Hilton Head Rentals with Private Pool
ENJOY A DREAM BEACH HOUSE WITH A POOL
Relaxing by the pool is a special part of visiting Hilton Head Island. 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.
Browse our Hilton Head Rentals with Pools!
62 properties available
40 Bradley Beach, freshly painted, 4 bedroom, 3 and a half 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 located next to Driessen Beach Town Park with playground equipment for the kids, comfort stations, and is just a four-minute
BACK ON THE RENTAL. MARKET & BETTER THAN EVER! This beautiful 4-bedroom 4.5- bathroom home is located in the heart of Singleton Beach and is just 300 feet to the ocean. This home overlooks the expansive marsh and also features amazing ocean views on every level. Guests will enjoy the huge pool, over-sized bedrooms, and the third-floor bonus room wh
Book a 7-night stay in August Receive One Night Free
95 Singleton Beach Road, located on Singleton Beach is a luxury, designer home featuring 4 bedrooms, 4.5 bathroom with ocean & marsh views just 400 feet to the beach! This beautiful 3 story home features two living spaces perfect for entertaining and coming together after a long day at the beach
1 Barrier Beach Cove is a brand new 6 bedroom, 5 1/2 bathroom home with a large private pool, just a quick walk to the beach and next to Chaplin Park (tennis, basketball, playground, baseball field). This property is built with a renter in mind, offering a chef\'s kitchen, large balconies, private pool and luxury finishes and decor.
Vacation Homes
This property is new to Vacation Homes of Hilton Head and has been fully updated with a brand-new furniture package throughout the entire house. 4 Catboat is offering an open concept floor plan with large bedrooms (each as its own bathroom) and an oversized private pool. If you enjoy being steps from the beach and close to all the amenities that th
44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 13 and has a large 16\' x 32\' pool, and features an outdoor fire pit perfect for a night hosting around the pool or a cool day in the fall! There is plenty of seating and the home is conveniently located at the very end of Bradley Road with a fenced in patio giving adde
Look no further than this NEW oceanfront oasis, 8 Terra Bella Trace, sure to wow your entire group. This six-bedroom, eight-bathroom home was finished in late-summer 2022 and leaves nothing spared. The chef\'s kitchen offers top of the line appliances and oversized island with seating has room for everyone to enjoy meals together. The open concept
This house received a complete make-over in 2021 to include a kitchen upgrade, new paint and flooring throughout, a new furniture package and updated decor. Best of all, this house is just one house away from the beach; the beach path is literally 50 feet away! Not only does this house have strong ocean and marsh views, it boasts 7 bedrooms, 5 1/2
This updated 6-bedroom house is in the prestigious private community of Palmetto Dunes and is just a hop skip and a jump away from the beach! This property offers an open layout perfect for large groups, spacious bedrooms, and a private pool that all ages will enjoy. Call us today to make 3 Sutherland Court yours!
Free Activities Included! Play a
This completely renovated oceanfront dream is located in the popular Burkes Beach Area. Enjoy the sprawling views from every floor! This 6 bedroom comes with FIVE KING bedrooms and a custom built bunk area for the kiddos to enjoy.
Free Activities Included! Play a round of golf, explore Hilton Head on bicycle and even bring out your inner kid with
**Recent renovations include: New paint throughout, new living furniture, new carpet upstairs, new flooring on first floor, new carpentry work throughout garage stairwell. Do not miss out on this newly renovated property! Looks like a brand new house!! **
This amazing 6-bedroom, 4.5-bathroom home is ideal for multiple families or larger groups loo
This updated oceanfront 6-bedroom/ 6.75-bathroom home is everything you have been looking for! With 2 living areas there is plenty of room for your group to have fun, spread out, and relax. Play pool in the top floor media room or practice your swing on the ground floor putting green. Vacationers will enjoy their own private pool (with access to a
Tell us what you're looking for and someone will contact you with available options.