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- Jun 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,202 ($440/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,614 ($523/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,178 ($436/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,057 ($676/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($658/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Jun 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Jun 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($376/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($659/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,201 ($743/night)
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Spinnaker at Shipyard
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,641 ($377/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,644 ($521/night)
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Royal Dunes Resort
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,968 ($424/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,403 ($486/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($576/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($576/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,993 ($570/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
Verified & Protected
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Jun 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,249 ($375/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Jun 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,204 ($441/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Jun 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,649 ($330/night)
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,393 ($566/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Royal Dunes Resort
Hilton Head Island, South Carolina- Jun 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)