Winter Rentals
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,692 ($813/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,925 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,786 ($541/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,456 ($922/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,839 ($548/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,214 ($1,031/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
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 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,944 ($563/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($580/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Kahana Beach Resort
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,131 ($304/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 22 – Mar 1, 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 22 – Mar 1, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,622 ($517/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,611 ($516/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
Verified & Protected
Voted Top Pick 2025
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 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 22 – Mar 1, 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 23 – Mar 2, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $5,800 ($829/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 23–28, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($921/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 23–28, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($615/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 24 – Mar 4, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($521/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 25 – Mar 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 25 – Mar 2, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,967 ($593/night)
Verified & Protected
Imperial Hawaii Vacation Club
Honolulu, Hawaii- Feb 25 – Mar 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,742 ($249/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 25 – Mar 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($268/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Feb 26 – Mar 5, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,260 ($323/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 26 – Mar 5, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 26 – Mar 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,276 ($611/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
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)