https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii en Fri, 18 Sep 2026 04:12:17 -0700 3600 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $6,816 ($974/night)

]]> https://www.redweek.com/posting/R1411325 Wed, 07 Jan 2026 07:53:14 -0800 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 1–6, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $3,121 ($624/night)

]]> https://www.redweek.com/posting/R1525000 Thu, 17 Sep 2026 10:50:52 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 1–6, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,423 ($485/night)

]]> https://www.redweek.com/posting/R1471899 Tue, 19 May 2026 09:00:22 -0700 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
• $3,832 ($547/night)

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

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,595 ($656/night)

]]> https://www.redweek.com/posting/R1503381 Mon, 27 Jul 2026 13:57:15 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

• Dec 1–6, 2026 (5 nights)
• 1 bed/2 bath, sleeps 4
• $2,478 ($496/night)

]]> https://www.redweek.com/posting/R1511868 Wed, 19 Aug 2026 14:27:38 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• 3 bed/3 bath, sleeps 10
• $7,862 ($1,310/night)

]]> https://www.redweek.com/posting/R1412939 Tue, 06 Jan 2026 08:35:14 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $5,911 ($844/night)

]]> https://www.redweek.com/posting/R1396693 Thu, 04 Dec 2025 19:07:57 -0800 Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 1–8, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $1,742 ($249/night)

]]> https://www.redweek.com/posting/R1508554 Fri, 07 Aug 2026 12:31:07 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

• Dec 1–6, 2026 (5 nights)
• 1 bed/2 bath, sleeps 4
• $2,478 ($496/night)

]]> https://www.redweek.com/posting/R1511870 Fri, 14 Aug 2026 08:28:54 -0700 Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/2 bath, sleeps 6
• $1,512 ($216/night)

]]> https://www.redweek.com/posting/R1439465 Thu, 07 May 2026 07:33:18 -0700 Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,230 ($319/night)

]]> https://www.redweek.com/posting/R1407461 Fri, 26 Dec 2025 12:44:20 -0800 Verified & Protected

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

• Dec 2–7, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,654 ($331/night)

]]> https://www.redweek.com/posting/R1448659 Wed, 06 May 2026 15:07:58 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,568 ($510/night)

]]> https://www.redweek.com/posting/R1478058 Tue, 02 Jun 2026 06:55:13 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,707 ($672/night)

]]> https://www.redweek.com/posting/R1486313 Fri, 19 Jun 2026 09:53:44 -0700 Verified & Protected

Kahana Falls

Lahaina, Hawaii

• Dec 3–10, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $2,096 ($299/night)

]]> https://www.redweek.com/posting/R1440983 Wed, 01 Apr 2026 14:58:25 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 3–7, 2026 (4 nights)
• Studio/1 bath, sleeps 4
• $2,188 ($547/night)

]]> https://www.redweek.com/posting/R1483217 Fri, 12 Jun 2026 17:08:39 -0700 Verified & Protected

WorldMark Kona Resort

Kailua-Kona, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1518228 Mon, 31 Aug 2026 13:12:06 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,268 ($467/night)

]]> https://www.redweek.com/posting/R1459563 Mon, 13 Apr 2026 11:17:52 -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 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,619 ($374/night)

]]> https://www.redweek.com/posting/R1518310 Mon, 31 Aug 2026 12:40:45 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,649 ($521/night)

]]> https://www.redweek.com/posting/R1504293 Tue, 28 Jul 2026 12:50:36 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–9, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $1,632 ($326/night)

]]> https://www.redweek.com/posting/R1504396 Wed, 29 Jul 2026 20:39:59 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,794 ($685/night)

]]> https://www.redweek.com/posting/R1472273 Wed, 19 Aug 2026 08:06:50 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 4–7, 2026 (3 nights)
• Studio/1 bath, sleeps 4
• $1,647 ($549/night)

]]> https://www.redweek.com/posting/R1483220 Fri, 12 Jun 2026 17:08:39 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1515844 Mon, 31 Aug 2026 06:26:05 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1520468 Wed, 02 Sep 2026 12:54:19 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1520470 Wed, 02 Sep 2026 12:51:04 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1505903 Mon, 03 Aug 2026 23:06:10 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1524048 Thu, 10 Sep 2026 19:13:30 -0700 Verified & Protected

Maui Beach Vacation Club

Kihei, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,650 ($236/night)

]]> https://www.redweek.com/posting/R1502247 Fri, 24 Jul 2026 13:04:05 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–7, 2026 (3 nights)
• Studio/1 bath, sleeps 4
• $832 ($278/night)

]]> https://www.redweek.com/posting/R1525608 Tue, 15 Sep 2026 09:09:26 -0700 Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,802 ($543/night)

]]> https://www.redweek.com/posting/R1525212 Mon, 14 Sep 2026 11:10:19 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 4–11, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $2,894 ($413/night)

]]> https://www.redweek.com/posting/R1523315 Wed, 09 Sep 2026 12:11:00 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,579 ($940/night)

]]> https://www.redweek.com/posting/R1517147 Wed, 26 Aug 2026 07:01:10 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1516226 Mon, 24 Aug 2026 12:28:37 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1517742 Fri, 28 Aug 2026 13:18:57 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1520473 Wed, 02 Sep 2026 12:47:33 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,268 ($467/night)

]]> https://www.redweek.com/posting/R1521047 Fri, 04 Sep 2026 12:42:41 -0700 Verified & Protected

Sheraton Kauai Resort Villas

Koloa, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1519934 Wed, 02 Sep 2026 19:58:41 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,649 ($521/night)

]]> https://www.redweek.com/posting/R1494875 Wed, 08 Jul 2026 11:01:45 -0700 Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/2 bath, sleeps 6
• $1,742 ($249/night)

]]> https://www.redweek.com/posting/R1520303 Thu, 03 Sep 2026 12:18:38 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,473 ($782/night)

]]> https://www.redweek.com/posting/R1513734 Wed, 19 Aug 2026 09:56:16 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1521055 Mon, 07 Sep 2026 08:35:06 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1490892 Wed, 01 Jul 2026 13:29:15 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1515995 Tue, 25 Aug 2026 10:13:35 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1505894 Mon, 03 Aug 2026 23:05:28 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1510065 Tue, 11 Aug 2026 23:12:20 -0700