https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii en Tue, 05 May 2026 09:02:08 -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
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1403989 Tue, 16 Dec 2025 07:10:44 -0800 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 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)
• 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 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 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)
• 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

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 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 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

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 3–10, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,382 ($483/night)

]]> https://www.redweek.com/posting/R1460980 Tue, 21 Apr 2026 10:38:20 -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)
• 2 bed/2 bath, sleeps 8
• $4,658 ($665/night)

]]> https://www.redweek.com/posting/R1466454 Tue, 28 Apr 2026 14:24:43 -0700 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 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
• $6,888 ($984/night)

]]> https://www.redweek.com/posting/R1465535 Tue, 28 Apr 2026 08:22:26 -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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1463761 Thu, 23 Apr 2026 09:51:01 -0700 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 Sat, 18 Apr 2026 04:53:28 -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
• $3,295 ($471/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 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

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 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

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 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

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 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

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

]]> https://www.redweek.com/posting/R1433967 Mon, 16 Feb 2026 06:40:49 -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

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 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

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 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

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,510 ($930/night)

]]> https://www.redweek.com/posting/R1436563 Mon, 23 Feb 2026 07:05:02 -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 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/R1465348 Tue, 28 Apr 2026 07:37:16 -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 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

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 Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

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

]]> https://www.redweek.com/posting/R1466996 Wed, 29 Apr 2026 13:10:41 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $7,382 ($1,055/night)

]]> https://www.redweek.com/posting/R1467095 Wed, 29 Apr 2026 18:01:38 -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 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 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 Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

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

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

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1463764 Thu, 23 Apr 2026 09:49:08 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $8,636 ($1,234/night)

]]> https://www.redweek.com/posting/R1459507 Wed, 15 Apr 2026 06:17:10 -0700