https://www.redweek.com/featured/fall-rentals/North+America/United+States/Hawaii en Thu, 08 Oct 2026 22:14:37 -0700 3600 Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

• Oct 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,204 ($155/night)

]]> https://www.redweek.com/posting/R1527153 Fri, 18 Sep 2026 11:28:11 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Oct 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,402 ($836/night)

]]> https://www.redweek.com/posting/R1475485 Fri, 22 May 2026 10:25:41 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,222 ($550/night)

]]> https://www.redweek.com/posting/R1509225 Fri, 07 Aug 2026 16:13:20 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,069 ($399/night)

]]> https://www.redweek.com/posting/R1533089 Fri, 02 Oct 2026 16:02:26 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Oct 17–24, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $10,108 ($1,321/night)

]]> https://www.redweek.com/posting/R1409246 Mon, 29 Dec 2025 19:26:41 -0800 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Oct 17–24, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,130 ($407/night)

]]> https://www.redweek.com/posting/R1514391 Wed, 19 Aug 2026 15:08:59 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,390 ($310/night)

]]> https://www.redweek.com/posting/R1509268 Mon, 10 Aug 2026 11:06:44 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,541 ($985/night)

]]> https://www.redweek.com/posting/R1393772 Wed, 26 Nov 2025 19:24:57 -0800 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,993 ($389/night)

]]> https://www.redweek.com/posting/R1495915 Thu, 16 Jul 2026 19:36:16 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,603 ($600/night)

]]> https://www.redweek.com/posting/R1475376 Fri, 22 May 2026 07:44:14 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,238 ($814/night)

]]> https://www.redweek.com/posting/R1491007 Wed, 01 Jul 2026 12:43:25 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Oct 18–25, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $2,306 ($299/night)

]]> https://www.redweek.com/posting/R1499295 Fri, 17 Jul 2026 13:00:29 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,458 ($450/night)

]]> https://www.redweek.com/posting/R1352584 Wed, 22 Oct 2025 13:06:46 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Oct 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,123 ($275/night)

]]> https://www.redweek.com/posting/R1508503 Thu, 06 Aug 2026 13:53:55 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Oct 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,840 ($500/night)

]]> https://www.redweek.com/posting/R1519253 Mon, 31 Aug 2026 13:35:48 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Oct 18–25, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $6,510 ($850/night)

]]> https://www.redweek.com/posting/R1514071 Wed, 19 Aug 2026 10:56:02 -0700 Verified & Protected

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

• Oct 18–25, 2026 (7 nights)
• 3 bed/3 bath, sleeps 8
• $2,886 ($375/night)

]]> https://www.redweek.com/posting/R1508041 Fri, 07 Aug 2026 09:19:45 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,748 ($619/night)

]]> https://www.redweek.com/posting/R1516183 Mon, 24 Aug 2026 12:32:30 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Oct 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,977 ($649/night)

]]> https://www.redweek.com/posting/R1447483 Thu, 26 Mar 2026 07:56:33 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Oct 20–25, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($500/night)

]]> https://www.redweek.com/posting/R1529400 Wed, 23 Sep 2026 14:47:48 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Oct 20–27, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $5,475 ($714/night)

]]> https://www.redweek.com/posting/R1455795 Tue, 05 May 2026 13:03:00 -0700 Verified & Protected

The Whaler

Lahaina, Hawaii

• Oct 21 – Nov 4, 2026 (14 nights)
• 1 bed/2 bath, sleeps 5
• $4,527 ($295/night)

]]> https://www.redweek.com/posting/R1518524 Mon, 31 Aug 2026 12:34:17 -0700 Verified & Protected

Lawai Beach Resort

Koloa, Hawaii

• Oct 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,234 ($159/night)

]]> https://www.redweek.com/posting/R1393832 Tue, 20 Jan 2026 11:41:21 -0800 Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

• Oct 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,069 ($399/night)

]]> https://www.redweek.com/posting/R1511591 Thu, 13 Aug 2026 06:19:01 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,603 ($600/night)

]]> https://www.redweek.com/posting/R1475377 Fri, 22 May 2026 07:51:58 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Oct 23–30, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,603 ($600/night)

