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 Heritage Club
Hilton Head Island, South Carolina- May 4–9, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,764 ($319/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 4–11, 2025 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,298 ($560/night)
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Vacation Time of Hilton Head Island - Ocean Dunes
Hilton Head Island, South Carolina- May 4–11, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($229/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 4–9, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,578 ($285/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 6–13, 2025 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,412 ($575/night)
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 8–13, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,750 ($350/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 9–16, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($375/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($471/night)
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Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($357/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($425/night)
Verified & Protected
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($471/night)
Verified & Protected
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($350/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,225 ($461/night)
Port O'Call
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,490 ($213/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($425/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,786 ($493/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($214/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($571/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($429/night)
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Vacation Time of Hilton Head Island - Ocean Dunes
Hilton Head Island, South Carolina- May 11–18, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($229/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 11–16, 2025 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,764 ($319/night)
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Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 11–16, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($400/night)
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Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 11–16, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,017 ($549/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,894 ($507/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($250/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 16–21, 2025 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,804 ($510/night)
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,495 ($356/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($457/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($425/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($429/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,039 ($395/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,022 ($393/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($500/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,225 ($461/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,600 ($514/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($500/night)
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The Village at Palmetto Dunes
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($286/night)
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 17–24, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,895 ($271/night)
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Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($414/night)
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,300 ($471/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 18–23, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,578 ($285/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 18–28, 2025 (10 nights)
- 2 bed/2 bath, sleeps 8
- $7,056 ($645/night)
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Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 18–23, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($440/night)
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,500 ($500/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,061 ($660/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 18–23, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,578 ($285/night)
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Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($486/night)
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,600 ($514/night)