https://www.redweek.com/featured/flexible-rentals/North+America/United+States/Hawaii en Sat, 25 Apr 2026 11:30:19 -0700 3600 Verified & Protected

Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

• Aug 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,091 ($299/night)

]]> https://www.redweek.com/posting/R1463407 Fri, 24 Apr 2026 16:58:35 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Sep 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,020 ($860/night)

]]> https://www.redweek.com/posting/R1453842 Fri, 24 Apr 2026 13:08:51 -0700

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Sep 7–12, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $3,568 ($714/night)

]]> https://www.redweek.com/posting/R1465071 Fri, 24 Apr 2026 11:11:26 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Sep 6–13, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $3,948 ($564/night)

]]> https://www.redweek.com/posting/R1464844 Fri, 24 Apr 2026 10:54:03 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Oct 10–17, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,679 ($668/night)

]]> https://www.redweek.com/posting/R1464828 Fri, 24 Apr 2026 09:34:46 -0700 Verified & Protected

Kahana Beach Resort

Lahaina, Hawaii

• Jul 15–22, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $1,512 ($216/night)

]]> https://www.redweek.com/posting/R1464094 Fri, 24 Apr 2026 07:29:51 -0700 Verified & Protected

Kahana Beach Resort

Lahaina, Hawaii

• Jul 15–22, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $1,512 ($216/night)

]]> https://www.redweek.com/posting/R1464095 Fri, 24 Apr 2026 07:27:20 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 13–20, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $5,148 ($735/night)

]]> https://www.redweek.com/posting/R1464545 Fri, 24 Apr 2026 06:36:53 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jul 25 – Aug 1, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,531 ($362/night)

]]> https://www.redweek.com/posting/R1464877 Thu, 23 Apr 2026 21:19:42 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jul 18–25, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,531 ($362/night)

]]> https://www.redweek.com/posting/R1464875 Thu, 23 Apr 2026 21:07:36 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jul 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,948 ($564/night)

]]> https://www.redweek.com/posting/R1464819 Thu, 23 Apr 2026 16:32:30 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Aug 1–8, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $5,061 ($723/night)

]]> https://www.redweek.com/posting/R1464417 Thu, 23 Apr 2026 13:57:12 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Aug 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,527 ($647/night)

]]> https://www.redweek.com/posting/R1463933 Thu, 23 Apr 2026 12:37:10 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Aug 30 – Sep 6, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,528 ($361/night)

]]> https://www.redweek.com/posting/R1463784 Thu, 23 Apr 2026 09:35:02 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,328 ($1,047/night)

]]> https://www.redweek.com/posting/R1464068 Thu, 23 Apr 2026 08:48:34 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 12–19, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,404 ($486/night)

]]> https://www.redweek.com/posting/R1464057 Thu, 23 Apr 2026 08:37:27 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jan 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,110 ($1,016/night)

]]> https://www.redweek.com/posting/R1463270 Thu, 23 Apr 2026 07:22:59 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Apr 3–10, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,622 ($517/night)

]]> https://www.redweek.com/posting/R1464320 Wed, 22 Apr 2026 15:20:31 -0700 Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

• Jul 18–25, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1462748 Wed, 22 Apr 2026 15:18:06 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Jan 9 – Feb 6, 2027 (28 nights)
• 3 bed/2.5 bath, sleeps 8
• $26,883 ($960/night)

]]> https://www.redweek.com/posting/R1461399 Wed, 22 Apr 2026 12:02:56 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Apr 3–10, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,328 ($1,047/night)

]]> https://www.redweek.com/posting/R1464074 Wed, 22 Apr 2026 09:52:59 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1463716 Wed, 22 Apr 2026 06:45:28 -0700 Verified & Protected

Sands of Kahana Vacation Club

Lahaina, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,835 ($548/night)

]]> https://www.redweek.com/posting/R1441243 Tue, 21 Apr 2026 16:08:40 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 7–14, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,611 ($516/night)

