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 2026
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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Voted Top Pick 2026
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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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 Heritage Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/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
- $2,750 ($393/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
- $1,769 ($253/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/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
- $2,428 ($347/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
- $3,404 ($486/night)
Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,878 ($268/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/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)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Voted Top Pick 2026
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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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,004 ($572/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,685 ($384/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
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Voted Top Pick 2026
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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Voted Top Pick 2026
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)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/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)
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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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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,329 ($266/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 17–22, 2026 (5 nights)
- 3 bed/3 bath, sleeps 12
- $2,636 ($527/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 2026
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
- $4,167 ($595/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- May 22–27, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,654 ($331/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 22–27, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($310/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/night)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–28, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($549/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,508 ($501/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,649 ($521/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)
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Marriott's SurfWatch
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,894 ($556/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
- $3,949 ($564/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
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Voted Top Pick 2026
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- May 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted Top Pick 2026
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)