https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii en Sat, 06 Jun 2026 00:00:54 -0700 3600 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 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 Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1446056 Tue, 24 Mar 2026 09:06:52 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $2,968 ($495/night)

]]> https://www.redweek.com/posting/R1437659 Wed, 25 Feb 2026 10:15:08 -0800 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 Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $10,489 ($1,498/night)

]]> https://www.redweek.com/posting/R1411325 Wed, 07 Jan 2026 07:53:14 -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 8
• $6,669 ($953/night)

]]> https://www.redweek.com/posting/R1454724 Tue, 31 Mar 2026 10:57:11 -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
• $5,671 ($810/night)

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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,314 ($331/night)

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

Imperial Hawaii Vacation Club

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/2 bath, sleeps 6
• $1,649 ($236/night)

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

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

• Dec 2–7, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,987 ($397/night)

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

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 3–10, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,451 ($493/night)

]]> https://www.redweek.com/posting/R1456697 Tue, 07 Apr 2026 06:42:40 -0700 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

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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $2,586 ($370/night)

]]> https://www.redweek.com/posting/R1463761 Thu, 23 Apr 2026 09:51:01 -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
• $4,440 ($634/night)

]]> https://www.redweek.com/posting/R1462513 Fri, 08 May 2026 06:09:22 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1435025 Wed, 18 Feb 2026 12:34:15 -0800 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
• $3,022 ($432/night)

]]> https://www.redweek.com/posting/R1417211 Mon, 19 Jan 2026 06:31:51 -0800 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1463508 Thu, 23 Apr 2026 11:35:56 -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 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

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

]]> https://www.redweek.com/posting/R1402512 Fri, 12 Dec 2025 08:44:19 -0800 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,548 ($650/night)

]]> https://www.redweek.com/posting/R1466454 Tue, 28 Apr 2026 14:24:43 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $6,121 ($874/night)

]]> https://www.redweek.com/posting/R1465535 Tue, 28 Apr 2026 08:22:26 -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
• $2,914 ($416/night)

]]> https://www.redweek.com/posting/R1477037 Wed, 27 May 2026 11:43:56 -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
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1442492 Mon, 16 Mar 2026 18:47:39 -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
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1459563 Mon, 13 Apr 2026 11:17:52 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1410436 Tue, 06 Jan 2026 08:10:12 -0800 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,911 ($844/night)

]]> https://www.redweek.com/posting/R1470827 Sat, 09 May 2026 08:05:43 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,450 ($636/night)

]]> https://www.redweek.com/posting/R1420240 Tue, 20 Jan 2026 15:37:56 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1358773 Thu, 06 Nov 2025 16:08:13 -0800 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
• $4,602 ($657/night)

]]> https://www.redweek.com/posting/R1480112 Thu, 04 Jun 2026 12:18:30 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,306 ($472/night)

]]> https://www.redweek.com/posting/R1476397 Mon, 25 May 2026 18:38:16 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1416315 Thu, 29 Jan 2026 09:12:28 -0800 Verified & Protected

One Napili Way

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 3 bed/2 bath, sleeps 6
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1463970 Mon, 27 Apr 2026 17:09:10 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–14, 2026 (9 nights)
• 2 bed/2 bath, sleeps 8
• $7,088 ($788/night)

]]> https://www.redweek.com/posting/R1447967 Thu, 19 Mar 2026 08:04:52 -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
• $4,832 ($690/night)

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

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,039 ($720/night)

]]> https://www.redweek.com/posting/R1412136 Sun, 04 Jan 2026 15:49:39 -0800 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1479883 Thu, 04 Jun 2026 03:29:55 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $10,925 ($1,561/night)

]]> https://www.redweek.com/posting/R1423906 Thu, 29 Jan 2026 13:16:31 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,112 ($588/night)

]]> https://www.redweek.com/posting/R1455028 Tue, 14 Apr 2026 14:11:51 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1425587 Tue, 17 Feb 2026 15:11:53 -0800 Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $8,745 ($1,249/night)

]]> https://www.redweek.com/posting/R1432206 Wed, 22 Apr 2026 14:17:30 -0700 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 5–12, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $4,930 ($704/night)

]]> https://www.redweek.com/posting/R1469454 Mon, 01 Jun 2026 15:07:51 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

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

]]> https://www.redweek.com/posting/R1477653 Fri, 29 May 2026 06:07:17 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,020 ($860/night)

]]> https://www.redweek.com/posting/R1433967 Wed, 06 May 2026 15:08:59 -0700