Winter Rentals
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
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
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
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/2 bath, sleeps 4
- $5,470 ($781/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,306 ($329/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,250 ($464/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,292 ($327/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($377/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 29, 2025 – Jan 3, 2026 (5 nights)
- 3 bed/3 bath, sleeps 8
- $5,797 ($1,159/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
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 30, 2025 – Jan 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,688 ($384/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 30, 2025 – Jan 5, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,181 ($530/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 31, 2025 – Jan 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($942/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
- $5,038 ($720/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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
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
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,204 ($315/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
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,291 ($327/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 4–7, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($480/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 Cliffs at Princeville
Princeville, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,390 ($341/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/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
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($495/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)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Jan 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,581 ($369/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,948 ($564/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Jan 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,851 ($264/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,390 ($341/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,001 ($429/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
WorldMark Kapaa Shore
Kapaa, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($284/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 18–24, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,379 ($397/night)