https://www.redweek.com/featured/flexible-rentals/North+America/United+States/Hawaii en Mon, 25 May 2026 06:40:46 -0700 3600 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 13–20, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1475925 Sat, 23 May 2026 20:37:47 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Mar 6–13, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1475923 Sat, 23 May 2026 20:37:47 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Jun 5–10, 2027 (5 nights)
• 2 bed/2 bath, sleeps 8
• $4,494 ($899/night)

]]> https://www.redweek.com/posting/R1473114 Fri, 22 May 2026 11:51:56 -0700 Verified & Protected

Club Wyndham Mauna Loa Village

Kailua-Kona, Hawaii

• Oct 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,418 ($631/night)

]]> https://www.redweek.com/posting/R1475201 Fri, 22 May 2026 10:49:22 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Nov 22–29, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $10,699 ($1,528/night)

]]> https://www.redweek.com/posting/R1474974 Thu, 21 May 2026 12:42:32 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jan 10–14, 2027 (4 nights)
• 1 bed/1 bath, sleeps 4
• $2,074 ($519/night)

]]> https://www.redweek.com/posting/R1474861 Thu, 21 May 2026 11:31:52 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Aug 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1470024 Thu, 21 May 2026 09:44:14 -0700 Verified & Protected

Royal Kuhio

Honolulu, Hawaii

• Aug 16–23, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,987 ($284/night)

]]> https://www.redweek.com/posting/R1473372 Wed, 20 May 2026 15:26:54 -0700 Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

• Aug 27 – Sep 3, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $999 ($143/night)

]]> https://www.redweek.com/posting/R1473233 Tue, 19 May 2026 09:33:45 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Mar 27 – Apr 3, 2027 (7 nights)
• 1 bed/2 bath, sleeps 4
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1473001 Tue, 19 May 2026 09:13:15 -0700 Verified & Protected

Sands of Kahana Vacation Club

Lahaina, Hawaii

• Nov 22–29, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $2,908 ($415/night)

]]> https://www.redweek.com/posting/R1471484 Mon, 18 May 2026 11:48:34 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Aug 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1473055 Mon, 18 May 2026 08:24:34 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Sep 30 – Oct 7, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1472937 Fri, 15 May 2026 13:31:30 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Feb 20–27, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1472985 Fri, 15 May 2026 13:01:05 -0700 Verified & Protected 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 Fri, 15 May 2026 12:08:02 -0700 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Sep 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1472273 Wed, 13 May 2026 13:17:11 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Nov 24–25, 2026 (1 night)
• 1 bed/1 bath, sleeps 4
• $555 ($555/night)

]]> https://www.redweek.com/posting/R1472026 Wed, 13 May 2026 09:33:12 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1471957 Wed, 13 May 2026 08:23:14 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Nov 27 – Dec 4, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1471956 Wed, 13 May 2026 08:19:33 -0700 Verified & Protected

Pono Kai

Kapaa, Hawaii

• Nov 20–27, 2026 (7 nights)
• 1 bed/1 bath, sleeps 6
• $1,769 ($253/night)

]]> https://www.redweek.com/posting/R1471952 Wed, 13 May 2026 08:15:41 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Jan 29 – Feb 5, 2027 (7 nights)
• Studio/1 bath, sleeps 4
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1457165 Tue, 12 May 2026 14:07:58 -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
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1457175 Tue, 12 May 2026 13:41:39 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Jun 6–13, 2027 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1470890 Tue, 12 May 2026 08:19:52 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Dec 18–25, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,047 ($292/night)

]]> https://www.redweek.com/posting/R1471068 Tue, 12 May 2026 07:43:53 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,276 ($325/night)

]]> https://www.redweek.com/posting/R1471067 Tue, 12 May 2026 07:43:36 -0700 Verified & Protected

WorldMark Kona Resort

Kailua-Kona, Hawaii

• Oct 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,022 ($432/night)

