night)
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Garza Blanca Resort & Spa Los Cabos
Cabo San Lucas, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $3,022 ($432/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,240 ($463/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,326 ($1,475/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,631 ($1,233/night)
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Marriott's Grand Chateau
Las Vegas, Nevada- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
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Hilton Club The Quin New York
New York City, New York- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $15,285 ($2,184/night)
The Galleon Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,458 ($494/night)
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Wyndham Reef Resort
East End, Grand Cayman, Cayman Islands- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,943 ($1,420/night)
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The Wren
Vail, Colorado- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($751/night)
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AAA 5-Diamond Award
Grand Luxxe at Vidanta Nuevo Vallarta
Nuevo Vallarta, Mexico- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $7,655 ($1,094/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Dec 26–31, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $924 ($185/night)