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
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
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, 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
Lawai Beach Resort
Koloa, Hawaii- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,768 ($253/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
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
- $4,450 ($636/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
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
- $4,412 ($630/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
- $4,930 ($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
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–26, 2025 (6 nights)
- 2 bed/2 bath, sleeps 8
- $6,778 ($1,130/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)
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
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)
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
Lawai Beach Resort
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,385 ($198/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
- $7,650 ($1,093/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
- $4,930 ($704/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
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
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
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
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
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
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
- $1,659 ($237/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
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
- $7,763 ($1,109/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
- $9,181 ($1,312/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 29, 2025 – Jan 3, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($1,204/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 30, 2025 – Jan 2, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($1,098/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 3–17, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($294/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,294 ($471/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 8–29, 2026 (21 nights)
- 2 bed/2 bath, sleeps 6
- $7,464 ($355/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,042 ($292/night)