Winter Rentals
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,303 ($329/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 4–11, 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- Jan 4–10, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $8,963 ($1,494/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,749 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,786 ($541/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 4–10, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($458/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,294 ($471/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 5–11, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($876/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $7,655 ($1,094/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,527 ($647/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,240 ($463/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($495/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,531 ($362/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 8–29, 2026 (21 nights)
- 2 bed/2 bath, sleeps 6
- $7,464 ($355/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Jan 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Jan 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,581 ($369/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,711 ($673/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,422 ($346/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,042 ($292/night)
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)
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
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)
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
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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/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 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
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
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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/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)
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/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
- $5,290 ($756/night)