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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Players Club of Hilton Head Island
Hilton Head Island, South Carolina- Apr 29 – May 3, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $888 ($222/night)
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,848 ($407/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 2–7, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,478 ($496/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,550 ($221/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,550 ($221/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,295 ($471/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 2–6, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($851/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 3–8, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,096 ($419/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,362 ($623/night)
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,505 ($358/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 3–8, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($572/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 3–8, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,549 ($310/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($408/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,676 ($525/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 9–16, 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- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,022 ($432/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,786 ($541/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,714 ($245/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,291 ($470/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 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- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,851 ($370/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 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- May 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,967 ($593/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 12–24, 2026 (12 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($184/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 14–17, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $3,294 ($1,098/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,230 ($461/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,478 ($354/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,512 ($502/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,660 ($237/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,731 ($533/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)