Spring Summer Rentals
Did you know that 75% of travelers book their spring and summer travel at least 3 months in advance? Unlock exceptional resort deals for your upcoming seasonal getaways before they sell out. Whether you're planning a family vacation, a couple's trip, or a solo adventure, these deals offer the best opportunities to elevate your next travel experience.
Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/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
- $2,532 ($362/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
- $3,730 ($533/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
- $3,077 ($440/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
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Verified & Protected
Marriott's Heritage Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,505 ($358/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,497 ($357/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,489 ($356/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
- $3,949 ($564/night)
Verified & Protected
Marriott's Heritage Club
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,439 ($288/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
- $4,004 ($572/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
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($354/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 3 bed/3 bath, sleeps 12
- $2,527 ($505/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
- $3,949 ($564/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
- $4,494 ($642/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,965 ($393/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 18–22, 2026 (4 nights)
- 3 bed/3 bath, sleeps 12
- $1,987 ($497/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
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 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/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
- $3,458 ($494/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
- $4,385 ($626/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,894 ($556/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
- $3,802 ($543/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,731 ($533/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
- $4,167 ($595/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
- $3,949 ($564/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–28, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($549/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
- $3,295 ($471/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 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
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,622 ($517/night)
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
- $3,922 ($560/night)
Verified & Protected
Sea Crest Surf and Racquet Club
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 1 bed/1.5 bath, sleeps 6
- $1,110 ($159/night)
Verified & Protected
Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($253/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 Grande Ocean
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/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
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/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
- $3,295 ($471/night)