https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii?sort=date en Sun, 05 Apr 2026 13:10:00 -0700 3600 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

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 1–8, 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 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1403989 Tue, 16 Dec 2025 07:10:44 -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 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

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 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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,368 ($338/night)

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

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 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 Sat, 04 Apr 2026 12:15:26 -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
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1435025 Wed, 18 Feb 2026 12:34:15 -0800 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

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

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1417211 Mon, 19 Jan 2026 06:31:51 -0800 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

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,557 ($794/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)
• 2 bed/2 bath, sleeps 8
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1358217 Wed, 05 Nov 2025 12:06:58 -0800 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
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1426045 Fri, 06 Feb 2026 09:01:46 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–11, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $4,984 ($831/night)

]]> https://www.redweek.com/posting/R1446645 Mon, 16 Mar 2026 14:30:23 -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
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1442569 Tue, 17 Mar 2026 14:24:56 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,560 ($937/night)

]]> https://www.redweek.com/posting/R1416332 Wed, 21 Jan 2026 12:45:54 -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
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1410436 Tue, 06 Jan 2026 08:10:12 -0800 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
• $5,800 ($829/night)

]]> https://www.redweek.com/posting/R1442538 Fri, 06 Mar 2026 12:01:07 -0800 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

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

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,183 ($312/night)

]]> https://www.redweek.com/posting/R1432253 Mon, 09 Mar 2026 11:21:09 -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
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1358773 Thu, 06 Nov 2025 16:08:13 -0800 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
• $5,748 ($821/night)

]]> https://www.redweek.com/posting/R1424614 Thu, 29 Jan 2026 14:55:40 -0800 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,330 ($619/night)

]]> https://www.redweek.com/posting/R1397420 Sat, 13 Dec 2025 07:36:05 -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

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 Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,167 ($595/night)

]]> https://www.redweek.com/posting/R1453418 Mon, 30 Mar 2026 04:13:34 -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

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/R1412130 Sun, 04 Jan 2026 15:46:57 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 5–10, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,859 ($572/night)

]]> https://www.redweek.com/posting/R1426664 Tue, 03 Feb 2026 07:00:09 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $9,835 ($1,405/night)

]]> https://www.redweek.com/posting/R1434348 Tue, 17 Feb 2026 07:18:06 -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
• $4,330 ($619/night)

]]> https://www.redweek.com/posting/R1435489 Thu, 19 Feb 2026 11:35:19 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $8,745 ($1,249/night)

]]> https://www.redweek.com/posting/R1414138 Mon, 12 Jan 2026 19:41:32 -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
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1419762 Wed, 28 Jan 2026 06:26:49 -0800 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
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1415727 Mon, 19 Jan 2026 06:53:05 -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 Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $6,107 ($872/night)

]]> https://www.redweek.com/posting/R1431658 Wed, 18 Feb 2026 08:08:06 -0800 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
• $3,073 ($439/night)

]]> https://www.redweek.com/posting/R1448730 Wed, 25 Mar 2026 06:22:45 -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

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,292 ($899/night)

]]> https://www.redweek.com/posting/R1431775 Fri, 20 Feb 2026 06:14:28 -0800 Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,676 ($525/night)

]]> https://www.redweek.com/posting/R1446258 Wed, 18 Mar 2026 11:55:14 -0700