Winter Rentals
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,204 ($315/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($284/night)
Verified & Protected
Maui Banyan Vacation Club
Kihei, Hawaii- Feb 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,660 ($237/night)
Verified & Protected
Maui Beach Vacation Club
Kihei, Hawaii- Feb 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 4–17, 2026 (13 nights)
- Studio/1 bath, sleeps 4
- $8,527 ($656/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,858 ($408/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Feb 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,238 ($891/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 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 North
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $10,925 ($1,561/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 6–9, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,327 ($442/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,303 ($329/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,121 ($874/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,204 ($315/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,598 ($657/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($665/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,764 ($538/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,294 ($471/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,368 ($338/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,821 ($689/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,366 ($767/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,380 ($1,483/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,470 ($1,639/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,199 ($1,171/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,543 ($363/night)
Verified & Protected
Paniolo Greens
Waikoloa Village, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($190/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)