https://www.redweek.com/featured/flexible-rentals/North+America/United+States/Hawaii en Fri, 05 Jun 2026 19:15:01 -0700 3600 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Sep 26 – Oct 3, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1478447 Fri, 05 Jun 2026 13:31:50 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Nov 21–28, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $10,803 ($1,543/night)

]]> https://www.redweek.com/posting/R1480403 Fri, 05 Jun 2026 08:26:05 -0700 Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• May 29 – Jun 5, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,276 ($611/night)

]]> https://www.redweek.com/posting/R1480291 Thu, 04 Jun 2026 16:46:24 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,602 ($657/night)

]]> https://www.redweek.com/posting/R1480118 Thu, 04 Jun 2026 11:40:56 -0700 Verified & Protected

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,769 ($824/night)

]]> https://www.redweek.com/posting/R1478964 Wed, 03 Jun 2026 10:46:18 -0700 Verified & Protected

The Point at Poipu

Koloa, Hawaii

• Feb 14–21, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,214 ($602/night)

]]> https://www.redweek.com/posting/R1479460 Wed, 03 Jun 2026 08:50:50 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Jan 30 – Feb 7, 2027 (8 nights)
• 1 bed/1 bath, sleeps 4
• $4,603 ($575/night)

]]> https://www.redweek.com/posting/R1478277 Tue, 02 Jun 2026 09:54:22 -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
• $7,546 ($1,078/night)

]]> https://www.redweek.com/posting/R1478275 Tue, 02 Jun 2026 09:32:39 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 20–27, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $8,036 ($1,148/night)

]]> https://www.redweek.com/posting/R1478735 Mon, 01 Jun 2026 14:02:40 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Oct 30 – Nov 6, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,470 ($781/night)

]]> https://www.redweek.com/posting/R1477661 Fri, 29 May 2026 08:15:06 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Nov 21–28, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,701 ($957/night)

]]> https://www.redweek.com/posting/R1477637 Fri, 29 May 2026 07:58:43 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 13–20, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1477271 Thu, 28 May 2026 09:25:13 -0700 Verified & Protected

The Point at Poipu

Koloa, Hawaii

• Dec 14–20, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($549/night)

]]> https://www.redweek.com/posting/R1476752 Wed, 27 May 2026 14:46:12 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Jan 3–10, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,058 ($580/night)

]]> https://www.redweek.com/posting/R1476981 Wed, 27 May 2026 13:13:01 -0700 Verified & Protected

Alii Kai Resort

Princeville, Hawaii

• Sep 26 – Oct 3, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,194 ($313/night)

]]> https://www.redweek.com/posting/R1475242 Wed, 27 May 2026 07:20:36 -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
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1475925 Mon, 25 May 2026 14:25:03 -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
• $3,840 ($549/night)

]]> https://www.redweek.com/posting/R1475923 Mon, 25 May 2026 14:24:50 -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

Club Wyndham Bali Hai Villas

Princeville, Hawaii

• Aug 27 – Sep 3, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $944 ($135/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

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
• $4,222 ($603/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
• $4,222 ($603/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 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

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