https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii/Kauai en Tue, 26 May 2026 02:56:07 -0700 3600 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,671 ($810/night)

]]> https://www.redweek.com/posting/R1434890 Thu, 19 Feb 2026 12:27:28 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 3–12, 2026 (9 nights)
• 2 bed/2 bath, sleeps 8
• $8,200 ($911/night)

]]> https://www.redweek.com/posting/R1443767 Tue, 17 Mar 2026 08:00:24 -0700 Verified & Protected

Makai Club Resort

Princeville, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,749 ($393/night)

]]> https://www.redweek.com/posting/R1438655 Tue, 17 Mar 2026 18:56:32 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1471957 Wed, 13 May 2026 08:23:14 -0700 Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,347 ($907/night)

]]> https://www.redweek.com/posting/R1467204 Thu, 30 Apr 2026 09:20:50 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,475 ($782/night)

]]> https://www.redweek.com/posting/R1470898 Mon, 11 May 2026 14:19:05 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,099 ($728/night)

]]> https://www.redweek.com/posting/R1450066 Tue, 31 Mar 2026 07:21:57 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1403799 Fri, 19 Dec 2025 11:48:39 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1446449 Mon, 23 Mar 2026 06:15:38 -0700 Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Dec 6–13, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,807 ($544/night)

]]> https://www.redweek.com/posting/R1464310 Fri, 24 Apr 2026 09:51:22 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,361 ($766/night)

]]> https://www.redweek.com/posting/R1471440 Tue, 12 May 2026 10:44:02 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,475 ($782/night)

]]> https://www.redweek.com/posting/R1421982 Tue, 27 Jan 2026 05:55:41 -0800 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,549 ($221/night)

]]> https://www.redweek.com/posting/R1471362 Mon, 11 May 2026 11:00:26 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,772 ($253/night)

]]> https://www.redweek.com/posting/R1464356 Fri, 24 Apr 2026 18:01:16 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1459472 Tue, 14 Apr 2026 09:45:45 -0700 Verified & Protected

The Point at Poipu

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1368333 Mon, 01 Dec 2025 14:15:20 -0800 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 12–16, 2026 (4 nights)
• 1 bed/2 bath, sleeps 4
• $1,769 ($442/night)

]]> https://www.redweek.com/posting/R1451535 Mon, 30 Mar 2026 10:03:03 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1471539 Tue, 12 May 2026 12:33:54 -0700 Verified & Protected

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,712 ($673/night)

]]> https://www.redweek.com/posting/R1473992 Tue, 19 May 2026 04:18:36 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,876 ($696/night)

]]> https://www.redweek.com/posting/R1440995 Tue, 03 Mar 2026 09:55:10 -0800 Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

• Dec 12–19, 2026 (7 nights)
• 1 bed/2 bath, sleeps 6
• $4,031 ($576/night)

]]> https://www.redweek.com/posting/R1408351 Thu, 15 Jan 2026 15:52:49 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1456495 Mon, 06 Apr 2026 14:47:57 -0700 Verified & Protected

The Point at Poipu

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1413641 Tue, 13 Jan 2026 08:28:25 -0800 Verified & Protected

Sheraton Kauai Resort Villas

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $7,110 ($1,016/night)

]]> https://www.redweek.com/posting/R1466037 Tue, 05 May 2026 12:40:52 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,494 ($642/night)

]]> https://www.redweek.com/posting/R1454836 Wed, 01 Apr 2026 07:41:34 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1443409 Mon, 20 Apr 2026 09:55:21 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1450165 Wed, 25 Mar 2026 13:35:45 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,494 ($642/night)

]]> https://www.redweek.com/posting/R1453988 Wed, 01 Apr 2026 09:36:31 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 13–20, 2026 (7 nights)
• Studio/1 bath, sleeps 3
• $2,968 ($424/night)

]]> https://www.redweek.com/posting/R1438927 Mon, 09 Mar 2026 13:38:35 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 14–20, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $4,440 ($740/night)

]]> https://www.redweek.com/posting/R1397913 Mon, 22 Dec 2025 08:55:04 -0800 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 16–23, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,497 ($500/night)

]]> https://www.redweek.com/posting/R1459708 Tue, 14 Apr 2026 14:13:54 -0700 Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

• Dec 18–25, 2026 (7 nights)
• 4 bed/4 bath, sleeps 12
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1473625 Fri, 22 May 2026 12:20:50 -0700 Verified & Protected

Lawai Beach Resort

Koloa, Hawaii

• Dec 18, 2026 – Jan 1, 2027 (14 nights)
• 1 bed/1 bath, sleeps 4
• $7,328 ($523/night)

]]> https://www.redweek.com/posting/R1425763 Thu, 26 Mar 2026 14:11:18 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 18–25, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,949 ($564/night)

]]> https://www.redweek.com/posting/R1462601 Tue, 21 Apr 2026 08:55:21 -0700 Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

• Dec 18, 2026 – Jan 1, 2027 (14 nights)
• 1 bed/2 bath, sleeps 8
• $7,655 ($547/night)

]]> https://www.redweek.com/posting/R1466693 Mon, 04 May 2026 10:22:52 -0700 Verified & Protected

Hanalei Bay Resort

Princeville, Hawaii

• Dec 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,211 ($602/night)

]]> https://www.redweek.com/posting/R1322235 Thu, 14 Aug 2025 17:33:19 -0700 Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Dec 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,274 ($1,039/night)

]]> https://www.redweek.com/posting/R1442977 Sat, 14 Mar 2026 04:13:53 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 18–25, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1472785 Fri, 15 May 2026 08:03:08 -0700 Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,647 ($1,092/night)

]]> https://www.redweek.com/posting/R1456939 Tue, 07 Apr 2026 06:06:01 -0700 Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,118 ($874/night)

]]> https://www.redweek.com/posting/R1457435 Tue, 07 Apr 2026 06:13:03 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1406635 Tue, 30 Dec 2025 12:49:01 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,285 ($755/night)

]]> https://www.redweek.com/posting/R1406092 Wed, 24 Dec 2025 08:43:17 -0800 Verified & Protected

The Point at Poipu

Koloa, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,930 ($704/night)

]]> https://www.redweek.com/posting/R1406020 Fri, 26 Dec 2025 09:13:20 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,802 ($829/night)

]]> https://www.redweek.com/posting/R1365455 Wed, 12 Nov 2025 07:40:59 -0800 Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Dec 19–26, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,568 ($510/night)

]]> https://www.redweek.com/posting/R1463724 Thu, 23 Apr 2026 11:30:40 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1406631 Tue, 30 Dec 2025 12:49:43 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1351684 Mon, 20 Oct 2025 09:57:39 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,402 ($914/night)

]]> https://www.redweek.com/posting/R1447974 Tue, 17 Mar 2026 17:48:55 -0700