Winter Rentals
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 19–26, 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- Jan 21 – Feb 4, 2026 (14 nights)
- 1 bed/2 bath, sleeps 4
- $6,129 ($438/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,749 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $5,910 ($844/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,782 ($969/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 23–30, 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- Jan 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,726 ($532/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,554 ($936/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,887 ($984/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($377/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,191 ($456/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,778 ($968/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,162 ($1,452/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,285 ($1,326/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,342 ($906/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,963 ($1,280/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 25 – Feb 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,527 ($361/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 25 – Feb 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- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,214 ($1,031/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 26 – Feb 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,832 ($690/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 27 – Feb 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 27 – Feb 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,858 ($408/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 28 – Feb 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,802 ($829/night)
Verified & Protected
Maui Beach Vacation Club
Kihei, Hawaii- Jan 28 – Feb 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 28 – Feb 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,422 ($346/night)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 28 – Feb 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 29 – Feb 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($354/night)
Verified & Protected
Kona Reef
Kailua-Kona, Hawaii- Jan 29 – Feb 5, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)