Winter Rentals
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 21–23, 2025 (2 nights)
- 2 bed/2 bath, sleeps 8
- $888 ($444/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
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $16,375 ($2,339/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 Waiohai Beach Club
Koloa, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,374 ($625/night)
Verified & Protected
Kauai Beach Villas
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,096 ($299/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
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/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 Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($315/night)
Verified & Protected
Kuhio Banyan Club
Honolulu, Hawaii- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $832 ($119/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
- $4,385 ($626/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
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–26, 2025 (5 nights)
- Studio/1 bath, sleeps 4
- $1,219 ($244/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 21, 2025 – Jan 2, 2026 (12 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($438/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
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/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
- $8,200 ($1,171/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,200 ($314/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
Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1.5 bath, sleeps 4
- $610 ($87/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
- $4,930 ($704/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)
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
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 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 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/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 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 Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,919 ($703/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
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/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
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
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
Maui Beach Vacation Club
Kihei, Hawaii- Dec 21, 2025 – Jan 4, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($235/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's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,053 ($579/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–28, 2025 (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- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,102 ($872/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
Club Wyndham Shearwater
Princeville, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 22–27, 2025 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,096 ($419/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 22–25, 2025 (3 nights)
- 1 bed/2 bath, sleeps 4
- $1,165 ($388/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 22–26, 2025 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,986 ($496/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 22–28, 2025 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,495 ($749/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 22–27, 2025 (5 nights)
- Studio/1 bath, sleeps 2
- $1,330 ($266/night)