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 MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Club Wyndham Long Wharf
Newport, Rhode Island- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $839 ($120/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,260 ($323/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
- $2,398 ($343/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,109 ($1,016/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
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,731 ($533/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
- $7,110 ($1,016/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 8
- $5,202 ($743/night)
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
- $6,783 ($969/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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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
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–12, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
The Mill Resort & Suites
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/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
- $17,465 ($2,495/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–12, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $331 ($110/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
- $4,766 ($681/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
- $4,031 ($576/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,631 ($1,233/night)
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Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/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
- $2,641 ($377/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/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
- $7,219 ($1,031/night)
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Alexandra Resort and Spa
Grace Bay, Turks and Caicos Islands- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,385 ($626/night)
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Marriott's Summit Watch
Park City, Utah- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,276 ($611/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 Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,807 ($544/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)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Playa Grande Resort & Grand Spa
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,879 ($268/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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Sunrise Lodge by Hilton Grand Vacations
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/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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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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WorldMark Kihei Resort
Kihei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,096 ($299/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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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/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
- $7,083 ($1,012/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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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
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Club Wyndham Inn on Long Wharf
Newport, Rhode Island- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $503 ($72/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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Marriott's Desert Springs Villas
Palm Desert, California- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/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
- $4,817 ($688/night)