https://www.redweek.com/featured/spring-summer-rentals/North+America/United+States/South+Carolina/Hilton+Head+Island?sort=date en Fri, 10 Apr 2026 09:59:35 -0700 3600 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Apr 11–18, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,330 ($190/night)

]]> https://www.redweek.com/posting/R1425242 Wed, 28 Jan 2026 16:15:04 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• Apr 12–19, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,222 ($603/night)

]]> https://www.redweek.com/posting/R1397424 Sun, 07 Dec 2025 07:17:49 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• Apr 13–20, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1397456 Sun, 07 Dec 2025 08:56:04 -0800 Verified & Protected

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina

• Apr 15–20, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $3,730 ($746/night)

]]> https://www.redweek.com/posting/R1338723 Thu, 18 Sep 2025 11:59:30 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• Apr 15–20, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $2,968 ($594/night)

]]> https://www.redweek.com/posting/R1360356 Mon, 10 Nov 2025 16:12:22 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Apr 20 – May 13, 2026 (23 nights)
• 2 bed/2 bath, sleeps 8
• $16,375 ($712/night)

]]> https://www.redweek.com/posting/R1414443 Mon, 19 Jan 2026 06:28:58 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• Apr 22–26, 2026 (4 nights)
• 3 bed/3 bath, sleeps 12
• $3,132 ($783/night)

]]> https://www.redweek.com/posting/R1414714 Fri, 30 Jan 2026 05:46:35 -0800 Verified & Protected

Marriott's Heritage Club

Hilton Head Island, South Carolina

• Apr 24–30, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($458/night)

]]> https://www.redweek.com/posting/R1337892 Tue, 16 Sep 2025 11:36:26 -0700 Verified & Protected

Waterside by Spinnaker

Hilton Head Island, South Carolina

• Apr 25 – May 2, 2026 (7 nights)
• 3 bed/3 bath, sleeps 8
• $777 ($111/night)

]]> https://www.redweek.com/posting/R1437469 Mon, 02 Mar 2026 13:55:09 -0800 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• Apr 25 – May 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1424540 Mon, 02 Feb 2026 06:24:00 -0800 Verified & Protected

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina

• Apr 25–30, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,110 ($222/night)

]]> https://www.redweek.com/posting/R1347709 Wed, 08 Oct 2025 12:22:55 -0700 Verified & Protected

Marriott's Heritage Club

Hilton Head Island, South Carolina

• Apr 25 – May 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,109 ($158/night)

]]> https://www.redweek.com/posting/R1419235 Thu, 22 Jan 2026 06:59:14 -0800 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• Apr 25 – May 2, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1406809 Tue, 30 Dec 2025 12:57:47 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Apr 26 – May 3, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,268 ($467/night)

]]> https://www.redweek.com/posting/R1437171 Tue, 03 Mar 2026 07:14:58 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• Apr 26 – May 3, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $3,617 ($517/night)

]]> https://www.redweek.com/posting/R1428318 Mon, 09 Feb 2026 07:00:58 -0800 Verified & Protected

Royal Dunes Resort

Hilton Head Island, South Carolina

• Apr 26 – May 3, 2026 (7 nights)
• 3 bed/3 bath, sleeps 8
• $1,358 ($194/night)

]]> https://www.redweek.com/posting/R1430912 Fri, 20 Feb 2026 13:44:41 -0800 Verified & Protected

Marriott's Harbour Club at Harbour Town

Hilton Head Island, South Carolina

• Apr 26 – May 2, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $3,513 ($586/night)

]]> https://www.redweek.com/posting/R1316701 Thu, 31 Jul 2025 14:06:25 -0700 Verified & Protected

Players Club of Hilton Head Island

Hilton Head Island, South Carolina

• Apr 29 – May 3, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $722 ($180/night)

]]> https://www.redweek.com/posting/R1423112 Tue, 24 Feb 2026 09:38:26 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

