Winter Rentals
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,731 ($533/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,292 ($899/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,655 ($1,094/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($659/night)
Verified & Protected
Kalia Suites by Hilton Grand Vacations
Honolulu, Hawaii- Jan 10–18, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($412/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,851 ($264/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,740 ($1,249/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Jan 10–17, 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- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 10–17, 2026 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $6,347 ($907/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($580/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,948 ($564/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,711 ($673/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,696 ($528/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,194 ($599/night)
Verified & Protected
Maui Beach Vacation Club
Kihei, Hawaii- Jan 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,390 ($341/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,673 ($953/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,339 ($620/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,001 ($429/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($386/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Jan 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,384 ($626/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 16–23, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,069 ($438/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 16–19, 2026 (3 nights)
- 1 bed/1 bath, sleeps 5
- $2,968 ($989/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,963 ($1,280/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
WorldMark Kapaa Shore
Kapaa, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Verified & Protected
Maui Lea at Maui Hill
Kihei, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,153 ($450/night)