https://www.redweek.com/featured/flexible-rentals/North+America/United+States/Hawaii en Mon, 10 Aug 2026 12:22:46 -0700 3600

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

• Oct 9–16, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1509836 Sun, 09 Aug 2026 14:54:30 -0700 Voted Top Pick 2026

Hyatt Vacation Club at Ka'anapali Beach

Lahaina, Hawaii

• Feb 6–13, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,031 ($576/night)

]]> https://www.redweek.com/posting/R1509655 Sun, 09 Aug 2026 07:26:29 -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 ($854/night)

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

Hyatt Vacation Club at Ka'anapali Beach

Lahaina, Hawaii

• Mar 27 – Apr 3, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1508376 Fri, 07 Aug 2026 13:17:57 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka'anapali Beach

Lahaina, Hawaii

• Apr 3–10, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1508377 Fri, 07 Aug 2026 13:17:46 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Feb 14–21, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1509076 Fri, 07 Aug 2026 10:52:18 -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 ($1,094/night)

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

The Modern Honolulu

Honolulu, Hawaii

• Nov 14–19, 2026 (5 nights)
• 1 bed/1 bath, sleeps 2
• $1,324 ($265/night)

]]> https://www.redweek.com/posting/R1508332 Fri, 07 Aug 2026 01:12:49 -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
• $4,314 ($863/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 North

Lahaina, Hawaii

• Dec 11–18, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1499094 Thu, 06 Aug 2026 13:31:02 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Feb 20–27, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $8,800 ($1,257/night)

]]> https://www.redweek.com/posting/R1508117 Thu, 06 Aug 2026 05:47:19 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka'anapali Beach

Lahaina, Hawaii

• Apr 3–10, 2027 (7 nights)
• 3 bed/3 bath, sleeps 10
• $8,418 ($1,203/night)

]]> https://www.redweek.com/posting/R1507409 Tue, 04 Aug 2026 22:01:46 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Feb 5–12, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1507448 Tue, 04 Aug 2026 09:39:36 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 27, 2026 – Jan 3, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1506246 Tue, 04 Aug 2026 01:31:42 -0700 Verified & Protected

Sheraton Kauai Resort Villas

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,358 ($765/night)

]]> https://www.redweek.com/posting/R1506222 Mon, 03 Aug 2026 23:50:13 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

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

]]> https://www.redweek.com/posting/R1506728 Mon, 03 Aug 2026 17:11:18 -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 ($581/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

• Feb 28 – Mar 7, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1505489 Sun, 02 Aug 2026 23:04:01 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Jun 26 – Jul 3, 2027 (7 nights)
• 3 bed/2.5 bath, sleeps 8
• $11,462 ($1,637/night)

]]> https://www.redweek.com/posting/R1500012 Sun, 02 Aug 2026 22:17:53 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Nov 21–27, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $4,276 ($713/night)

]]> https://www.redweek.com/posting/R1504553 Wed, 29 Jul 2026 20:51:45 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Jan 9–22, 2027 (13 nights)
• 1 bed/1 bath, sleeps 4
• $8,881 ($683/night)

]]> https://www.redweek.com/posting/R1503217 Wed, 29 Jul 2026 18:06:05 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jan 22–29, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,031 ($576/night)

]]> https://www.redweek.com/posting/R1503230 Wed, 29 Jul 2026 17:59:56 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jan 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,984 ($712/night)

]]> https://www.redweek.com/posting/R1502626 Mon, 27 Jul 2026 10:08:56 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jan 2–9, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,145 ($592/night)

]]> https://www.redweek.com/posting/R1502628 Mon, 27 Jul 2026 09:28:38 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jan 2–9, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1502630 Mon, 27 Jul 2026 09:18:36 -0700 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jul 3–8, 2028 (5 nights)
• 1 bed/1 bath, sleeps 4
• $5,202 ($1,040/night)

]]> https://www.redweek.com/posting/R1502744 Sat, 25 Jul 2026 02:39:24 -0700 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jul 1–7, 2028 (6 nights)
• 1 bed/1 bath, sleeps 4
• $6,238 ($1,040/night)

]]> https://www.redweek.com/posting/R1502742 Sat, 25 Jul 2026 02:33:15 -0700 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jul 1–7, 2027 (6 nights)
• 2 bed/2 bath, sleeps 6
• $6,565 ($1,094/night)

]]> https://www.redweek.com/posting/R1502740 Sat, 25 Jul 2026 01:47:19 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Nov 14–20, 2026 (6 nights)
• 2 bed/3 bath, sleeps 8
• $4,930 ($822/night)

]]> https://www.redweek.com/posting/R1502488 Fri, 24 Jul 2026 12:06:53 -0700 Verified & Protected

Sheraton Kauai Resort Villas

Koloa, Hawaii

• Feb 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1502132 Fri, 24 Jul 2026 09:39:50 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Nov 26 – Dec 3, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1502180 Thu, 23 Jul 2026 17:48:32 -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 ($829/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 ($618/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 ($471/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 ($471/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 ($423/night)

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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Jun 8–12, 2027 (4 nights)
• Studio/1 bath, sleeps 4
• $1,242 ($310/night)

]]> https://www.redweek.com/posting/R1499964 Thu, 23 Jul 2026 10:18:08 -0700 Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Jul 22–26, 2027 (4 nights)
• Studio/1 bath, sleeps 4
• $1,242 ($310/night)

]]> https://www.redweek.com/posting/R1499966 Wed, 22 Jul 2026 19:56:08 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Aug 6–10, 2027 (4 nights)
• 1 bed/1 bath, sleeps 4
• $2,205 ($551/night)

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

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Nov 21–28, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,802 ($543/night)

]]> https://www.redweek.com/posting/R1501629 Wed, 22 Jul 2026 14:01:57 -0700 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,924 ($418/night)

]]> https://www.redweek.com/posting/R1501286 Wed, 22 Jul 2026 12:06:54 -0700 Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Mar 30 – Apr 3, 2027 (4 nights)
• 1 bed/1 bath, sleeps 4
• $1,550 ($388/night)

]]> https://www.redweek.com/posting/R1499963 Wed, 22 Jul 2026 08:20:03 -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 ($374/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

• Dec 14–21, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $8,792 ($1,256/night)

]]> https://www.redweek.com/posting/R1500524 Tue, 21 Jul 2026 12:57:43 -0700 Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 30, 2026 – Jan 3, 2027 (4 nights)
• 1 bed/1 bath, sleeps 6
• $2,423 ($606/night)

]]> https://www.redweek.com/posting/R1499962 Tue, 21 Jul 2026 07:48:45 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,884 ($983/night)

]]> https://www.redweek.com/posting/R1500170 Tue, 21 Jul 2026 06:59:30 -0700 Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

• Nov 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,328 ($761/night)

]]> https://www.redweek.com/posting/R1496729 Tue, 21 Jul 2026 06:25:44 -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 ($985/night)

]]> https://www.redweek.com/posting/R1500650 Tue, 21 Jul 2026 05:08:25 -0700