]]> https://www.redweek.com/posting/R1508249 Thu, 06 Aug 2026 11:52:21 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Oct 23–30, 2026 (7 nights)
• 3 bed/2.5 bath, sleeps 8
• $6,701 ($875/night)

]]> https://www.redweek.com/posting/R1529434 Wed, 23 Sep 2026 16:18:07 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 23–30, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,794 ($625/night)

]]> https://www.redweek.com/posting/R1488276 Thu, 25 Jun 2026 07:31:13 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Oct 23–30, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $4,382 ($571/night)

]]> https://www.redweek.com/posting/R1501384 Wed, 22 Jul 2026 07:47:09 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Oct 23–30, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $1,550 ($200/night)

]]> https://www.redweek.com/posting/R1519605 Tue, 01 Sep 2026 07:52:28 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Oct 23–30, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $4,603 ($600/night)

]]> https://www.redweek.com/posting/R1488335 Thu, 25 Jun 2026 07:51:09 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Oct 23–28, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $2,423 ($440/night)

]]> https://www.redweek.com/posting/R1521128 Fri, 04 Sep 2026 06:35:54 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Oct 23–30, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,077 ($400/night)

]]> https://www.redweek.com/posting/R1469250 Thu, 07 May 2026 11:11:19 -0700 Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

• Oct 23–30, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1533936 Mon, 05 Oct 2026 08:29:27 -0700 Verified & Protected

Club Wyndham Ka 'Eo Kai

Princeville, Hawaii

• Oct 23 – Nov 1, 2026 (9 nights)
• 1 bed/1 bath, sleeps 4
• $2,840 ($287/night)

]]> https://www.redweek.com/posting/R1512242 Mon, 24 Aug 2026 10:45:07 -0700 Verified & Protected

Hokulani Waikiki by Hilton Grand Vacations

Honolulu, Hawaii

• Oct 24–31, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,010 ($130/night)

]]> https://www.redweek.com/posting/R1463891 Mon, 27 Apr 2026 15:02:25 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,031 ($525/night)

]]> https://www.redweek.com/posting/R1523435 Wed, 09 Sep 2026 13:06:40 -0700 Verified & Protected

Hono Koa Resort

Honokowai, Hawaii

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,465 ($189/night)

]]> https://www.redweek.com/posting/R1531236 Mon, 28 Sep 2026 17:21:17 -0700 Verified & Protected

Hokulani Waikiki by Hilton Grand Vacations

Honolulu, Hawaii

• Oct 24–31, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,704 ($220/night)

]]> https://www.redweek.com/posting/R1447364 Tue, 07 Apr 2026 07:04:11 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,213 ($680/night)

]]> https://www.redweek.com/posting/R1486859 Thu, 25 Jun 2026 06:38:33 -0700 Verified & Protected

Hokulani Waikiki by Hilton Grand Vacations

Honolulu, Hawaii

• Oct 24–31, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $769 ($99/night)

]]> https://www.redweek.com/posting/R1530565 Sun, 27 Sep 2026 07:14:53 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 24–31, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $1,772 ($229/night)

]]> https://www.redweek.com/posting/R1490603 Tue, 30 Jun 2026 07:11:20 -0700 Verified & Protected

Hokulani Waikiki by Hilton Grand Vacations

Honolulu, Hawaii

• Oct 24–31, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $808 ($104/night)

]]> https://www.redweek.com/posting/R1527611 Sat, 19 Sep 2026 09:32:46 -0700 Verified & Protected

Hanalei Bay Resort

Princeville, Hawaii

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,886 ($375/night)

]]> https://www.redweek.com/posting/R1523296 Wed, 09 Sep 2026 10:16:59 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Oct 24–31, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,810 ($365/night)

]]> https://www.redweek.com/posting/R1445606 Tue, 17 Mar 2026 07:19:44 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Oct 24–31, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,642 ($343/night)

]]> https://www.redweek.com/posting/R1478813 Tue, 02 Jun 2026 11:39:33 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,924 ($380/night)

]]> https://www.redweek.com/posting/R1449759 Tue, 24 Mar 2026 08:49:22 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 24–30, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $4,211 ($640/night)

]]> https://www.redweek.com/posting/R1408143 Wed, 31 Dec 2025 11:03:56 -0800