https://www.redweek.com/featured/flexible-rentals/North+America/United+States/Hawaii en Mon, 05 Oct 2026 11:55:58 -0700 3600 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 6–13, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,129 ($800/night)

]]> https://www.redweek.com/posting/R1533922 Mon, 05 Oct 2026 08:10:12 -0700

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

• Mar 5–12, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,603 ($600/night)

]]> https://www.redweek.com/posting/R1533569 Sun, 04 Oct 2026 10:42:04 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jun 27 – Jul 2, 2027 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,750 ($500/night)

]]> https://www.redweek.com/posting/R1532746 Thu, 01 Oct 2026 22:37:23 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jun 27 – Jul 4, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,510 ($850/night)

]]> https://www.redweek.com/posting/R1532747 Thu, 01 Oct 2026 22:37:23 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• May 30 – Jun 4, 2027 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,750 ($500/night)

]]> https://www.redweek.com/posting/R1532745 Thu, 01 Oct 2026 22:37:23 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• May 23–28, 2027 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,750 ($500/night)

]]> https://www.redweek.com/posting/R1532744 Thu, 01 Oct 2026 22:31:49 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jan 9–16, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,503 ($849/night)

]]> https://www.redweek.com/posting/R1532732 Thu, 01 Oct 2026 20:27:51 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Aug 1–7, 2027 (6 nights)
• 1 bed/1 bath, sleeps 4
• $3,132 ($475/night)

]]> https://www.redweek.com/posting/R1532715 Thu, 01 Oct 2026 19:10:01 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Aug 7–13, 2027 (6 nights)
• 1 bed/1 bath, sleeps 4
• $3,132 ($475/night)

]]> https://www.redweek.com/posting/R1532723 Thu, 01 Oct 2026 19:10:01 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Apr 2–9, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,573 ($465/night)

]]> https://www.redweek.com/posting/R1532707 Thu, 01 Oct 2026 19:10:01 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 28 – Apr 4, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,984 ($650/night)

]]> https://www.redweek.com/posting/R1532468 Thu, 01 Oct 2026 11:14:11 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Jan 16–23, 2027 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,840 ($500/night)

]]> https://www.redweek.com/posting/R1532445 Thu, 01 Oct 2026 10:54:34 -0700 Verified & Protected

The Point at Poipu

Koloa, Hawaii

• Dec 27, 2026 – Jan 3, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($450/night)

]]> https://www.redweek.com/posting/R1532359 Thu, 01 Oct 2026 08:29:19 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• May 16–23, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,748 ($750/night)

]]> https://www.redweek.com/posting/R1532316 Thu, 01 Oct 2026 07:29:35 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Sep 5–9, 2027 (4 nights)
• 2 bed/2 bath, sleeps 8
• $2,205 ($500/night)

]]> https://www.redweek.com/posting/R1531754 Wed, 30 Sep 2026 05:03:27 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Jan 16–23, 2027 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,497 ($455/night)

]]> https://www.redweek.com/posting/R1531655 Tue, 29 Sep 2026 16:51:51 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Feb 7–14, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,336 ($565/night)

]]> https://www.redweek.com/posting/R1531289 Mon, 28 Sep 2026 20:17:22 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Mar 5–12, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $4,222 ($550/night)

]]> https://www.redweek.com/posting/R1531187 Mon, 28 Sep 2026 15:01:15 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Jan 16–23, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,984 ($650/night)

]]> https://www.redweek.com/posting/R1530903 Mon, 28 Sep 2026 05:52:45 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Mar 28 – Apr 4, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,748 ($750/night)

]]> https://www.redweek.com/posting/R1530386 Sat, 26 Sep 2026 11:59:32 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 22–26, 2027 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,682 ($380/night)

]]> https://www.redweek.com/posting/R1530090 Fri, 25 Sep 2026 12:24:23 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 16–23, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,282 ($689/night)

]]> https://www.redweek.com/posting/R1529360 Wed, 23 Sep 2026 13:53:42 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jun 20–27, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,137 ($670/night)

]]> https://www.redweek.com/posting/R1529358 Wed, 23 Sep 2026 13:50:43 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka'anapali Beach

