Winter Rentals
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 28, 2025 – Jan 3, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $7,750 ($1,292/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,791 ($256/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
Maui Beach Vacation Club
Kihei, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,995 ($714/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,500 ($1,929/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 28, 2025 – Jan 1, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $4,750 ($1,188/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,995 ($1,571/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,250 ($464/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,147 ($735/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 29, 2025 – Jan 3, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($1,073/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 29, 2025 – Jan 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,995 ($1,142/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 29, 2025 – Jan 2, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,499 ($625/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 29, 2025 – Jan 3, 2026 (5 nights)
- 3 bed/3 bath, sleeps 8
- $5,692 ($1,138/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 29, 2025 – Jan 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 29, 2025 – Jan 4, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $6,895 ($1,149/night)
Verified & Protected
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 29, 2025 – Jan 5, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,200 ($314/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 30, 2025 – Jan 5, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $6,999 ($1,166/night)
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 30, 2025 – Jan 3, 2026 (4 nights)
- 3 bed/3 bath, sleeps 8
- $2,968 ($742/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 30, 2025 – Jan 4, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($266/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 30, 2025 – Jan 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 30, 2025 – Jan 5, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,181 ($530/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 30, 2025 – Jan 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,688 ($384/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 30, 2025 – Jan 2, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($1,098/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 31, 2025 – Jan 1, 2026 (1 night)
- 1 bed/1 bath, sleeps 4
- $1,275 ($1,275/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Dec 31, 2025 – Jan 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 31, 2025 – Jan 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($942/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 31, 2025 – Jan 4, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $5,250 ($1,313/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 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- Jan 2–9, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $6,342 ($906/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,998 ($857/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($930/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,970 ($424/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,276 ($611/night)