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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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 30 – Jun 6, 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 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 30 – Jun 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($266/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,271 ($610/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($539/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,271 ($610/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,548 ($650/night)
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Bluewater Resort & Marina
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($386/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,478 ($496/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($550/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 31 – Jun 6, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($277/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,764 ($353/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,873 ($375/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 31 – Jun 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($496/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 31 – Jun 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- Jun 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,478 ($354/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 1–6, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($550/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 1–6, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($604/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Jun 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($300/night)
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 1–7, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($640/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 2–7, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($724/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 2–6, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($796/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 2–12, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($656/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,832 ($690/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- Jun 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,312 ($759/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $2,750 ($393/night)
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Waterside by Spinnaker
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
Verified & Protected
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,385 ($626/night)
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Jun 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)