Winter Rentals
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
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 21–27, 2025 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($495/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
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
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
Kauai Beach Villas
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,096 ($299/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 21–26, 2025 (5 nights)
- Studio/1 bath, sleeps 4
- $1,385 ($277/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
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 21–26, 2025 (5 nights)
- Studio/1 bath, sleeps 4
- $1,217 ($243/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 Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,175 ($739/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 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
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
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
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's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,660 ($237/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)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 22–28, 2025 (6 nights)
- Studio/1 bath, sleeps 4
- $3,949 ($658/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
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 22–27, 2025 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,096 ($419/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 23–30, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,404 ($486/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 23–28, 2025 (5 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($441/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 23–28, 2025 (5 nights)
- 1 bed/1 bath, sleeps 4
- $10,925 ($2,185/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 24–26, 2025 (2 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($1,102/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 24–28, 2025 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($332/night)
Verified & Protected
Club Wyndham at Waikiki Beach Walk
Honolulu, Hawaii- Dec 24–27, 2025 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,275 ($425/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 24, 2025 – Jan 1, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $6,892 ($862/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 26–29, 2025 (3 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($808/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,659 ($237/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 4 bed/4 bath, sleeps 10
- $4,603 ($658/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $20,626 ($2,947/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $999 ($143/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 26–29, 2025 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($443/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,949 ($421/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $8,995 ($1,285/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,932 ($276/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,303 ($329/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,368 ($338/night)
Verified & Protected
Kahana Villa Resort
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)