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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Waterside by Spinnaker

Hilton Head Island, South Carolina
  • Apr 19–26, 2025 (7 nights)
  • 3 bed/3 bath, sleeps 8
  • $3,185 ($414/night)
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Marriott's SurfWatch

Hilton Head Island, South Carolina
  • Apr 19–26, 2025 (7 nights)
  • 3 bed/3 bath, sleeps 12
  • $3,568 ($464/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • Apr 19–26, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,295 ($429/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • Apr 19–26, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,096 ($271/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 19–26, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,749 ($357/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • Apr 19–25, 2025 (6 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,660 ($250/night)
Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 19–26, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,800 ($543/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • Apr 19–23, 2025 (4 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,150 ($488/night)
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Marriott's SurfWatch

Hilton Head Island, South Carolina
  • Apr 20–25, 2025 (5 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,205 ($400/night)

Marriott's SurfWatch

Hilton Head Island, South Carolina
  • Apr 20–26, 2025 (6 nights)
  • 3 bed/3 bath, sleeps 12
  • $5,500 ($917/night)
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Vacation Time of Hilton Head Island - Ocean Dunes

Hilton Head Island, South Carolina
  • Apr 20–27, 2025 (7 nights)
  • 1 bed/1 bath, sleeps 4
  • $1,769 ($229/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • Apr 20–27, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,240 ($421/night)
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Marriott's SurfWatch

Hilton Head Island, South Carolina
  • Apr 20–25, 2025 (5 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,069 ($375/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 20–27, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,859 ($371/night)
Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 20–26, 2025 (6 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,500 ($417/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 21–29, 2025 (8 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,940 ($449/night)

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • Apr 21–27, 2025 (6 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,200 ($533/night)
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Marriott's Harbour Club at Harbour Town

Hilton Head Island, South Carolina
  • Apr 21–26, 2025 (5 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,478 ($450/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 22–29, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $4,271 ($556/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 25 – May 2, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $4,603 ($600/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 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
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($500/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $4,058 ($529/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,077 ($400/night)
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Marriott's SurfWatch

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 3 bed/3 bath, sleeps 12
  • $3,458 ($450/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,220 ($157/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,840 ($500/night)
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Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,077 ($400/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,186 ($414/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,513 ($457/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $4,603 ($600/night)
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Marriott's SurfWatch

Hilton Head Island, South Carolina
  • Apr 26 – May 3, 2025 (7 nights)
  • 3 bed/3 bath, sleeps 12
  • $3,513 ($457/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 27 – May 4, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,859 ($371/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • Apr 27 – May 4, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,186 ($414/night)
Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 27 – May 4, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $2,795 ($399/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • Apr 27 – May 4, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,458 ($450/night)
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Ocean Oak Resort by Hilton Grand Vacations

Hilton Head Island, South Carolina
  • Apr 30 – May 7, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $2,641 ($343/night)
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Marriott's SurfWatch

Hilton Head Island, South Carolina
  • May 2–9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $4,930 ($643/night)
Verified & Protected Voted Top Pick 2024

Marriott's Barony Beach Club

Hilton Head Island, South Carolina
  • May 2–9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,458 ($450/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Hilton Head Island, South Carolina
  • May 2–9, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $1,396 ($180/night)
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Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina
  • May 3–10, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,240 ($421/night)
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Marriott's SurfWatch

Hilton Head Island, South Carolina
  • May 3–9, 2025 (6 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,186 ($483/night)

Port O'Call

Hilton Head Island, South Carolina
  • May 3–10, 2025 (7 nights)
  • 3 bed/3 bath, sleeps 8
  • $1,750 ($250/night)

Marriott's SurfWatch

Hilton Head Island, South Carolina
  • May 3–10, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,000 ($429/night)
Verified & Protected Voted Top Pick 2024

Marriott's Grande Ocean

Hilton Head Island, South Carolina
  • May 3–11, 2025 (8 nights)
  • 2 bed/2 bath, sleeps 8
  • $4,712 ($538/night)
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Marriott's Monarch at Sea Pines

Hilton Head Island, South Carolina
  • May 3–10, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 6
  • $3,840 ($500/night)

Waterside by Spinnaker

Hilton Head Island, South Carolina
  • May 3–10, 2025 (7 nights)
  • 3 bed/3 bath, sleeps 8
  • $1,650 ($236/night)
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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)