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 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)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $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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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,004 ($572/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)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($430/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,439 ($288/night)
Voted Top Pick 2025
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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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($441/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($332/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,042 ($577/night)
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Voted Top Pick 2025
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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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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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,968 ($424/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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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/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)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($284/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 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 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,004 ($572/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
- $2,859 ($408/night)
Verified & Protected
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,240 ($463/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,957 ($422/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,439 ($288/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($418/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,219 ($244/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 17–23, 2026 (6 nights)
- 3 bed/3 bath, sleeps 12
- $3,404 ($567/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($550/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,835 ($548/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,916 ($559/night)
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Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($485/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($441/night)
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Island Links Resort
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $2,091 ($299/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($418/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($531/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($531/night)
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Voted Top Pick 2025
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,385 ($626/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
Verified & Protected
Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–28, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($549/night)