Hilton Head Rentals with Private Pool

Relaxing by the pool is a special part of visiting Hilton Head Island. Enjoy everything Hilton Head has to offer with our Hilton Head rentals with a private pool. Afternoons are hot, and when the sun is high in the sky, jumping into a refreshing pool feels like entering paradise. During your Hilton Head vacation, there’s no better place to hang out than your own private pool. Below you’ll find Hilton Head rentals with private pools. Our vacation rentals with private, heated pools place you in Hilton Head’s best communities. Hilton Head vacation homes with pools are perfect for families and groups. Plunge into an amazing vacation on Hilton Head Island with Vacation Homes of Hilton Head.


Properties Available 56 properties available
19 Singleton Beach Place, Hilton Head Island, is a 6 bedroom, 6.5 bathroom oceanfront home with a private pool and boardwalk, elevator, and chef's kitchen. This property offers a luxurious retreat for vacationers and includes up to $1000 in FREE activities with every reservation. The breathtaking ocean views, upscale finishes, and elegant d&eac
Hot HOT 47
19 Singleton Beach Place
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.8 (34)
12 Whelk Street is located on the gorgeous Bradley Beach. This property is a luxurious and recently renovated 5 bedroom, 5 bathroom with great ocean views and just 145 feet to the beach! This beautiful 4 story home has an open concept first level perfect for entertaining and coming together after a long day at the beach. This house also has ten bal
Hot HOT 25
12 Whelk Street
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.6 (39)
9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring views! Ideal for multiple families, this stunning seven-bedroom, five-and-a-half-bathroom home spans three stories with an elevator. Professionally decorated, it boasts breathtaking panoramic views from most rooms. Four oceanfront bedrooms feature private balco
Hot HOT 50
9 Singleton Beach Place
House
Bedrooms 7 bedrooms
Bathrooms 5 baths
Guests 20 guests
Rating 4.6 (8)
***EV Car charging outlet (receptacle) in Garage (guest to bring their own charging station)***This beautifully decorated 6 bedroom, 6 bath open concept home has three master bedroom suites with king beds and flat screen TVs. The master bathrooms are simply exquisite, with spa tubs, dual sinks, and separate frameless showers with lavish stone floor
Hot HOT 130
32 Corine Lane
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 15 guests
Rating 4.7 (24)
**Now offering 50% off pool heating fee for April 2024** Contact Vacation Homes of Hilton Head for more information **This is a beautiful brand new 5 bedroom home in Burkes Beach. 3-5 minute walk to the beach, right next to Chaplin Park (tennis, basketball, playground, and beautiful field), easy drive to local restaurants, bars and grocery stores.
Hot HOT 38
1 Shore Crest Lane
House
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 4.6 (3)
Wow! This AMAZING 3BR/2.5BA home is ready for your enjoyment! Nestled in a private, quiet areas of Palmetto Dunes, 47 Offshore Drive offers easy walking/biking access to Shelter Cove and Towne Center for dining, fishing, shopping, boating, etc. This home is also only 1 mile from door to sand. It has the desired open, updated, natural light concept
Hot HOT 52
47 Off Shore Dr
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 (15)
13 Moonshell, Hilton Head Island is a charming Hilton Head retreat that offers an ideal setting for your coastal escape. Featuring 4 bedrooms and 3 bathrooms, along with a spacious fenced backyard complete with a private pool and outdoor bar, this property is designed for relaxation and enjoyment. Conveniently located just a short 3-5 minute drive
Hot HOT 30
13 Moonshell Road
House
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 4.7 (50)
7 Periwinkle Lane, Hilton Head Island. Come experience beachside bliss at this charming 5-bedroom, 4.5-bathroom home, just a short 5-minute walk from the sandy shores. Completely remodeled, it boasts a gorgeous private pool for relaxation. Inside, a top-floor loft and all-new appliances await. Conveniently situated near a local park, restaurants, a
Hot HOT 59
7 Periwinkle Lane
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.6 (16)
This house features 5 bedrooms and 6 bathrooms with space enough for 16.Please review our property photos and our available amenities to make sure this rental is a perfect fit for your needs. We strive to keep this information as up-to-date as possible so you can feel confident in knowing what you are renting.We will send you all necessary pre-arri
Hot HOT 68
7 Abalone Lane
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 16 guests
Rating 5 (1)
1 Barrier Beach Cove, Hilton Head Island, is your ultimate vacation destination! Completed in 2023, this brand-new 6-bedroom, 6 1/2-bathroom residence offers a luxurious escape just moments from the beach. With a spacious private pool and spa, you can relax and unwind in style. Located adjacent to Chaplin Park, guests can enjoy easy access to ameni
Hot HOT 52
1 Barrier Beach Cove
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 5 (4)
42 Bradley Beach, a 6 bedroom, 4.5 bath home with private pool, offers not only a great mid island location, but is among our most value attractive properties for families and groups. This property is also located next to Driessen Beach Town Park with playground equipment for the kids, comfort stations, and is just a four-minute walk to the beach o
Hot HOT 71
42 Bradley Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.7 (20)
You will feel very welcome at the home as it includes a partial view of the ocean from the front porch. Head into the main level of the house and you will enter a the great room, including stunning travertine tile floors, a fully-equipped kitchen with stainless steel appliances, and granite counter tops. This home also offers two decks, overlooking
Hot HOT 22
37 Bradley Circle
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 14 guests
Rating 4.5 (7)

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