https://www.redweek.com/featured/winter-rentals/North+America/United+States/Hawaii/Hawaii+(Big+Island)?sort=date en Sun, 05 Apr 2026 13:11:48 -0700 3600 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 5–12, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,183 ($312/night)

]]> https://www.redweek.com/posting/R1432253 Mon, 09 Mar 2026 11:21:09 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 5–10, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,859 ($572/night)

]]> https://www.redweek.com/posting/R1426664 Tue, 03 Feb 2026 07:00:09 -0800 Verified & Protected

Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

• Dec 16–27, 2026 (11 nights)
• 2 bed/2 bath, sleeps 6
• $5,366 ($488/night)

]]> https://www.redweek.com/posting/R1427890 Fri, 03 Apr 2026 15:17:54 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 18–24, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $3,622 ($604/night)

]]> https://www.redweek.com/posting/R1421928 Thu, 22 Jan 2026 15:38:08 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 18–23, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $4,325 ($865/night)

]]> https://www.redweek.com/posting/R1428184 Tue, 03 Feb 2026 18:18:42 -0800 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1367855 Fri, 14 Nov 2025 23:47:43 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $5,540 ($791/night)

]]> https://www.redweek.com/posting/R1415182 Mon, 19 Jan 2026 07:03:36 -0800 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,925 ($704/night)

]]> https://www.redweek.com/posting/R1417879 Fri, 23 Jan 2026 14:39:30 -0800 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $10,925 ($1,561/night)

]]> https://www.redweek.com/posting/R1436865 Mon, 16 Mar 2026 17:39:38 -0700 Verified & Protected

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1427376 Tue, 24 Feb 2026 12:52:44 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $10,380 ($1,483/night)

]]> https://www.redweek.com/posting/R1445689 Mon, 16 Mar 2026 07:21:01 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $5,693 ($813/night)

]]> https://www.redweek.com/posting/R1390583 Mon, 01 Dec 2025 06:10:18 -0800 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,265 ($609/night)

]]> https://www.redweek.com/posting/R1434010 Fri, 06 Mar 2026 18:48:11 -0800 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 19–26, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,832 ($690/night)

]]> https://www.redweek.com/posting/R1435653 Thu, 12 Mar 2026 11:32:19 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 20–27, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $5,257 ($751/night)

]]> https://www.redweek.com/posting/R1418607 Mon, 19 Jan 2026 06:09:10 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 20–27, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $9,835 ($1,405/night)

]]> https://www.redweek.com/posting/R1437516 Wed, 04 Mar 2026 17:43:23 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 20–27, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,712 ($673/night)

]]> https://www.redweek.com/posting/R1446935 Tue, 17 Mar 2026 05:37:51 -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

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,380 ($626/night)

]]> https://www.redweek.com/posting/R1437494 Thu, 12 Mar 2026 14:11:29 -0700 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,766 ($681/night)

]]> https://www.redweek.com/posting/R1424913 Tue, 10 Feb 2026 07:46:23 -0800

Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,932 ($276/night)

]]> https://www.redweek.com/posting/R1455749 Thu, 02 Apr 2026 12:50:53 -0700 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $5,470 ($781/night)

]]> https://www.redweek.com/posting/R1417875 Thu, 29 Jan 2026 11:41:21 -0800 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
• $4,636 ($662/night)

]]> https://www.redweek.com/posting/R1431922 Thu, 05 Mar 2026 11:53:21 -0800 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,968 ($424/night)

]]> https://www.redweek.com/posting/R1413516 Wed, 07 Jan 2026 09:48:11 -0800 Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,492 ($642/night)

]]> https://www.redweek.com/posting/R1407532 Wed, 14 Jan 2026 07:12:49 -0800 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Dec 26, 2026 – Jan 2, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1432651 Thu, 19 Mar 2026 14:24:14 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 27, 2026 – Jan 2, 2027 (6 nights)
• 1 bed/1 bath, sleeps 4
• $3,948 ($658/night)

]]> https://www.redweek.com/posting/R1426934 Mon, 09 Feb 2026 05:53:05 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Dec 29, 2026 – Jan 5, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $6,946 ($992/night)

]]> https://www.redweek.com/posting/R1409683 Tue, 30 Dec 2025 17:46:26 -0800 Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

• Jan 2–9, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1437991 Thu, 12 Mar 2026 18:12:47 -0700 Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

• Jan 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,112 ($588/night)

]]> https://www.redweek.com/posting/R1411232 Wed, 14 Jan 2026 13:32:18 -0800 Verified & Protected

Kona Coast Resort

Kailua-Kona, Hawaii

• Jan 8–22, 2027 (14 nights)
• 1 bed/2 bath, sleeps 4
• $4,058 ($290/night)

]]> https://www.redweek.com/posting/R1426052 Wed, 25 Feb 2026 14:42:57 -0800 Verified & Protected

WorldMark Kona Resort

Kailua-Kona, Hawaii

• Jan 14–24, 2027 (10 nights)
• 2 bed/2 bath, sleeps 6
• $2,750 ($275/night)

]]> https://www.redweek.com/posting/R1444787 Mon, 16 Mar 2026 14:42:21 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Jan 17–24, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,166 ($595/night)

]]> https://www.redweek.com/posting/R1434129 Wed, 18 Feb 2026 07:02:19 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Jan 23–30, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,020 ($860/night)

]]> https://www.redweek.com/posting/R1427618 Thu, 05 Feb 2026 06:11:59 -0800 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Jan 31 – Feb 7, 2027 (7 nights)
• 1 bed/1 bath, sleeps 4
• $4,984 ($712/night)

]]> https://www.redweek.com/posting/R1444457 Mon, 16 Mar 2026 11:13:58 -0700 Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

• Feb 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,380 ($626/night)

]]> https://www.redweek.com/posting/R1409798 Fri, 02 Jan 2026 06:18:29 -0800