Lahaina, Hawaii

• Feb 27 – Mar 6, 2027 (7 nights)
• 3 bed/3 bath, sleeps 10
• $13,759 ($1,800/night)

]]> https://www.redweek.com/posting/R1528809 Tue, 22 Sep 2026 11:07:25 -0700 Verified & Protected

Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

• Mar 27 – Apr 4, 2027 (8 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($350/night)

]]> https://www.redweek.com/posting/R1528737 Tue, 22 Sep 2026 09:40:23 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Mar 6–13, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,222 ($550/night)

]]> https://www.redweek.com/posting/R1528441 Mon, 21 Sep 2026 15:07:31 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jan 1–8, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,268 ($425/night)

]]> https://www.redweek.com/posting/R1527639 Sat, 19 Sep 2026 10:04:08 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• May 30 – Jun 6, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($700/night)

]]> https://www.redweek.com/posting/R1527372 Fri, 18 Sep 2026 20:01:07 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Jul 3–10, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,069 ($530/night)

]]> https://www.redweek.com/posting/R1527013 Fri, 18 Sep 2026 07:12:18 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Apr 6–13, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,984 ($650/night)

]]> https://www.redweek.com/posting/R1523993 Fri, 11 Sep 2026 10:48:18 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Jan 9–16, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($500/night)

]]> https://www.redweek.com/posting/R1523950 Thu, 10 Sep 2026 14:43:33 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Feb 14–21, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $2,886 ($375/night)

]]> https://www.redweek.com/posting/R1523477 Thu, 10 Sep 2026 12:25:17 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Feb 14–21, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($700/night)

]]> https://www.redweek.com/posting/R1522951 Thu, 10 Sep 2026 10:45:42 -0700 Verified & Protected

The Point at Poipu

Koloa, Hawaii

• Jan 15–22, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,687 ($480/night)

]]> https://www.redweek.com/posting/R1523716 Thu, 10 Sep 2026 07:18:27 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jul 2–9, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,924 ($380/night)

]]> https://www.redweek.com/posting/R1522443 Tue, 08 Sep 2026 13:44:15 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jul 2–9, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,458 ($450/night)

]]> https://www.redweek.com/posting/R1522456 Tue, 08 Sep 2026 13:42:41 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Mar 29 – Apr 5, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,200 ($285/night)

]]> https://www.redweek.com/posting/R1522433 Tue, 08 Sep 2026 11:55:02 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jan 9–15, 2027 (6 nights)
• Studio/1 bath, sleeps 4
• $2,314 ($350/night)

]]> https://www.redweek.com/posting/R1522567 Tue, 08 Sep 2026 11:21:46 -0700 Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Jan 8–15, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($700/night)

]]> https://www.redweek.com/posting/R1522602 Tue, 08 Sep 2026 05:16:18 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jul 31 – Aug 7, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,884 ($899/night)

]]> https://www.redweek.com/posting/R1521510 Mon, 07 Sep 2026 09:47:47 -0700 Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

• Jan 10–15, 2027 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,932 ($350/night)

]]> https://www.redweek.com/posting/R1519652 Fri, 04 Sep 2026 14:13:59 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Mar 13–20, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,649 ($475/night)

]]> https://www.redweek.com/posting/R1521346 Fri, 04 Sep 2026 12:32:42 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 28 – Apr 4, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $2,505 ($325/night)

]]> https://www.redweek.com/posting/R1520882 Thu, 03 Sep 2026 10:55:02 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Feb 26 – Mar 5, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,091 ($664/night)

]]> https://www.redweek.com/posting/R1519948 Wed, 02 Sep 2026 20:08:35 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Feb 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,222 ($550/night)

]]> https://www.redweek.com/posting/R1517803 Tue, 01 Sep 2026 14:04:36 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Jul 9–16, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,671 ($740/night)

]]> https://www.redweek.com/posting/R1519663 Tue, 01 Sep 2026 12:29:12 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jun 5–12, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,121 ($799/night)

]]> https://www.redweek.com/posting/R1519746 Tue, 01 Sep 2026 09:49:34 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Feb 12–19, 2027 (7 nights)
• 1 bed/2 bath, sleeps 4
• $4,565 ($595/night)

]]> https://www.redweek.com/posting/R1518908 Tue, 01 Sep 2026 08:30:21 -0700