Winter Rentals
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
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
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/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)
- Studio/1 bath, sleeps 4
- $3,076 ($439/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
- $2,505 ($358/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)
- Studio/1 bath, sleeps 4
- $3,076 ($439/night)
Verified & Protected
Pono Kai
Kapaa, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,660 ($237/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/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
- $4,494 ($642/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
- $3,077 ($440/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
- $4,385 ($626/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,294 ($471/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)
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
- $2,750 ($393/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,560 ($937/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/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
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
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
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
- $6,020 ($860/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
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
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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/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 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
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
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
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/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
- $6,456 ($922/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
- $4,739 ($677/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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $12,337 ($1,762/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
The Point at Poipu
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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)
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
Lahaina, Hawaii- Feb 28 – Mar 7, 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 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,404 ($486/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,712 ($673/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
- $3,294 ($471/night)