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)
Verified & Protected Voted Top Pick 2024

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 Voted Top Pick 2024

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 Voted Top Pick 2024

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 Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Voted Top Pick 2024

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)
Verified & Protected

Marriott's SurfWatch

Hilton Head Island, South Carolina
  • May 17–24, 2025 (7 nights)
  • 2 bed/2 bath, sleeps 8
  • $3,295 ($429/night)
Verified & Protected

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Voted Top Pick 2024

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)
Verified & Protected Voted Top Pick 2024

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)
Verified & Protected

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)
Verified & Protected Voted Top Pick 2024

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)
Voted Top Pick 2024

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)