Winter Rentals
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,548 ($650/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($284/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $944 ($135/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 14–19, 2025 (5 nights)
- Studio/1 bath, sleeps 2
- $1,385 ($277/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 15–21, 2025 (6 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($912/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 16–21, 2025 (5 nights)
- Studio/1 bath, sleeps 2
- $999 ($200/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 16–20, 2025 (4 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($166/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 17–21, 2025 (4 nights)
- Studio/1 bath, sleeps 4
- $888 ($222/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 17–20, 2025 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,099 ($366/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 17–21, 2025 (4 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($278/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,768 ($253/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 18, 2025 – Jan 1, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($329/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,478 ($354/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,489 ($641/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 19–26, 2025 (7 nights)
- 4 bed/4 bath, sleeps 10
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,450 ($636/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–27, 2025 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($276/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 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
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/night)
Verified & Protected
Kauai Beach Villas
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/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
Hanalei Bay Resort
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/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
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $944 ($135/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,493 ($642/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
The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Pono Kai
Kapaa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/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
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,835 ($548/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
The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)