Winter Rentals
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 21 – Feb 4, 2026 (14 nights)
- 1 bed/2 bath, sleeps 4
- $6,129 ($438/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,162 ($1,452/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,342 ($906/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,285 ($1,326/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,963 ($1,280/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,191 ($456/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 26 – Feb 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,832 ($690/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 28 – Feb 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,422 ($346/night)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 28 – Feb 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 30 – Feb 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,204 ($315/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 30 – Feb 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 30 – Feb 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,892 ($699/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,177 ($1,311/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,631 ($519/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,145 ($592/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,903 ($1,558/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,952 ($1,279/night)
Verified & Protected
One Napili Way
Lahaina, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 3 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 1–8, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 1–6, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $3,159 ($632/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 1–8, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,655 ($522/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 1–8, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,072 ($439/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 1–8, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,039 ($434/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 1–8, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $4,167 ($595/night)