Winter Rentals
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,654 ($236/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,740 ($1,249/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $3,508 ($501/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,432 ($1,062/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–26, 2025 (6 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($277/night)
Verified & Protected
Lifetime in Hawaii
Honolulu, Hawaii- Dec 20, 2025 – Jan 3, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($158/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,829 ($833/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,290 ($470/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 20–21, 2025 (1 night)
- Studio/1 bath, sleeps 4
- $791 ($791/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 20–26, 2025 (6 nights)
- Studio/1 bath, sleeps 4
- $3,862 ($644/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–26, 2025 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,211 ($702/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($315/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,859 ($408/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,957 ($708/night)
Verified & Protected
Kuhio Banyan Club
Honolulu, Hawaii- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $832 ($119/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,919 ($703/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–26, 2025 (5 nights)
- Studio/1 bath, sleeps 4
- $1,385 ($277/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,086 ($1,155/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 21–27, 2025 (6 nights)
- 1 bed/2 bath, sleeps 4
- $3,944 ($657/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,271 ($610/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 21–27, 2025 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($495/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–26, 2025 (5 nights)
- Studio/1 bath, sleeps 4
- $1,217 ($243/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
WorldMark Kihei Resort
Kihei, Hawaii- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $3,069 ($438/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,175 ($739/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,102 ($872/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 3
- $1,976 ($282/night)