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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,053 ($865/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,109 ($1,016/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 3–17, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,667 ($191/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,598 ($657/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,255 ($209/night)
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Westgate Park City Resort & Spa
Park City, Utah- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,456 ($637/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,620 ($231/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–7, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $995 ($249/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,052 ($175/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,488 ($298/night)
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Westgate Las Vegas Resort & Casino
Las Vegas, Nevada- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,242 ($248/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,884 ($983/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,527 ($505/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,906 ($844/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,611 ($516/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($636/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,165 ($166/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,508 ($501/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,734 ($248/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $9,398 ($1,343/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–16, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,000 ($154/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,872 ($1,125/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Club Wyndham Harbour Lights
San Diego, California- Jan 3–7, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $639 ($160/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 3–7, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,277 ($319/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,982 ($1,140/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 3–10, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $8,200 ($1,171/night)
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Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($107/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 3–6, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $483 ($161/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,594 ($319/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($440/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($1,313/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $4,053 ($811/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,396 ($465/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 3–11, 2027 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($461/night)
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Grand Timber Lodge
Breckenridge, Colorado- Jan 3–10, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $5,230 ($747/night)