Rentals with a Pool
Whether you're looking for a private pool to relax in your own oasis or a community pool perfect for family fun, our Hilton Head vacation rentals offer the best of both worlds. Cool off after a day at the beach, lounge poolside with a good book, or take an evening dip under the stars—your perfect getaway starts here!
15 properties available
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
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
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 Vacation Oasis on North Forest Beach7 Bedrooms | 5.5 Bathrooms | Sleeps 22 | Stunning BackyardLooking for a vacation home with a spectacular outdoor space? Look no further than 16 Mallard St in North Forest Beach! This stunning 7-bedroom, 5.5-bathroom home boasts the best backyard on the island, including a huge private pool and
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
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
Stunning Lagoon-View Home in Palmetto Dunes7 Bedrooms | 6.5 Bathrooms | Sleeps 18 | Private Pool | Golf SimulatorLooking for a vacation home that offers something for everyone in the family? Look no further than 25 Starboard Tack in Palmetto Dunes.This stunning home boasts spacious living areas and multiple bedroom wings, perfect for families or mu
Oceanfront Luxury Home on North Forest Beach5 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 vacation home offers the perfect blend of privacy and c
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
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
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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