Winter Rentals
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/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 Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,745 ($392/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)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
Verified & Protected
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/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 8
- $7,105 ($1,015/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,382 ($483/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,145 ($306/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($930/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,786 ($631/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,858 ($408/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
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 8
- $4,369 ($624/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 8
- $4,712 ($673/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
The Point at Poipu
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/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
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
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
- $4,603 ($658/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
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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/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 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
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
- $5,475 ($782/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 Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)