Hilton Head Island in the heart of South Carolina’s Lowcountry offers 12 miles (19 kilometers) of coastline and all that you need to unwind, from relaxing on the beach or playing a round of golf to exploring the island by bike or going on a sunset cruise. Planning a weekend trip to Hilton Head Island for your family or group? A vacation rental offering privacy, convenience, and space to spare is your best choice. From beach house rentals to luxury resorts, this island has a wide array of vacation accommodations. Here is our list of vacation rentals with private pool in Hilton Head Island, South Carolina.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.
1. Gorgeous vacation rental by the beach (from USD 518)
Set just a few minutes from the beach, this gorgeous vacation rental offers accommodation that is good for up to 12 people. It has a large living space with five bedrooms and four bathrooms. You will fall in love with the bright and airy living room that is open to the elegant dining area. There is also a sunny breakfast area where you can have light meals or coffee breaks.
Outside the house is the lovely heated pool with a spill-over spa, perfect for your fun and relaxation time. Then, there is a deck with outdoor furniture and a dining area, as well as a porch with loungers where you can hang out and get tanned.
Top guest reviews
Cleanliness:
nicely appointed clean and quiet locationthe property was clean and worked perfectly for our family of 11Host:
owner provided good instructions/directionsgreat correspondence with ownervery responsive and helpful ownercouldn't say enough nice things about the owner highly highly recommend this homethe owner gordon was very accommodating and we truly had a wonderful experienceRead more reviewsLocation:
this house was literally 4 blocks (at the most) away it was the perfect location for our familythe house was in a great location
2. Spectacular home with a lovely backyard (from USD 325)
Take your family and friends on a vacation in this spectacular home. With its four cozy bedrooms and five beds, it can sleep up to ten guests comfortably. The rental features a lovely backyard with a private pool where you can go swimming or lounging under the sun.
Inside is an open-floor living area with a fully equipped kitchen and plenty of spaces for seating. Meanwhile, there are two dining areas, one with a wall-mounted TV and overlooks the backyard.
Top guest reviews
Amenities & Room:
the house is impressive and beautiful but still managed to be comfortableCleanliness:
clean beautiful and wonderfully locatedHost:
owners were very informative and responsive to all my questionsgreat owner made our stay very easyowner was very helpful and showed great pride in the propertythe owners were easy to work with and he communicated a nice overview of the home prior to arrivalowner could not have been better to deal with hope to return again next yearRead more reviewsLocation:
the location was perfectlocation was awesome and walking distance to harbour towngreat location and space for a golf tripgreat location and a wonderful overall experiencegreat property perfect location for up to 10
3. Luxurious beach mansion with hot tub (from USD 1063)
Enjoy sweeping views of the Atlantic Ocean in this luxurious Airbnb in Hilton Head Island with a private pool. This vacation rental has five bedrooms, 5.5 bathrooms, two laundry rooms, a six-car garage, a driveway for six more cars, and a private boardwalk to Shipyard Beach. The fully furnished and equipped master suites and bedrooms inside provide a comfortable stay for everyone.
Multi-generational families with mobility-challenged family members, on the other hand, will appreciate the elevator that services the garage and two floors of the house. Take a relaxing dip in the heated swimming pool, spa hot tub, or hot tub, or lounge and sip a cold drink by the tiki bar.
Top guest reviews
Amenities & Room:
the pool deck is awesome with a tiki bar that has its own fridge television and sound systemthis was a gorgeous home with a great pool hot tub and deck and just steps from the beachthere’s plenty of room for a crowd and the beds were very comfortablethe private pool and deck were quiet and relaxing and the private boardwalk to the beach was unrealCleanliness:
this made our vacation the first thing we noticed when we entered the home was how clean it smelledHost:
the owners are very nice and eager to please their guestsour hosts were fantastic thanks for a great weekbeautiful home with an easy to work with host is all you cancan hope for when rentingRead more reviewsLocation:
it’s a great location and house to staythe house was fantastic clean and a great location with a short walk to the beachexcellent location and very cleanthis house has tons of space and is in a fantastic locationamazing places to spend during a pandemic
Superhost
4. Well-furnished sanctuary near the beach (from USD 712)
This Vrbo in Hilton Head Island with a pool is in a quiet residential neighborhood and is a 10-minute walk from the beach. The sanctuary features an open layout with a large dining room, living area, newly updated kitchen, and two master suites. The four-bedroom, 4.5-bathroom home accommodates up to 12 guests and it is tastefully decorated with nature-inspired furnishings and accessories.
There are two garages, a private pool, and an ample yard surrounded by lush greenery. Expansive windows offer refreshing views of the poolside. Spend a few hours by the patio or head out for a round of kayaking, canoeing, or biking.
5. Wonderful island retreat (from USD 390)
This wonderful island retreat is nestled in the heart of Hilton Head Island. The vacation rental is lavishly flanked by stone lions, laid out in an open floor plan, and beautifully decorated with upscale furnishings personally chosen by its owners. The beach is a 5-minute drive or 20-minute walk. Also, there are nearby bike trails, shopping centers, and restaurants. It’s an exceptional location for anyone looking for an island getaway. Dive into the heated pool, sit on a deck chair, or relax in one of the two swings. Cap your day with a poolside barbecue.
