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
- $6,020 ($860/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
- $2,532 ($362/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,604 ($434/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $887 ($177/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($331/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,213 ($243/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–15, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($594/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–15, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $7,107 ($1,421/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 10–17, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $14,740 ($2,106/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,038 ($720/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,598 ($1,514/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,671 ($810/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 10–13, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,346 ($449/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,726 ($1,389/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,892 ($1,149/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($714/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–14, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,772 ($693/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($397/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,881 ($983/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 10–15, 2027 (5 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,925 ($2,185/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,712 ($542/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $3,082 ($616/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($397/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–14, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($497/night)
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Hyatt Beach House Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,914 ($416/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,510 ($1,085/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($1,035/night)
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Marriott's Summit Watch
Park City, Utah- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,314 ($463/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,802 ($467/night)