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 Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,707 ($1,530/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,053 ($579/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,772 ($396/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,554 ($936/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,320 ($903/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,711 ($673/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($922/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,240 ($463/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,676 ($525/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,595 ($656/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 13–18, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,050 ($610/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,858 ($408/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,074 ($868/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($354/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,565 ($938/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,712 ($673/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,468 ($495/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,556 ($937/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 16–21, 2026 (5 nights)
- 2 bed/3 bath, sleeps 8
- $4,112 ($822/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,361 ($766/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,162 ($595/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,309 ($1,187/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,493 ($642/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,053 ($722/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,740 ($1,249/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,560 ($937/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,801 ($829/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,763 ($1,109/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,582 ($1,226/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–26, 2026 (8 nights)
- 1 bed/2 bath, sleeps 4
- $6,996 ($874/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,274 ($1,039/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $13,050 ($1,864/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,039 ($720/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,835 ($1,405/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,272 ($1,039/night)