Top guest reviews
Amenities & Room:
pool and grill were wonderful amenitiesour bachelorette group had a blast and the pool was perfectthe bedrooms were each made comfortable with linens and tvs in two out of the three roomsour family loved the heated poolmy son enjoyed his school zoom classes next to the pool and then jumping in right afterwardsCleanliness:
very clean and stylishhouse was clean and within minutes of everythingvery clean very well thought outhouse was very clean and there were plenty of towels and blanketsthe pool was clean and seemed to be cleaned frequently during our stayHost:
host was excellent at responding quicklythe host was awesome and responded quickly to any questionshost is extremely responsivethe host is very responsive and accommodatingshe is very responsive - an awesome hostRead more reviewsLocation:
the location is greatthe location is perfect close to burke's beach eating places and shoppingclose to the beach and many island attractionseverything is in really good shape and close to grocery storesbeautiful home in a great location
6. Country cottage with deluxe pool (from USD 621)
Relax in 2,400 square feet (223 square meters) of rustic living and entertainment space in this summer country home that sleeps 10. This charming two-story vacation rental with a loft has a great room, a fully stocked kitchen, a bar area, and a master suite. Two of the bedrooms upstairs have private balconies that are perfect for enjoying your morning coffee or glass of wine. This rental is less than two minutes away from the Hilton Head Island coastline. Step out onto the split-level patio and deck, where a luxurious spa-inspired pool awaits you.
Top guest reviews
Amenities & Room:
outside pool area had lots of space around it and great beach accessCleanliness:
the vacation rental was very cleanthe vacation rental was very cleanclean spacious everything worked in home kitchen well equipped nice locationHost:
rating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulRead more reviewsLocation:
house and location are greatvery spacious great locationit is beautiful spacious and so close to the beachit is super close to the beach and is surrounded by great biking trailsreviewer comments:great location seconds to the beach and plenty of room for our family
7. Upscale hideaway with hot tub in Shipyard Plantation (from USD 600)
Get away from it all in this first-class vacation rental in the gated community of Shipyard Plantation on Hilton Head Island. The four-bedroom, three-bathroom hideaway accommodates up to 10 guests, perfect for groups of friends or large families. Nestled in a quiet neighborhood surrounded by soaring trees, this lovely rental is part of South Carolina’s Lowcountry known for its marsh views, cultural heritage, and historic architecture. With a waterfall pool with a spa hot tub and a wide-open patio, this newly refurbished home is bordered by palm trees and tropical plants, ensuring peace and privacy. Grill some steaks, hotdogs, or burgers by the poolside. Relax in one of the themed bedrooms carefully decorated with touches of navy blue, forest green, or salmon pink.
Top guest reviews
Amenities & Room:
great property with a well equipped kitchenCleanliness:
just wasn’t that clean both inside and outsideRead more reviewsLocation:
perfect location on the islandshipyard is great locationthis house is amazing perfect location
8. Charming getaway with views of the freshwater lagoon (from USD 416)
Perfect for up to 16 guests, 62 Sandcastle Court has 5 bedrooms, 4.5 bathrooms, and a private heated pool with a sizable patio and deck. This four-story home is located in Sandcastles By the Sea, a boutique residential community just a few minutes away from Folly Field Beach. The vacation rental has spacious verandas with views of a freshwater lagoon, where you can try catch-and-release fishing. Each space is warmly decorated with contemporary furnishings inspired by the sea. Your beach community experience includes access to Xplorie, a provider of fantastic vacation experiences. Through Xplorie, play a round of golf or mini-golf, or try the adventurous zip line.
Top guest reviews
Amenities & Room:
beautifully decorated rooms with full amenities on every levelgreat house a lot of room for large familiesfortunately the house had a heated pool which really saved the vacation experienceCleanliness:
lots of beds and very cleanbeautifully decorated and very clean would go back for surehome was spacious and cleanbeautiful place a sweet and easy walk to the beach a light clean space and well appointedHost:
our host was very responsivethe host was very responsivecould gave had more with us management was easy to contact and quickly responsivethis house was beautifully appointed the host was extremely responsive and the location to the beach was perfectRead more reviewsLocation:
amazing home in a great location that is close to shopping beach and morei do wish it was closer to the beach especially traveling with childrenlots of space for everyone easy walk to the beach and plenty of sand toyssuch a great space for a large group with an easy short walk to the beachthe whole neighborhood is very quiet and we enjoyed five nights decompressing
9. Cozy retreat with private pool and patio (from USD 289)
Ideal for a group of eight, this cozy retreat on North Sea Pines Drive has three bedrooms and four baths. This lovely and charming vacation home has a private pool and fenced patio, as well as a quiet path to Hilton Head Island’s famous white-sand beaches. The open floor plan, fully equipped kitchen, and stylish furnishings make this vacation rental great for a family trip or a weekend escapade with friends. Explore the Sea Pines Forest Reserve or bike to Harbor Town for shopping, sailing, and watersports. Your stay at Sea Pines includes a free pass to the fitness center, where you can join scheduled classes or try aerobic equipment and weights.
