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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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,422 ($346/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,022 ($432/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Port O'Call
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,440 ($206/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Apr 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Apr 19–25, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($912/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Apr 19–25, 2026 (6 nights)
- 3 bed/3 bath, sleeps 12
- $4,930 ($822/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Apr 20–25, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($637/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Apr 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($550/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- Apr 24–30, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($458/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Apr 25 – May 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Apr 25–29, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($442/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Apr 25 – May 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- Apr 25 – May 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,453 ($493/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Apr 25–30, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,220 ($244/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Apr 25 – May 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Apr 26 – May 3, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,268 ($467/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Apr 26 – May 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,800 ($971/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Apr 26 – May 1, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,341 ($468/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Apr 26 – May 2, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($586/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- Apr 26 – May 1, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,439 ($288/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Apr 26 – May 1, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,219 ($244/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Apr 27 – May 3, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($404/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,132 ($447/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
- $3,840 ($549/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
- $3,404 ($486/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Ocean Oak Resort by Hilton Grand Vacations
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/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
- $1,219 ($244/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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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 3–8, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,110 ($222/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 3–8, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,439 ($288/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/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
- $3,295 ($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
- $3,077 ($440/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
- $3,077 ($440/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
- $2,696 ($385/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 SurfWatch
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)