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

]]> https://www.redweek.com/posting/R1430964 Mon, 16 Feb 2026 08:09:30 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• May 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1437374 Mon, 30 Mar 2026 13:49:47 -0700 Verified & Protected

Marriott's Heritage Club

Hilton Head Island, South Carolina

• May 2–6, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $3,404 ($851/night)

]]> https://www.redweek.com/posting/R1431132 Tue, 10 Feb 2026 06:28:36 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• May 2–9, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $3,077 ($440/night)

]]> https://www.redweek.com/posting/R1402676 Tue, 16 Dec 2025 07:42:54 -0800 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• May 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,878 ($268/night)

]]> https://www.redweek.com/posting/R1456511 Tue, 07 Apr 2026 06:18:54 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 3–10, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,123 ($303/night)

]]> https://www.redweek.com/posting/R1444705 Fri, 13 Mar 2026 11:37:25 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 3–8, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $2,859 ($572/night)

]]> https://www.redweek.com/posting/R1420951 Tue, 20 Jan 2026 07:41:07 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 3–8, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $2,096 ($419/night)

]]> https://www.redweek.com/posting/R1439027 Fri, 03 Apr 2026 11:42:21 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• May 3–10, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,451 ($493/night)

]]> https://www.redweek.com/posting/R1437174 Tue, 03 Mar 2026 07:19:22 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• May 4–7, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $1,082 ($361/night)

]]> https://www.redweek.com/posting/R1440950 Mon, 23 Mar 2026 06:41:59 -0700

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina

• May 5–10, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,110 ($222/night)

]]> https://www.redweek.com/posting/R1458409 Wed, 08 Apr 2026 11:46:15 -0700 Verified & Protected

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina

• May 7–11, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $999 ($250/night)

]]> https://www.redweek.com/posting/R1451171 Fri, 27 Mar 2026 14:01:29 -0700 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1451239 Mon, 30 Mar 2026 11:51:29 -0700 Verified & Protected

Marriott's Heritage Club

Hilton Head Island, South Carolina

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1345550 Thu, 02 Oct 2025 04:22:14 -0700 Verified & Protected

Marriott's Heritage Club

Hilton Head Island, South Carolina

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1377098 Thu, 20 Nov 2025 06:51:45 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,112 ($588/night)

]]> https://www.redweek.com/posting/R1450902 Fri, 27 Mar 2026 14:32:35 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• May 8–15, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1457220 Wed, 08 Apr 2026 07:22:01 -0700 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1445989 Mon, 06 Apr 2026 06:26:49 -0700 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 3 bed/3 bath, sleeps 12
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1410816 Fri, 02 Jan 2026 11:35:36 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1393370 Fri, 28 Nov 2025 12:27:01 -0800 Verified & Protected

Ocean Oak Resort by Hilton Grand Vacations

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,731 ($533/night)

]]> https://www.redweek.com/posting/R1350783 Fri, 17 Oct 2025 06:05:46 -0700 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,696 ($385/night)

]]> https://www.redweek.com/posting/R1425838 Tue, 10 Feb 2026 07:07:00 -0800 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1360352 Mon, 10 Nov 2025 16:04:22 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,749 ($393/night)

]]> https://www.redweek.com/posting/R1423952 Tue, 27 Jan 2026 07:17:52 -0800 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1443587 Fri, 13 Mar 2026 13:38:25 -0700 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,742 ($249/night)

]]> https://www.redweek.com/posting/R1326894 Fri, 22 Aug 2025 10:46:06 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,832 ($405/night)

]]> https://www.redweek.com/posting/R1413715 Wed, 07 Jan 2026 09:31:28 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1457176 Wed, 08 Apr 2026 06:33:01 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,291 ($470/night)

]]> https://www.redweek.com/posting/R1315350 Mon, 28 Jul 2025 08:31:45 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 9–16, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,987 ($284/night)

]]> https://www.redweek.com/posting/R1440567 Wed, 11 Mar 2026 06:14:43 -0700