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 #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,218 ($1,031/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–13, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,861 ($310/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–13, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,795 ($299/night)
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Villa La Estancia Cabo San Lucas
Cabo San Lucas, Mexico- Jan 7–10, 2027 (3 nights)
- 2 bed/3 bath, sleeps 6
- $2,096 ($699/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–16, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $2,680 ($298/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–16, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,475 ($164/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–16, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $2,680 ($298/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 7–12, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 7–13, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($164/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 8–13, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $852 ($170/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $12,996 ($1,857/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,237 ($891/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 8–13, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,276 ($255/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,200 ($1,171/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 8–13, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($310/night)
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Marriott's Summit Watch
Park City, Utah- Jan 8–12, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,640 ($660/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,654 ($1,093/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 8–15, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $14,140 ($2,020/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 8–13, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($310/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,987 ($855/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 8–11, 2027 (3 nights)
- 3 bed/3 bath, sleeps 10
- $3,622 ($1,207/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 8–13, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 8–15, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,001 ($429/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 8–12, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,760 ($440/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 8–15, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $3,294 ($471/night)
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Kona Coast Resort
Kailua-Kona, Hawaii- Jan 8–22, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $4,058 ($290/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,294 ($471/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 8–12, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,188 ($547/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Royal Haciendas
Playa del Carmen, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,712 ($673/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $935 ($312/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
- $7,464 ($1,066/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
- $6,085 ($869/night)
Royal Haciendas
Playa del Carmen, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/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
- $3,186 ($455/night)