Winter Rentals
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,707 ($672/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $7,655 ($1,094/night)
Verified & Protected
Kahana Beach Resort
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($284/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,949 ($564/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,015 ($1,716/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,204 ($315/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $61,010 ($8,716/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,565 ($938/night)
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Maui Banyan Vacation Club
Kihei, Hawaii- Feb 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,085 ($298/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,422 ($346/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,053 ($579/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 17–27, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($766/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,420 ($774/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,966 ($852/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,058 ($580/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,290 ($1,327/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,028 ($1,004/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–24, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($917/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($253/night)
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Kahana Beach Resort
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
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Maui Banyan Vacation Club
Kihei, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,085 ($298/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 22–28, 2026 (6 nights)
- 3 bed/2 bath, sleeps 8
- $6,565 ($1,094/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 23 – Mar 2, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,511 ($502/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 24–28, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,636 ($659/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 25 – Mar 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,467 ($352/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 25 – Mar 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($190/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Kahana Falls
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,385 ($198/night)