Winter Rentals
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/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
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
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
The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/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
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,925 ($275/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/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
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,058 ($437/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
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,385 ($198/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
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 20–26, 2025 (6 nights)
- Studio/1 bath, sleeps 4
- $4,080 ($680/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/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
Kahana Falls
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,110 ($159/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–26, 2025 (6 nights)
- 1 bed/2 bath, sleeps 4
- $1,824 ($304/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
- $2,260 ($323/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
- $5,366 ($767/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,560 ($937/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
- $3,295 ($471/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
- $8,522 ($1,217/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/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
- $3,840 ($549/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($268/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,358 ($194/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,631 ($1,233/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
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/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
- $5,257 ($751/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,489 ($641/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,805 ($686/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/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
- $3,512 ($502/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,094 ($728/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
- $2,478 ($354/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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/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
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/night)