Winter Rentals
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/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)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/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 Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/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
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
- $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
- $4,930 ($704/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
Hanalei Bay Resort
Princeville, Hawaii- Dec 21–28, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,200 ($314/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
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
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
- $5,038 ($720/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
Club Wyndham Shearwater
Princeville, Hawaii- Dec 21–28, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/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
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
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 Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2025 (7 nights)
- Studio/1 bath, sleeps 3
- $1,976 ($282/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
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
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 22–27, 2025 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,042 ($408/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
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
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 23–26, 2025 (3 nights)
- 2 bed/2 bath, sleeps 6
- $999 ($333/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
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)
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
- $2,042 ($292/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,544 ($221/night)
Verified & Protected
Makai Club Resort
Princeville, Hawaii- Dec 26, 2025 – Jan 9, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($313/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
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,201 ($314/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
Hanalei Bay Resort
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/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)
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
- $8,418 ($1,203/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
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
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
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
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,000 ($1,000/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 1, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($332/night)