Hilton Head Island Home Rentals
From oceanfront mansions that sleep 24 to charming 4-bedroom Sea Pines retreats — browse our curated selection of Hilton Head Island vacation home rentals. Perfect for large families, reunions, corporate retreats, and groups of every size. All properties managed by trusted local companies. Click any home for full details and availability on VRBO.
10 BD / 10 BA — New Oceanfront
New home! Spacious 10-bedroom oceanfront on Hilton Head Island — sleeps 24 in beds. An extraordinary vacation property for very large groups, reunions, and corporate retreats right on the ocean.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
8 BD / 6.5 BA — Close to Beach
Eight bedrooms close to the beach with ocean views — sleeps 28 in beds. An exceptional large-group vacation home that delivers space, comfort, and easy beach access on Hilton Head Island.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
83 Singleton — Ocean & Marsh Views
Incredible ocean and marsh views — sleeps 27. 83 Singleton is a premium large-group vacation home that delivers a truly stunning Lowcountry coastal experience.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
7 BD — Oceanview Home
7 bedroom oceanview home that sleeps 24 guests. A fantastic large-group vacation property with generous spaces, beautiful ocean views, and everything you need for an unforgettable Hilton Head getaway.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
29 Corine Ln — Luxury 3-Story
Luxury 3-story home near beach — 6 beds, 7 baths, sleeps 18. A stunning Hilton Head Island property with exceptional finishes and plenty of room for families and large groups.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
19 Crabline — Stunning Dream Home
Stunning 6-bedroom home in Hilton Head — a dream! Near beach. Beautifully designed and impeccably maintained, this property is perfect for groups who want the very best Hilton Head Island has to offer.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
2nd Row Ocean — Remodeled
2nd row ocean — completely remodeled with amazing ocean views! This fully updated 6-bedroom Hilton Head Island home delivers incredible views and modern comfort in one breathtaking package.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
41 Crabline — Singleton Beach
41 Crabline Court — Hilton Head Singleton Beach. Close to the beach and park — sleeps 20. A wonderful large-group home in one of Hilton Head Island’s most popular and convenient beach neighborhoods.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
12 Crabline — Rooftop Deck
12 Crabline Court — great for families and large groups with a rooftop deck and ocean view. One of Hilton Head Island’s best-positioned vacation homes for groups who want space and stunning views.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
26 Corrine Lane — Beach House
Fantastic beach house at 26 Corrine Lane — sleeps 21 in beds. A beloved Hilton Head Island property that delivers generous space, easy beach access, and everything you need for a perfect vacation.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
30 Corrine Lane — Near Beach
30 Corrine Lane — close to the beach and sleeps 21 in beds. A spacious and comfortable 5-bedroom Hilton Head Island home in a fantastic location, perfect for large families and groups.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
Exceptional Ocean Oriented Home
⭐⭐⭐⭐⭐ Exceptional ocean-oriented home! This top-rated 5-bedroom Hilton Head Island property is everything guests rave about — beautiful, spacious, and perfectly positioned for an incredible beach vacation.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
Private Beach House — Golf Cart Shuttle
Private beach house on Hilton Head Island — free golf cart beach shuttle during summer! An exceptional 5-bedroom property with a highly coveted private beach house feel and premium amenities.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
New Listing — Private Pool
New listing! Completely remodeled beach house with private pool — sleeps 22 in beds. A brand new Hilton Head Island vacation property with modern finishes and an incredible private pool.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
48 Crabline — Coastal Boho Pool
48 Crabline — coastal boho beach house with private pool near the beach and park. A beautifully styled 5-bedroom Hilton Head Island home with a unique coastal aesthetic and wonderful private pool.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
1 Loblolly — Sea Pines Hot Tub
1 Loblolly — 5-bedroom Sea Pines house with screened-in porch, hot tub, and heated pool. A premium Sea Pines Resort vacation home with exceptional amenities and the perfect Hilton Head Island setting.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
Short Walk to Ocean — Sleeps 20
Short walk to the ocean — perfect for large groups — sleeps 20 in beds. A wonderful 5-bedroom Hilton Head Island home in a great location with easy beach access for the whole group.
Managed by SINCERELY SOUTHERN HOSPITALITY, LLC
✉ hiltonheadtony@yahoo.com
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