Winter Rentals
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
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
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,104 ($443/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,018 ($1,288/night)
Verified & Protected
Maui Schooner
Kihei, Hawaii- Feb 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,358 ($194/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,380 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,094 ($585/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,145 ($592/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,925 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 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- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,829 ($547/night)
Verified & Protected
The Gardens at West Maui
Kapalua, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,769 ($253/night)
Verified & Protected
Voted Top Pick 2025
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)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $13,378 ($1,911/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,993 ($1,713/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2025
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)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,330 ($619/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($284/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,150 ($307/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,560 ($937/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,925 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)