Rentals with Flexible Cancellation Policies
These flexible rentals are fully refundable up to 65 days before check-in. Most of our units are owned by individuals, who need plenty of advance notice as they have just a single week of use per year with limited last-minute options.
Verified & Protected
Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jul 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
Verified & Protected
Bluewater Resort & Marina
Hilton Head Island, South Carolina- Apr 12–19, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,290 ($470/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Sep 13–20, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
Verified & Protected
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Sep 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,220 ($244/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Jul 31 – Aug 3, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($880/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Nov 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($332/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,145 ($592/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Aug 30 – Sep 4, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($441/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Apr 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Jul 18–25, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Oct 31 – Nov 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jul 31 – Aug 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Aug 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Aug 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Jul 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Verified & Protected
Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,764 ($538/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Mar 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Mar 22–27, 2026 (5 nights)
- 3 bed/3 bath, sleeps 12
- $2,313 ($463/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jul 26 – Aug 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Jul 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $5,404 ($772/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,341 ($468/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Apr 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 23–29, 2026 (6 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($640/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Apr 15–20, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($577/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Mar 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,368 ($338/night)
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)
Verified & Protected
Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Apr 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Apr 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Apr 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Sep 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($550/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Mar 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($377/night)