https://www.redweek.com/featured/flexible-rentals/North+America/United+States/South+Carolina/Hilton+Head+Island en Mon, 05 Oct 2026 12:57:38 -0700 3600 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Aug 13–18, 2027 (5 nights)
• 2 bed/2 bath, sleeps 8
• $6,560 ($1,199/night)

]]> https://www.redweek.com/posting/R1533432 Sat, 03 Oct 2026 18:24:48 -0700 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• Apr 13–20, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,840 ($500/night)

]]> https://www.redweek.com/posting/R1532434 Thu, 01 Oct 2026 10:42:30 -0700 Verified & Protected

Waterside by Spinnaker

Hilton Head Island, South Carolina

• Jul 31 – Aug 7, 2027 (7 nights)
• 3 bed/3 bath, sleeps 8
• $2,505 ($325/night)

]]> https://www.redweek.com/posting/R1531285 Mon, 28 Sep 2026 19:48:52 -0700 Verified & Protected

Waterside by Spinnaker

Hilton Head Island, South Carolina

• Aug 14–21, 2027 (7 nights)
• 3 bed/3 bath, sleeps 8
• $2,505 ($325/night)

]]> https://www.redweek.com/posting/R1531287 Mon, 28 Sep 2026 19:48:52 -0700 Verified & Protected

Waterside by Spinnaker

Hilton Head Island, South Carolina

• Aug 7–14, 2027 (7 nights)
• 3 bed/3 bath, sleeps 8
• $2,505 ($325/night)

]]> https://www.redweek.com/posting/R1531286 Mon, 28 Sep 2026 19:48:52 -0700 Verified & Protected

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina

• Jul 10–17, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,069 ($530/night)

]]> https://www.redweek.com/posting/R1532328 Thu, 01 Oct 2026 07:41:13 -0700 Verified & Protected

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina

• Jul 21–25, 2027 (4 nights)
• 2 bed/2 bath, sleeps 6
• $1,528 ($345/night)

]]> https://www.redweek.com/posting/R1530254 Sat, 26 Sep 2026 05:46:53 -0700 Verified & Protected

Players Club of Hilton Head Island

Hilton Head Island, South Carolina

• Sep 5–12, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1529462 Wed, 23 Sep 2026 17:51:50 -0700 Verified & Protected

Players Club of Hilton Head Island

Hilton Head Island, South Carolina

• Aug 1–8, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,165 ($150/night)

]]> https://www.redweek.com/posting/R1529460 Wed, 23 Sep 2026 17:43:42 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Apr 2–9, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,993 ($520/night)

]]> https://www.redweek.com/posting/R1528905 Tue, 22 Sep 2026 14:05:19 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Aug 15–21, 2027 (6 nights)
• 2 bed/2 bath, sleeps 8
• $3,942 ($599/night)

]]> https://www.redweek.com/posting/R1525415 Mon, 14 Sep 2026 17:35:17 -0700 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• Jun 12–19, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($450/night)

]]> https://www.redweek.com/posting/R1524712 Sun, 13 Sep 2026 04:55:22 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Aug 1–6, 2027 (5 nights)
• 2 bed/2 bath, sleeps 8
• $3,295 ($600/night)

]]> https://www.redweek.com/posting/R1514686 Thu, 27 Aug 2026 12:44:36 -0700 Verified & Protected

Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina

• Sep 4–11, 2027 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,458 ($450/night)

]]> https://www.redweek.com/posting/R1507958 Tue, 18 Aug 2026 13:19:51 -0700 Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina

• Jul 23–30, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,061 ($529/night)

]]> https://www.redweek.com/posting/R1509614 Tue, 11 Aug 2026 07:53:30 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• Jul 25 – Aug 1, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,984 ($650/night)

]]> https://www.redweek.com/posting/R1509623 Tue, 11 Aug 2026 07:37:48 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• May 23–28, 2027 (5 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($500/night)

]]> https://www.redweek.com/posting/R1507938 Wed, 05 Aug 2026 10:54:16 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Mar 14–21, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,268 ($425/night)

]]> https://www.redweek.com/posting/R1503690 Tue, 28 Jul 2026 07:51:09 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Mar 21–28, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,268 ($425/night)

]]> https://www.redweek.com/posting/R1503703 Tue, 28 Jul 2026 07:43:59 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

• Jul 23–30, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,892 ($900/night)

]]> https://www.redweek.com/posting/R1502885 Tue, 28 Jul 2026 06:51:24 -0700 Verified & Protected

Marriott's Heritage Club

Hilton Head Island, South Carolina

• Jul 1–7, 2027 (6 nights)
• 2 bed/2 bath, sleeps 8
• $2,759 ($418/night)

]]> https://www.redweek.com/posting/R1501528 Fri, 24 Jul 2026 10:02:17 -0700 Verified & Protected

Marriott's Harbour Club at Harbour Town

Hilton Head Island, South Carolina

• Apr 4–11, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,458 ($450/night)

]]> https://www.redweek.com/posting/R1501575 Fri, 24 Jul 2026 08:43:24 -0700 Verified & Protected

Marriott's Harbour Club at Harbour Town

Hilton Head Island, South Carolina

• Apr 11–18, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,840 ($500/night)

]]> https://www.redweek.com/posting/R1501586 Fri, 24 Jul 2026 08:41:54 -0700 Verified & Protected

Coral Reef Resort

Hilton Head Island, South Carolina

• Jul 3–10, 2027 (7 nights)
• 3 bed/3.5 bath, sleeps 8
• $1,396 ($180/night)

]]> https://www.redweek.com/posting/R1495096 Thu, 09 Jul 2026 07:03:19 -0700 Verified & Protected

Marriott's Harbour Club at Harbour Town

Hilton Head Island, South Carolina

• Jun 27 – Jul 4, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($357/night)

]]> https://www.redweek.com/posting/R1493667 Tue, 07 Jul 2026 08:06:03 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Apr 11–18, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,475 ($714/night)

]]> https://www.redweek.com/posting/R1482043 Thu, 11 Jun 2026 10:52:21 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Grande Ocean

Hilton Head Island, South Carolina

• Apr 10–17, 2027 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,366 ($700/night)

]]> https://www.redweek.com/posting/R1462196 Tue, 21 Apr 2026 12:15:35 -0700