Winter Rentals
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,887 ($984/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Feb 14–19, 2026 (5 nights)
- 1 bed/1 bath, sleeps 6
- $2,260 ($452/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,094 ($585/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,145 ($592/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/night)
Verified & Protected
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,925 ($1,561/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,818 ($260/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,617 ($1,374/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,600 ($1,086/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,500 ($1,071/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,617 ($1,374/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,925 ($704/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,714 ($245/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,688 ($384/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,274 ($1,039/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,818 ($260/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,004 ($572/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,963 ($423/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
The Gardens at West Maui
Kapalua, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,769 ($253/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,995 ($714/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 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 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,365 ($766/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,535 ($362/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $61,010 ($8,716/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)