https://www.redweek.com/featured/flexible-rentals/North+America/United+States/Hawaii en Sun, 05 Apr 2026 13:09:47 -0700 3600 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Aug 30 – Sep 5, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $1,987 ($331/night)

]]> https://www.redweek.com/posting/R1454791 Fri, 03 Apr 2026 10:43:49 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Mar 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,930 ($704/night)

]]> https://www.redweek.com/posting/R1455298 Fri, 03 Apr 2026 08:51:55 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Jul 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,257 ($751/night)

]]> https://www.redweek.com/posting/R1431575 Fri, 03 Apr 2026 06:40:40 -0700 Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Jan 16–23, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,977 ($711/night)

]]> https://www.redweek.com/posting/R1455773 Thu, 02 Apr 2026 13:53:04 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Apr 20–27, 2027 (7 nights)
• 3 bed/3 bath, sleeps 10
• $4,930 ($704/night)

]]> https://www.redweek.com/posting/R1448358 Thu, 02 Apr 2026 11:40:31 -0700 Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Aug 28 – Sep 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1455698 Thu, 02 Apr 2026 11:24:08 -0700 Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Aug 21–28, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1455695 Thu, 02 Apr 2026 11:24:08 -0700 Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

• Jul 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,586 ($370/night)

]]> https://www.redweek.com/posting/R1445951 Thu, 02 Apr 2026 08:08:33 -0700 Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

• Jul 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,586 ($370/night)

]]> https://www.redweek.com/posting/R1445953 Thu, 02 Apr 2026 08:00:56 -0700 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 Wed, 01 Apr 2026 22:29:21 -0700 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, 01 Apr 2026 17:33:08 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Jul 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,096 ($299/night)

]]> https://www.redweek.com/posting/R1446521 Wed, 01 Apr 2026 16:46:20 -0700 Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Jul 31 – Aug 7, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,748 ($821/night)

]]> https://www.redweek.com/posting/R1455434 Wed, 01 Apr 2026 16:07:43 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Mar 19–26, 2027 (7 nights)
• 2 bed/3 bath, sleeps 8
• $5,693 ($813/night)

]]> https://www.redweek.com/posting/R1453739 Wed, 01 Apr 2026 12:06:39 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 7–21, 2026 (14 nights)
• 2 bed/2 bath, sleeps 8
• $16,033 ($1,145/night)

]]> https://www.redweek.com/posting/R1454273 Wed, 01 Apr 2026 06:19:05 -0700 Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Sep 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1454964 Tue, 31 Mar 2026 18:36:41 -0700 Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

• Nov 22–28, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $4,112 ($685/night)

]]> https://www.redweek.com/posting/R1453231 Tue, 31 Mar 2026 07:08:17 -0700 Verified & Protected

Sands of Kahana Vacation Club

Lahaina, Hawaii

• Aug 15–22, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,878 ($268/night)

]]> https://www.redweek.com/posting/R1442108 Mon, 30 Mar 2026 11:36:08 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Jan 9–16, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1451135 Mon, 30 Mar 2026 11:28:46 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Mar 13–20, 2027 (7 nights)
• 3 bed/3 bath, sleeps 10
• $10,440 ($1,491/night)

]]> https://www.redweek.com/posting/R1450826 Mon, 30 Mar 2026 06:15:03 -0700 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 Sun, 29 Mar 2026 14:41:38 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Feb 14–21, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1453741 Sun, 29 Mar 2026 11:10:17 -0700

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 Sat, 28 Mar 2026 19:56:33 -0700

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 Sat, 28 Mar 2026 19:56:33 -0700

Kahana Beach Resort

Lahaina, Hawaii

• Jan 9–16, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $1,512 ($216/night)

]]> https://www.redweek.com/posting/R1453578 Sat, 28 Mar 2026 19:37:55 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Jan 9–16, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,219 ($1,031/night)

]]> https://www.redweek.com/posting/R1450439 Fri, 27 Mar 2026 13:36:02 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Mar 19–26, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,437 ($1,062/night)

]]> https://www.redweek.com/posting/R1450451 Fri, 27 Mar 2026 13:33:54 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Sep 18–25, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,622 ($517/night)

]]> https://www.redweek.com/posting/R1451386 Thu, 26 Mar 2026 10:27:19 -0700 Voted Top Pick 2026

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

Lahaina, Hawaii

• Jun 28 – Jul 5, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,948 ($564/night)

]]> https://www.redweek.com/posting/R1451367 Wed, 25 Mar 2026 14:01:41 -0700 Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

• Oct 5–11, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $2,641 ($440/night)

]]> https://www.redweek.com/posting/R1437097 Wed, 25 Mar 2026 13:07:01 -0700 Verified & Protected

WorldMark Kihei Resort

Kihei, Hawaii

• Nov 28 – Dec 5, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1445889 Wed, 25 Mar 2026 11:47:32 -0700 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 Tue, 24 Mar 2026 19:38:43 -0700 Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 19–26, 2026 (7 nights)
• 3 bed/3 bath, sleeps 8
• $10,380 ($1,483/night)

]]> https://www.redweek.com/posting/R1449005 Tue, 24 Mar 2026 14:29:09 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1449010 Tue, 24 Mar 2026 14:24:40 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $6,238 ($891/night)

]]> https://www.redweek.com/posting/R1444464 Tue, 24 Mar 2026 09:27:18 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Sep 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,748 ($821/night)

]]> https://www.redweek.com/posting/R1441026 Tue, 24 Mar 2026 08:58:58 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Jun 28 – Jul 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,230 ($747/night)

]]> https://www.redweek.com/posting/R1449748 Tue, 24 Mar 2026 06:10:20 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Nov 27 – Dec 4, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,748 ($821/night)

]]> https://www.redweek.com/posting/R1444347 Fri, 20 Mar 2026 14:55:35 -0700 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Aug 15–22, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1439116 Fri, 20 Mar 2026 10:52:11 -0700 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1439727 Thu, 19 Mar 2026 14:29:32 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Aug 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,294 ($471/night)

]]> https://www.redweek.com/posting/R1443250 Wed, 18 Mar 2026 06:50:52 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Aug 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,420 ($774/night)

]]> https://www.redweek.com/posting/R1447290 Tue, 17 Mar 2026 06:07:15 -0700 Verified & Protected

Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

• Jul 3–10, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,963 ($423/night)

]]> https://www.redweek.com/posting/R1438131 Mon, 16 Mar 2026 12:41:07 -0700 Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Oct 10–17, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1445692 Thu, 12 Mar 2026 17:10:12 -0700 Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

• Jun 25 – Jul 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1438094 Thu, 12 Mar 2026 17:06:54 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Nov 21–28, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,984 ($712/night)

]]> https://www.redweek.com/posting/R1441318 Wed, 11 Mar 2026 07:37:09 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Nov 21–28, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,984 ($712/night)

]]> https://www.redweek.com/posting/R1441319 Wed, 11 Mar 2026 07:33:36 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Nov 21–28, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1441321 Wed, 11 Mar 2026 07:28:28 -0700