https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii en Tue, 04 Aug 2026 00:47:09 -0700 3600 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $5,911 ($844/night)

]]> https://www.redweek.com/posting/R1396693 Thu, 04 Dec 2025 19:07:57 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1446056 Tue, 24 Mar 2026 09:06:52 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,916 ($559/night)

]]> https://www.redweek.com/posting/R1504984 Sun, 02 Aug 2026 23:06:14 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $2,804 ($467/night)

]]> https://www.redweek.com/posting/R1437659 Wed, 25 Feb 2026 10:15:08 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $9,936 ($1,419/night)

]]> https://www.redweek.com/posting/R1411325 Wed, 07 Jan 2026 07:53:14 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,595 ($656/night)

]]> https://www.redweek.com/posting/R1503381 Mon, 27 Jul 2026 13:57:15 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 1–6, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,423 ($485/night)

]]> https://www.redweek.com/posting/R1471899 Tue, 19 May 2026 09:00:22 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,669 ($953/night)

]]> https://www.redweek.com/posting/R1454724 Tue, 31 Mar 2026 10:57:11 -0700 Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1493960 Mon, 06 Jul 2026 09:50:31 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,671 ($810/night)

]]> https://www.redweek.com/posting/R1434890 Thu, 19 Feb 2026 12:27:28 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• 3 bed/3 bath, sleeps 10
• $7,862 ($1,310/night)

]]> https://www.redweek.com/posting/R1412939 Tue, 06 Jan 2026 08:35:14 -0800 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,707 ($672/night)

]]> https://www.redweek.com/posting/R1486313 Fri, 19 Jun 2026 09:53:44 -0700 Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,260 ($323/night)

]]> https://www.redweek.com/posting/R1407461 Fri, 26 Dec 2025 12:44:20 -0800 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

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

• Dec 2–7, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,987 ($397/night)

]]> https://www.redweek.com/posting/R1448659 Wed, 06 May 2026 15:07:58 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,568 ($510/night)

]]> https://www.redweek.com/posting/R1478058 Tue, 02 Jun 2026 06:55:13 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 3–10, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,451 ($493/night)

]]> https://www.redweek.com/posting/R1456697 Tue, 07 Apr 2026 06:42:40 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 3–7, 2026 (4 nights)
• Studio/1 bath, sleeps 4
• $2,188 ($547/night)

]]> https://www.redweek.com/posting/R1483217 Fri, 12 Jun 2026 17:08:39 -0700 Verified & Protected

Kahana Falls

Lahaina, Hawaii

• Dec 3–10, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $2,096 ($299/night)

]]> https://www.redweek.com/posting/R1440983 Wed, 01 Apr 2026 14:58:25 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 4–7, 2026 (3 nights)
• Studio/1 bath, sleeps 4
• $1,647 ($549/night)

]]> https://www.redweek.com/posting/R1483220 Fri, 12 Jun 2026 17:08:39 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($767/night)

]]> https://www.redweek.com/posting/R1493360 Tue, 07 Jul 2026 10:54:48 -0700 Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1506105 Sat, 01 Aug 2026 09:27:06 -0700 Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

• Dec 4–9, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $2,510 ($502/night)

]]> https://www.redweek.com/posting/R1503942 Mon, 27 Jul 2026 17:46:59 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,489 ($641/night)

]]> https://www.redweek.com/posting/R1505903 Mon, 03 Aug 2026 23:06:10 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $6,121 ($874/night)

]]> https://www.redweek.com/posting/R1465535 Tue, 28 Apr 2026 08:22:26 -0700 Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,385 ($626/night)

]]> https://www.redweek.com/posting/R1459563 Mon, 13 Apr 2026 11:17:52 -0700 Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,489 ($641/night)

]]> https://www.redweek.com/posting/R1505894 Mon, 03 Aug 2026 23:05:28 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 4–7, 2026 (3 nights)
• Studio/1 bath, sleeps 4
• $1,620 ($540/night)

]]> https://www.redweek.com/posting/R1483219 Fri, 12 Jun 2026 17:08:39 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,886 ($412/night)

]]> https://www.redweek.com/posting/R1417211 Mon, 19 Jan 2026 06:31:51 -0800 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–9, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $1,932 ($386/night)

]]> https://www.redweek.com/posting/R1504396 Wed, 29 Jul 2026 20:39:59 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $3,649 ($521/night)

]]> https://www.redweek.com/posting/R1504293 Tue, 28 Jul 2026 12:50:36 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,954 ($565/night)

]]> https://www.redweek.com/posting/R1494875 Wed, 08 Jul 2026 11:01:45 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 4–11, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,412 ($630/night)

]]> https://www.redweek.com/posting/R1504164 Tue, 28 Jul 2026 12:30:16 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,112 ($588/night)

]]> https://www.redweek.com/posting/R1490892 Wed, 01 Jul 2026 13:29:15 -0700 Verified & Protected

Maui Beach Vacation Club

Kihei, Hawaii

• Dec 4–11, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $1,650 ($236/night)

]]> https://www.redweek.com/posting/R1502247 Fri, 24 Jul 2026 13:04:05 -0700 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

• Dec 4–11, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $3,153 ($450/night)

]]> https://www.redweek.com/posting/R1502557 Fri, 24 Jul 2026 13:39:29 -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 Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,649 ($521/night)

]]> https://www.redweek.com/posting/R1455028 Tue, 14 Apr 2026 14:11:51 -0700 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 5–12, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $4,930 ($704/night)

]]> https://www.redweek.com/posting/R1469454 Mon, 01 Jun 2026 15:07:51 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,306 ($472/night)

]]> https://www.redweek.com/posting/R1476397 Mon, 25 May 2026 18:38:16 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka'anapali Beach

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $11,466 ($1,638/night)

]]> https://www.redweek.com/posting/R1480757 Mon, 08 Jun 2026 10:53:18 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,475 ($782/night)

]]> https://www.redweek.com/posting/R1477653 Fri, 29 May 2026 06:07:17 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,911 ($844/night)

]]> https://www.redweek.com/posting/R1470827 Tue, 09 Jun 2026 12:46:15 -0700 Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka'anapali Beach

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $9,143 ($1,306/night)

]]> https://www.redweek.com/posting/R1495958 Fri, 10 Jul 2026 12:13:37 -0700 Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,565 ($652/night)

]]> https://www.redweek.com/posting/R1495705 Fri, 10 Jul 2026 08:22:56 -0700 Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,039 ($720/night)

]]> https://www.redweek.com/posting/R1412136 Sun, 04 Jan 2026 15:49:39 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 5–12, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,206 ($744/night)

]]> https://www.redweek.com/posting/R1498359 Tue, 21 Jul 2026 11:03:22 -0700 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/2 bath, sleeps 4
• $4,330 ($619/night)

]]> https://www.redweek.com/posting/R1490837 Tue, 30 Jun 2026 15:55:10 -0700