Top guest reviews
Amenities & Room:
great pool backyard and lovely courtyardthe kitchen is better stocked than any house we have ever rentedCleanliness:
clean house with zero bugs seenclean and tidy seen a couple of bugs which is to be expected nothing out of the ordinaryplenty of room and very cleanRead more reviewsLocation:
great location in sea pinesperfect access to the beach 2 minute walk great locationa great quiet location for a family vacationgreat house in a great location in sea pinesgreat place and close to the beach 2 minute walk
10. Lovely townhouse with ocean views (from USD 682)
Perfect for up to 10 guests, 95 Singleton Beach is a grand Hilton Head Island oceanfront rental with a pool, an elevator, 2-door garage, 4 bedrooms, and 4.5 baths. This designer home features two floors of terraces overlooking the marsh and the ocean.
What makes this vacation rental truly unique is that it has both an indoor and an outdoor pool - enjoy a few laps in the water at any time of the year! After a long day at the beach, play a round of shuffleboard or grill some summertime favorites. Included in your stay is the signature Southern Hospitality Pass, which gives you exclusive access to golf, biking, and mini-golf facilities.
Top guest reviews
Cleanliness:
house exactly as described very clean and well equippedperfect for my group of 8 clean as described and very convenientthe vacation rental was very cleanreviewer comments:the home was beautiful and clean with plenty of room for our family of 10the house was clean and exactly as it was described and the rental company was responsiveHost:
the management company was super helpful & responsivethe management company was very responsive when we did reach outmanagement is very helpful accommodating and quick to respondloved the home great staff at vhhh very helpful ladiesrating details:the property manager was very helpfulRead more reviewsLocation:
the location was wonderful - very short walk to the beachthe house is in a perfect location with just a short walk to the beachbeautiful immaculate home and perfect location for our family vacationit was beautiful and the location so close to the beach was perfectreviewer comments:great rental good location
11. Spacious manor with hot tub (from USD 950)
Looking for a Hilton Head Island home that is big on both luxury and amenities? Sandhill Crane in the Sea Pines residential gated community boasts 4,250 square feet (395 square meters) of elegant space. This vacation rental can fit up to 18 travelers in its 6 bedrooms and 6 bathrooms. Sandhill Crane features a private heated pool and hot tub. The island manor is steps away from a vast, beautiful, and most importantly, uncrowded seashore. Sea Pines Beach Club is just a 10-minute stroll away, and golf courses are all within a 5-minute drive. Feel refreshed after a whole day at the beach, golf course, or tennis court.
Top guest reviews
Cleanliness:
the house was very clean great location and owners had excellent communication with usHost:
house is as beautiful as the pictures owner very responsive to all communicationRead more reviewsLocation:
great house and location but cumbersome parking arealoved the location to the beach had a great time
12. Roomy plantation home with ocean views
This six-bedroom, six-bathroom plantation home has a loft, bunk bedroom, home theater zone, game area, and private pool. The luxury ocean hideaway is fronted by stunning balconies and a soothing pool deck. This three-story home with two separate garages is ideal for groups of up to 16 guests. You’ll also enjoy calming views of Burkes Beach from here. 7 Sea Front Lane is close to the community beach path, so heading to the shoreline is easy and convenient. The property is also adjacent to Chaplin Community Park, which offers walking and biking paths and sports playing fields.
Hilton Head Island, South Carolina, United States
7.76 km (4.9 mi) from Coligny Beach ParkAccommodates: 16
Top guest reviews
Amenities & Room:
all of the bedrooms are very spacious with nice bathrooms and huge closetsthe movie room is perfect for watching movies or sports and they have a card table as wellthe bedrooms are spacious and comfortable with multiple sleeping optionsgiant tvs in every room easy access to cable or streamingalso the extra sitting/tv room upstairs would be a nice spot for kids to play insideCleanliness:
the house was perfectly cleaned when we arrivednice clean place to stay with a large grouphouse was very spacious clean and accommodated our entire grouptons of space and bathrooms and kitchen were very cleanHost:
david was a very gracious hostdavid was a great host throughout our stay at his beautiful homedavid was a great host that made sure we were taken care of throughout the entire processthe owner was very easy to get ahold of and helpfulamazing house and david was very responsive and helpfulRead more reviewsLocation:
great house and location nearby the beachbeautiful home and very close to the beachgood location on the island to get around to other places toothe location is easy to access and has tons to offer in the areathe close proximity to the beach was so nice too
Escape the stresses of daily life
Imagine having your own oceanfront home away from home on Hilton Head Island, South Carolina. Hilton Head Island is where you can get away from the stress of daily life. It’s also a home base for your golf excursions or a haven where you can make family memories. Experience peace and tranquility, taste Southern comfort food and mouth-watering classics and shop for that perfect something in this awarded destination. Our curated collection of Hilton Head Island homes offer access to the Atlantic Ocean and private pools. No matter where you’re staying, you will find a relaxing escape in Hilton Head Island, South Carolina.
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8 Best Luxury Resorts In Hilton Head Island, South Carolina - Updated 2024Virginia Maryann Dcruz -
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