Winter Rentals
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
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
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
The Point at Poipu
Koloa, Hawaii- Jan 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,749 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,554 ($936/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 25 – Feb 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 27 – Feb 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 27 – Feb 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,858 ($408/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 29 – Feb 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 31 – Feb 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,256 ($751/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,967 ($424/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,858 ($408/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Feb 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,428 ($347/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 6–9, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,327 ($442/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,858 ($408/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Feb 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,034 ($719/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,342 ($906/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,887 ($984/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,839 ($548/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 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- Feb 14–21, 2026 (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- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,946 ($992/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 15–22, 2026 (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- Feb 15–22, 2026 (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- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 17–27, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($793/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 21 – Mar 7, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($547/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/night)