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.
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Voted Top Pick 2025
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)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 23–29, 2026 (6 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($640/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,879 ($411/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,042 ($292/night)
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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)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,818 ($545/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,786 ($541/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
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Voted Top Pick 2025
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)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,262 ($466/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,257 ($465/night)
Verified & Protected
Voted Top Pick 2025
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 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,676 ($525/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 23–29, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($222/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
Verified & Protected
Voted Top Pick 2025
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)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,617 ($517/night)
Verified & Protected
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,009 ($287/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,659 ($332/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,329 ($266/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,324 ($265/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 24–28, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($551/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 24–29, 2026 (5 nights)
- 3 bed/3 bath, sleeps 12
- $3,295 ($659/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 24–29, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,549 ($310/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 25 – Jun 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 29 – Jun 6, 2026 (8 nights)
- 3 bed/3 bath, sleeps 12
- $5,693 ($712/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 29 – Jun 5, 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- May 29 – Jun 5, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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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- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)