Winter Rentals
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,995 ($571/night)
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,783 ($969/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,250 ($464/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,835 ($548/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $10,920 ($1,560/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 2, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($513/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,004 ($572/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,202 ($315/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 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- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,995 ($1,856/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,995 ($714/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $14,995 ($2,142/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,995 ($2,142/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,500 ($1,071/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,470 ($781/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 1, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,385 ($277/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,276 ($325/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,763 ($1,109/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/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
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
Hanalei Bay Resort
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,791 ($256/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
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,306 ($329/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,995 ($1,142/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/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
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)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 28, 2025 – Jan 2, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $5,750 ($1,150/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
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
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
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
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 28, 2025 – Jan 2, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($572/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 29, 2025 – Jan 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,995 ($1,142/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
- $6,020 ($1,204/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)