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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
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The Banyan Resort
Key West, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($346/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $7,382 ($1,055/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $10,920 ($1,560/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–19, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $5,448 ($545/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Divi Dutch Village Beach Resort
Oranjestad, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,866 ($267/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,595 ($656/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,611 ($1,087/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,365 ($766/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,616 ($374/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
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Alexandra Resort and Spa
Grace Bay, Turks and Caicos Islands- Jan 9–16, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $6,701 ($957/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $18,191 ($2,599/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,252 ($750/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/night)
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Hacienda del Mar Resort
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,901 ($700/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,434 ($919/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 9–16, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,795 ($256/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,132 ($447/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($166/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,375 ($1,482/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Royal Islander Club la Plage
St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,440 ($206/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $11,470 ($1,639/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,783 ($398/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $10,488 ($1,498/night)
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Marriott's Villas at Doral
Miami, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $3,294 ($471/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,631 ($1,233/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,055 ($436/night)