Hilton Head Vacation Rentals with Private Pools
Experience the ultimate Hilton Head getaway with a vacation rental that features a private pool. At Hilton Head Properties, we offer a selection of stunning homes and villas where you can relax, unwind, and enjoy the perfect blend of comfort and convenience
15 properties available
Private Family Retreat Near North Forest Beach4 Bedrooms | 3 Bathrooms | 10 Sleeps | Pet Friendly | Private Pool & SpaWalk up the street just 2 short blocks (3 minutes) to expansive North Forest Beach beach!This spacious home is on a quiet, family friendly street, with a neighborhood feel. Set on 1/3 acre, you have a fully private, fenced in ba
Stunning Second-Row Family Oasis in Palmetto Dunes6 Bedrooms | 6.5 BathroomsThis stunning new 2020 beach home is perfect for families looking for a memorable vacation. With six spacious bedrooms and top-of-the-line amenities, this home is sure to exceed your expectations. Featuring three master suites, it's ideal for multi-generational getaways
Luxurious Willow Oak Home in Sea Pines4 Bedrooms | 4.5 Bathrooms | Sleeps 12 | Private Pool & SpaWelcome to your luxurious vacation retreat nestled in prestigious Sea Pines. This exquisite vacation home offers the perfect blend of elegance, comfort, and convenience for your getaway. As you enter the home, you'll be greeted by an inviti
A Sea Pines Legacy Home for Longer Island Escapes5 Bedrooms | 5 Bathrooms | Sleeps 10 | Peaceful Backyard OasisLocated in the heart of Sea Pines on Hilton Head Island, The Hamilton is a beautifully furnished 5-bedroom, 5.5-bath legacy home available for extended monthly stays from November through April.With over 5,400 square feet of refined living
Stunning Golf-View Oasis in Palmetto Dunes4 Bedrooms | 4 Bathrooms | Sleeps 12 | Family Fun Game RoomExperience the ultimate beach vacation at this 4-bedroom getaway with an open layout and stunning golf course views.Just a few minutes bike or walk via bike pathways to the beautiful beaches in Palmetto Dunes. Recently upgraded with gorgeous fu
Oceanfront Beach Oasis in Sea Pines5 Bedrooms | 4 Bathrooms | Sleeps 14 | Ocean Views | Backyard OasisWelcome to 33 Ruddy Turnstone, an exceptional oceanfront vacation home located in the prestigious Sea Pines resort of Hilton Head Island. This stunning 5-bedroom, 4 full bath, and 2 half bath beach house offers the perfect blend of modern eleg
Oceanfront Luxury Home on North Forest BeachUNDER REMODEL - August 2026 – December 2027 5 Bedrooms | 3.5 Bathrooms | 13 Sleepers | Breathtaking Ocean ViewsWelcome to 19 Dune Lane, the perfect oceanfront vacation home for those seeking the ultimate island experience.Nestled in the heart of the North Forest Beach area, our oceanfront
Refined Coastal Living in Sea Pines4 Bedrooms | 4 Bathrooms | Sleeps 12 | Backyard Oasis with Private PoolWelcome to a truly exceptional vacation home in Sea Pines—a rare blend of timeless elegance and modern comfort, now part of the Hilton Head Properties R & R rental collection. This single-level residence has been exquisitely reim
Spacious Family Home on Singleton BeachNew Home Construction Next Door7 Bedrooms | 7.5 Bathrooms | Sleeps 18 | Ocean ViewsWelcome to your dream vacation home at Singleton Beach! This 7-bedroom, 7 ½-bathroom home is located in Hilton Head Island's newest and most exclusive community. As soon as you enter the home, you'll be greeted wi
Spacious Dog Friendly Home Located in Sea Pines4 Bedrooms | 3.5 Bathrooms | Sleeps 10 | Private Pool & SpaLooking for a prime location for your next vacation? Look no further than 16 Duck Hawk, located in the heart of Sea Pines on Hilton Head Island.Upon entering the home, you'll be greeted with an expansive living room that transitio
Your Beachside Oasis in Folly Field4 Bedrooms | 4 Bathrooms | Sleeps 14 | Private Pool & SpaWelcome to your dream getaway—a stunning, purpose-designed 4-bedroom beachside home in the heart of Hilton Head Island's beloved Folly Field neighborhood. Just steps from the pristine sands of a serene beach, this home promises a perfect b
Magnificent Luxury Retreat on North Forest Beach7 Bedrooms | 6.5 Bathrooms | Sleeps 14 | Beach GetawayEscape to the North Forest Beach area of Hilton Head Island and experience the ultimate beach vacation in this magnificent 7 bedroom, 6.5 bath home just 50 yards from the Atlantic Ocean. This custom-built retreat boasts 4500 square feet of lux
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