]]> https://www.redweek.com/posting/R1462726 Mon, 20 Apr 2026 14:26:54 -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
• $3,611 ($516/night)

]]> https://www.redweek.com/posting/R1462728 Mon, 20 Apr 2026 14:24:57 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 6–13, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,611 ($516/night)

]]> https://www.redweek.com/posting/R1462722 Mon, 20 Apr 2026 14:23:32 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 5–12, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,611 ($516/night)

]]> https://www.redweek.com/posting/R1462721 Mon, 20 Apr 2026 14:20:35 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Oct 17–22, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,478 ($496/night)

]]> https://www.redweek.com/posting/R1463162 Mon, 20 Apr 2026 13:50:24 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Jul 31 – Aug 7, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,230 ($461/night)

]]> https://www.redweek.com/posting/R1460186 Mon, 20 Apr 2026 11:58:30 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Mar 21–28, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $6,347 ($907/night)

]]> https://www.redweek.com/posting/R1459432 Mon, 20 Apr 2026 09:48:28 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Mar 14–21, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $6,292 ($899/night)

]]> https://www.redweek.com/posting/R1459437 Mon, 20 Apr 2026 09:47:55 -0700 Verified & Protected

The Gardens at West Maui

Kapalua, Hawaii

• Sep 12–19, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,605 ($229/night)

]]> https://www.redweek.com/posting/R1457130 Fri, 17 Apr 2026 13:48:36 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Oct 10–17, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $6,565 ($938/night)

]]> https://www.redweek.com/posting/R1462005 Fri, 17 Apr 2026 11:59:18 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 6–13, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1462181 Fri, 17 Apr 2026 11:48:39 -0700 Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

• Aug 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1458256 Thu, 16 Apr 2026 19:23:39 -0700 Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Sep 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1461868 Thu, 16 Apr 2026 10:51:54 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Mar 20–27, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,929 ($704/night)

]]> https://www.redweek.com/posting/R1451008 Thu, 16 Apr 2026 10:29:58 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Sep 6–13, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,949 ($564/night)

]]> https://www.redweek.com/posting/R1442267 Thu, 16 Apr 2026 06:41:20 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Mar 27 – Apr 3, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,911 ($844/night)

]]> https://www.redweek.com/posting/R1455472 Wed, 15 Apr 2026 09:16:36 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Jan 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $6,045 ($864/night)

]]> https://www.redweek.com/posting/R1460674 Wed, 15 Apr 2026 05:57:01 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jan 10–17, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,140 ($591/night)

]]> https://www.redweek.com/posting/R1457895 Mon, 13 Apr 2026 09:46:19 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Aug 8–15, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $6,565 ($938/night)

]]> https://www.redweek.com/posting/R1458698 Mon, 13 Apr 2026 08:19:04 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Sep 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,731 ($533/night)

]]> https://www.redweek.com/posting/R1454964 Fri, 10 Apr 2026 12:25:58 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Oct 8–12, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $3,295 ($824/night)

]]> https://www.redweek.com/posting/R1441257 Fri, 10 Apr 2026 12:12:55 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Feb 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,977 ($711/night)

]]> https://www.redweek.com/posting/R1458427 Fri, 10 Apr 2026 08:38:08 -0700 Verified & Protected

Kahana Beach Resort

Lahaina, Hawaii

• Mar 21–28, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $1,512 ($216/night)

]]> https://www.redweek.com/posting/R1453582 Thu, 09 Apr 2026 15:27:16 -0700 Verified & Protected

Kahana Beach Resort

Lahaina, Hawaii

• Mar 17–24, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $1,512 ($216/night)

]]> https://www.redweek.com/posting/R1453581 Thu, 09 Apr 2026 15:25:03 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 15–22, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,468 ($495/night)

]]> https://www.redweek.com/posting/R1455541 Thu, 09 Apr 2026 14:34:36 -0700