Winter Rentals
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
- $10,380 ($1,483/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
- $5,638 ($806/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
- $6,565 ($938/night)
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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)
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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)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 8–15, 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
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,946 ($992/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,088 ($441/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,290 ($470/night)
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,894 ($556/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–13, 2026 (5 nights)
- Studio/1 bath, sleeps 2
- $1,932 ($386/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 1 bed/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 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,121 ($874/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–16, 2026 (8 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($303/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 8–14, 2026 (6 nights)
- 1 bed/2 bath, sleeps 4
- $2,804 ($467/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,641 ($377/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 9–16, 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 9–14, 2026 (5 nights)
- Studio/1 bath, sleeps 2
- $1,987 ($397/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 9–15, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $4,819 ($803/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 10–19, 2026 (9 nights)
- 3 bed/2 bath, sleeps 8
- $11,470 ($1,274/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Feb 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,123 ($303/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 10–15, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,368 ($474/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 11–17, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $1,824 ($304/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,858 ($408/night)
Verified & Protected
Kahana Beach Resort
Lahaina, Hawaii- Feb 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,925 ($275/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Feb 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($640/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/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)