Spring Summer Rentals
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)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,294 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,268 ($467/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($332/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 14–17, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $3,294 ($1,098/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,191 ($456/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,914 ($416/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,076 ($439/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,260 ($323/night)
Verified & Protected
Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 16–22, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,968 ($495/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Royal Dunes Resort
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,987 ($284/night)
Verified & Protected
Marriott's Heritage Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,467 ($352/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,058 ($580/night)
Verified & Protected
Island Links Resort
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $2,091 ($299/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Bluewater Resort & Marina
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($221/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($412/night)
Verified & Protected
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($531/night)
Verified & Protected
Marriott's Heritage Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 22–27, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($310/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,268 ($467/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,829 ($547/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($432/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–28, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($458/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
Verified & Protected
Marriott's Heritage Club
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/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
- $3,159 ($451/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)