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 Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,723 ($1,246/night)
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Royal Islander Club la Plage
St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,440 ($206/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 2–7, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,284 ($657/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,584 ($798/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,802 ($829/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $12,996 ($1,857/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,924 ($561/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Hyatt Main Street Station, A Hyatt Residence Club
Breckenridge, Colorado- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $4,712 ($673/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $7,382 ($1,055/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,821 ($403/night)
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The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 2–8, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,640 ($440/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,206 ($744/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($174/night)
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Grand Solmar Pacific Dunes Resort Golf & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,358 ($765/night)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,797 ($828/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,960 ($280/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,095 ($299/night)
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Paniolo Greens
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $547 ($182/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–16, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $8,647 ($618/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $875 ($292/night)
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Club Wyndham Austin
Austin, Texas- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,559 ($520/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $15,285 ($2,184/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,271 ($610/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $13,105 ($1,872/night)
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Villa La Estancia Cabo San Lucas
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/4 bath, sleeps 8
- $8,745 ($1,249/night)
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,707 ($672/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,053 ($579/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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The Galleon Resort
Key West, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,464 ($1,066/night)