https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii en Mon, 27 Jul 2026 05:21:56 -0700 3600 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 Sun, 26 Jul 2026 16:23:12 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $2,804 ($467/night)

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

Club Wyndham Bali Hai Villas

Princeville, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1493960 Mon, 06 Jul 2026 09:50:31 -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 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 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 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 1–7, 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

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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,260 ($323/night)

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

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

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

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 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 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,886 ($412/night)

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

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 4–7, 2026 (3 nights)
• Studio/1 bath, sleeps 4
• $1,620 ($540/night)

]]> https://www.redweek.com/posting/R1483219 Fri, 12 Jun 2026 17:08:39 -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
• $3,954 ($565/night)

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

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 North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,295 ($471/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
• $6,121 ($874/night)

]]> https://www.redweek.com/posting/R1465535 Tue, 28 Apr 2026 08:22:26 -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
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1493360 Tue, 07 Jul 2026 10:54:48 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,153 ($450/night)

]]> https://www.redweek.com/posting/R1502557 Fri, 24 Jul 2026 13:39:29 -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
• $4,112 ($588/night)

]]> https://www.redweek.com/posting/R1490892 Wed, 01 Jul 2026 13:29:15 -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
• $3,230 ($461/night)

]]> https://www.redweek.com/posting/R1442492 Mon, 16 Mar 2026 18:47:39 -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

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 Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $9,143 ($1,306/night)

]]> https://www.redweek.com/posting/R1495958 Fri, 10 Jul 2026 12:13:37 -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
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1358217 Wed, 05 Nov 2025 12:06:58 -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
• $4,527 ($647/night)

]]> https://www.redweek.com/posting/R1493547 Mon, 13 Jul 2026 09:57:04 -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
• $3,622 ($517/night)

]]> https://www.redweek.com/posting/R1467286 Thu, 30 Apr 2026 16:51:12 -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
• $4,167 ($595/night)

]]> https://www.redweek.com/posting/R1453418 Mon, 30 Mar 2026 04:13:34 -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
• $5,252 ($750/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
• $4,374 ($625/night)

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

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 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

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 5–12, 2026 (7 nights)
• Studio/1 bath, sleeps 3
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1480691 Tue, 09 Jun 2026 13:29:21 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,137 ($734/night)

]]> https://www.redweek.com/posting/R1494249 Wed, 08 Jul 2026 11:20:17 -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

Pono Kai

Kapaa, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,772 ($253/night)

]]> https://www.redweek.com/posting/R1491192 Wed, 08 Jul 2026 11:24:27 -0700 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,987 ($284/night)

]]> https://www.redweek.com/posting/R1432253 Mon, 09 Mar 2026 11:21:09 -0700