]]> https://www.redweek.com/posting/R1470231 Fri, 08 May 2026 13:33:29 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Oct 25 – Nov 1, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,817 ($688/night)

]]> https://www.redweek.com/posting/R1468180 Fri, 08 May 2026 10:19:59 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Nov 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,817 ($688/night)

]]> https://www.redweek.com/posting/R1468186 Fri, 08 May 2026 10:19:13 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Nov 25 – Dec 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,655 ($1,094/night)

]]> https://www.redweek.com/posting/R1470239 Thu, 07 May 2026 14:42:41 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,587 ($941/night)

]]> https://www.redweek.com/posting/R1468974 Thu, 07 May 2026 11:22:31 -0700 Verified & Protected

Sands of Kahana Vacation Club

Lahaina, Hawaii

• Mar 14–21, 2027 (7 nights)
• 3 bed/2 bath, sleeps 8
• $4,494 ($642/night)

]]> https://www.redweek.com/posting/R1467114 Thu, 07 May 2026 11:15:21 -0700 Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

• Nov 3–12, 2026 (9 nights)
• 1 bed/1 bath, sleeps 4
• $4,930 ($548/night)

]]> https://www.redweek.com/posting/R1469318 Thu, 07 May 2026 07:50:47 -0700 Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/2 bath, sleeps 6
• $1,649 ($236/night)

]]> https://www.redweek.com/posting/R1439465 Thu, 07 May 2026 07:33:18 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Sep 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,949 ($564/night)

]]> https://www.redweek.com/posting/R1442267 Wed, 06 May 2026 18:25:44 -0700 Verified & Protected

Sheraton Kauai Resort Villas

Koloa, Hawaii

• Jan 16–23, 2027 (7 nights)
• Studio/1 bath, sleeps 2
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1467854 Wed, 06 May 2026 08:17:21 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Oct 24–31, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,475 ($782/night)

]]> https://www.redweek.com/posting/R1468078 Wed, 06 May 2026 08:05:25 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Nov 22–29, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $6,510 ($930/night)

]]> https://www.redweek.com/posting/R1469294 Tue, 05 May 2026 15:06:23 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Aug 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $6,565 ($938/night)

]]> https://www.redweek.com/posting/R1467964 Tue, 05 May 2026 14:58:22 -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
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1468608 Tue, 05 May 2026 14:46:17 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Feb 20–27, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,565 ($938/night)

]]> https://www.redweek.com/posting/R1468760 Mon, 04 May 2026 13:27:35 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Feb 21–28, 2027 (7 nights)
• 3 bed/3 bath, sleeps 10
• $11,470 ($1,639/night)

]]> https://www.redweek.com/posting/R1466331 Mon, 04 May 2026 13:21:59 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Feb 6–13, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,510 ($930/night)

]]> https://www.redweek.com/posting/R1468515 Mon, 04 May 2026 09:07:30 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

• Aug 22–29, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,649 ($521/night)

]]> https://www.redweek.com/posting/R1467475 Fri, 01 May 2026 14:35:49 -0700 Verified & Protected

Maui Schooner

Kihei, Hawaii

• Sep 25 – Oct 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1466944 Fri, 01 May 2026 13:31:12 -0700 Verified & Protected

Club Wyndham Ka 'Eo Kai

Princeville, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,839 ($548/night)

]]> https://www.redweek.com/posting/R1465375 Thu, 30 Apr 2026 17:36:25 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Nov 28 – Dec 5, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,110 ($1,016/night)

]]> https://www.redweek.com/posting/R1466976 Thu, 30 Apr 2026 06:57:44 -0700 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Nov 24–30, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $2,804 ($467/night)

]]> https://www.redweek.com/posting/R1465081 Wed, 29 Apr 2026 13:36:14 -0700 Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

• Nov 7–14, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,726 ($532/night)

]]> https://www.redweek.com/posting/R1464706 Wed, 29 Apr 2026 08:10:58 -0700