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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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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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
- $10,925 ($1,561/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,181 ($454/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9 – Feb 6, 2027 (28 nights)
- 3 bed/2.5 bath, sleeps 8
- $26,883 ($960/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,898 ($1,557/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/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 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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,497 ($500/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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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/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 8
- $4,140 ($591/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,821 ($689/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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/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
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 2
- $1,330 ($266/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–14, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,074 ($519/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
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,596 ($766/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,438 ($406/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 8
- $4,412 ($630/night)
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Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,749 ($393/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
- $7,110 ($1,016/night)
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/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 Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 11–18, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,914 ($416/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 12–21, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $4,080 ($453/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 12–21, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $3,539 ($393/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 12–19, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,658 ($237/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,726 ($532/night)
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WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 14–24, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($275/night)
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Lawai Beach Resort
Koloa, Hawaii- Jan 14–28, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,434 ($460/night)
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The Cliffs at Princeville
Princeville, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,611 ($802/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,611 ($802/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,368 ($338/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)