https://www.redweek.com/featured/flexible-rentals/North+America/United+States/Hawaii/Maui/Kaanapali en Mon, 05 Oct 2026 13:58:05 -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 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 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

• 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

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 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

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 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

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

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 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

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 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 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Jan 17–24, 2027 (7 nights)
• 1 bed/2 bath, sleeps 4
• $4,222 ($550/night)

]]> https://www.redweek.com/posting/R1519252 Mon, 31 Aug 2026 13:40:06 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Jun 20–27, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,390 ($310/night)

]]> https://www.redweek.com/posting/R1516654 Fri, 28 Aug 2026 15:31:27 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Jul 2–9, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,268 ($425/night)

]]> https://www.redweek.com/posting/R1516653 Fri, 28 Aug 2026 15:23:34 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jun 12–19, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,701 ($875/night)

]]> https://www.redweek.com/posting/R1516858 Thu, 27 Aug 2026 13:38:20 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Apr 3–10, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,451 ($449/night)

]]> https://www.redweek.com/posting/R1517663 Thu, 27 Aug 2026 11:45:37 -0700 Verified & Protected

Kahana Beach Resort

Lahaina, Hawaii

• Mar 7–14, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1514750 Thu, 27 Aug 2026 11:16:30 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jan 9–16, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $2,505 ($325/night)

]]> https://www.redweek.com/posting/R1516906 Wed, 26 Aug 2026 06:49:03 -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
• $3,001 ($390/night)

]]> https://www.redweek.com/posting/R1509076 Tue, 25 Aug 2026 12:25:20 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Feb 5–12, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,191 ($415/night)

]]> https://www.redweek.com/posting/R1507448 Tue, 25 Aug 2026 11:59:01 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Aug 7–14, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,892 ($900/night)

]]> https://www.redweek.com/posting/R1516267 Mon, 24 Aug 2026 09:32:27 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Feb 12–19, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,191 ($415/night)

]]> https://www.redweek.com/posting/R1509210 Sun, 09 Aug 2026 02:13:04 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Jul 5–12, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $5,976 ($780/night)

]]> https://www.redweek.com/posting/R1508153 Fri, 07 Aug 2026 14:56:05 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Jul 17–24, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,655 ($1,000/night)

]]> https://www.redweek.com/posting/R1508129 Fri, 07 Aug 2026 07:23:17 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Mar 20–25, 2027 (5 nights)
• 2 bed/2 bath, sleeps 6
• $4,042 ($737/night)

]]> https://www.redweek.com/posting/R1508550 Thu, 06 Aug 2026 18:36:19 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Feb 20–27, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,069 ($530/night)

]]> https://www.redweek.com/posting/R1503254 Sun, 02 Aug 2026 23:04:18 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jul 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,801 ($757/night)

]]> https://www.redweek.com/posting/R1501583 Thu, 23 Jul 2026 11:40:30 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jul 3–10, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,328 ($564/night)

]]> https://www.redweek.com/posting/R1501585 Thu, 23 Jul 2026 11:39:51 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jun 5–12, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,298 ($429/night)

]]> https://www.redweek.com/posting/R1501579 Thu, 23 Jul 2026 11:39:11 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jun 5–12, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,298 ($429/night)

]]> https://www.redweek.com/posting/R1501576 Thu, 23 Jul 2026 11:38:27 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jul 9–16, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $2,963 ($385/night)

]]> https://www.redweek.com/posting/R1501588 Thu, 23 Jul 2026 11:37:29 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Aug 6–10, 2027 (4 nights)
• 1 bed/1 bath, sleeps 4
• $1,066 ($240/night)

]]> https://www.redweek.com/posting/R1499968 Wed, 22 Jul 2026 19:29:21 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Feb 27 – Mar 6, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $2,619 ($340/night)

]]> https://www.redweek.com/posting/R1500061 Tue, 21 Jul 2026 14:19:23 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Apr 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,892 ($900/night)

]]> https://www.redweek.com/posting/R1500650 Tue, 21 Jul 2026 05:08:25 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Feb 14–18, 2027 (4 nights)
• 1 bed/1 bath, sleeps 4
• $3,426 ($780/night)

]]> https://www.redweek.com/posting/R1496822 Mon, 13 Jul 2026 09:24:06 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jul 3–10, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,031 ($525/night)

]]> https://www.redweek.com/posting/R1493333 Tue, 07 Jul 2026 11:01:55 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jul 4–11, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $5,328 ($695/night)

]]> https://www.redweek.com/posting/R1493470 Tue, 07 Jul 2026 09:45:29 -0700