Winter Rentals
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,568 ($510/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,858 ($408/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,207 ($315/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1.5 bath, sleeps 4
- $1,385 ($198/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,150 ($307/night)
Verified & Protected
Hono Koa Resort
Honokowai, Hawaii- Feb 28 – Mar 14, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $5,351 ($382/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,039 ($434/night)
Verified & Protected
Kahana Falls
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 6, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($440/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $14,086 ($2,012/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/1 bath, sleeps 6
- $2,559 ($366/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,551 ($793/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,437 ($1,062/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 14, 2026 (14 nights)
- Studio/1 bath, sleeps 4
- $5,475 ($391/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,632 ($1,090/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,663 ($380/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,783 ($969/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $13,378 ($1,911/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/1 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)