Homes with Private Pools | Hilton Head Island

Beat the hot summer weather on Hilton Head Island with a premium Hilton Head house rental with a pool. These popular properties offer the ultimate private outdoor amenity, perfect for sunbathing, entertaining the kids, and enjoying the outdoors in comfort. A private pool adds essential luxury and privacy to your stay, transforming afternoon downtime into a refreshing, memorable experience. For the best coastal getaway, secure one of these highly sought-after Hilton Head Island vacation rentals. Our selection of Hilton Head vacation rentals with pools ensures you maximize your fun and relaxation. Plan your trip today and get ready to enjoy endless, sunny afternoons by your private pool.


Properties Available 53 properties available
2 Lookout in Hilton Head's Palmetto Dunes Resort area will be your family's next premier vacation destination. The owners of this home completed an extensive renovation and redecorating in the Spring of 2023. This home offers a spectacular outdoor space, unparalleled amenities and is located just a 3-5 minute walk to the beach! This spacious and b
Hot HOT 28
Bedrooms 5 bedrooms
Bathrooms 4 full baths
Guests 15 guests
Rating 5 (8)
Did you know the perfect vacation home really does exist and it's on Hilton Head Island?! Full Sweep 60 is a luxury 4 bedroom, 3 bathroom, fully remodeled home that offers comfort and style with all the modern conveniences you could hope for. With amenities like a private pool and an electric car charger in the garage, this home provides the perfec
Hot HOT 19
Bedrooms 4 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 4.9 (17)
70 North Sea Pines is an ample home providing room for a large group at a great value. This 6-bedroom, plus a bunk room, 4.5-bathroom home features a ground-level entry, with no stairs to enter, a private pool and just a 5-minute walk to the beach! No step entry from the driveway into the first floor, where the living area, dining area, kitchen
Hot HOT 22
Bedrooms 6 bedrooms
Bathrooms 4 full baths 1 half bath
Guests 14 guests
Rating 5 (4)
29 Rum Row offers tranquil glimpses of the Robert Trent Jones golf course, a picturesque backyard, a sun-drenched pool deck, and all the things that you will need for an unforgettable Hilton Head Island adventure. Just off the outskirts of this Palmetto Dunes home is a screened porch accented by vaulted wood ceilings and furnished with a seagrass p
Hot HOT 40
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 11 guests
Rating 5 (28)
Look no further for your next family vacation home! 36 Kingston is a stunning 4 bedroom, 3 bathroom Shipyard Hilton Head pet-friendly rental with a private pool! This spacious home with an open floor plan features 2 living areas and a fantastic kitchen. With separate wings of the home on either side of the living areas, this 36 Kingston is perfect
Hot HOT 48
Bedrooms 4 bedrooms
Bathrooms 3 full baths
Guests 9 guests
Rating 5 (25)
51 Forest Drive is a luxury home that has been completely renovated and newly furnished with ample amenities inside and out!The main level of the home features a comfortable and well-appointed living area with plush furniture and a Smart TV. There is also a powder room for added convenience. Through the living area, you'll find the gourmet kitchen
Specials Tag Special
Beach Renourishment Project

A beach renourishment project is currently underway near this property and will continue through the summer. Please contact our Guest Services team at 843-785-6767 or follow this link for additional information. If this message is still active, the project in this area is expected or ongoing. Thank you for your understanding as we preserve our gorgeous beaches!

Bedrooms 4 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 12 guests
Rating 5 (20)
Located on the 13th Fairway of Harbour Town Golf Links in the historic Sea Pine Plantation, this 3 bedroom, 2.5 bathroom pet-friendly Hilton Head vacation rental boasts an expansive backyard with a screened-in pool only 1.5 miles to the Atlantic ocean. The perfect getaway spot for your entire family’s next vacation on Hilton Head Island, SC. The co
Hot HOT 62
Bedrooms 3 bedrooms
Bathrooms 2 full baths 1 half bath
Guests 8 guests
Rating 5 (9)
If you're searching for fully updated vacation rentals on Hilton Head, SC with lots of space, amazing views, a large pool and close to the beach then look no further. This 7 bedroom, 6.5 bathroom Hilton Head SC home is located on a quiet private cul-de-sac in Palmetto Dunes Resort with views of both the 11-mile lagoon system and the Robert Trent Jo
Hot HOT 32
Bedrooms 7 bedrooms
Bathrooms 6 full baths 1 half bath
Guests 23 guests
23 West Beach Lagoon is a Hilton Head Sea Pines home overlooking one of the many lagoons, close to the beach with a private pool and great gathering space.As you walk in the front door, you’ll be greeted by an open-concept floor plan, views of the pool and patio beyond, new décor and furnishings, as well as luxury vinyl plank flooring that spans th
Hot HOT 38
Bedrooms 4 bedrooms
Bathrooms 4 full baths 1 half bath
Guests 10 guests
Rating 5 (26)
This 5 bedroom, 5.5 bath, single-family Singleton Beach home will be an island oasis that you won't want to leave! This well-equipped home features a private pool, designer decor, and state-of-the-art appliances, as well as double garages and a wide driveway.The first-floor pool level features a cozy sitting room decorated with a tropical motif. **
Hot HOT 32
Bedrooms 5 bedrooms
Bathrooms 5 full baths 1 half bath
Guests 12 guests
Rating 5 (8)
Make cherished memories that will last forever when you treat your family to an island vacation in this 4 bedroom, 3 bathroom Hilton head home for rent in the beautiful Shipyard. Gloucester 79 is a beautiful Shipyard home that will not disappoint!Upon entering the home you will be greeted by a southern style front porch complete with rocking chairs
Hot HOT 24
Bedrooms 4 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (9)
40 Red Oak is a spacious, meticulously appointed 4-bedroom, 3.5-bathroom home, ideally located near Harbour Town and the famed 12th and 13th holes of the Harbour Town Golf Course. Completely renovated in 2024, this home has all the comforts you’d expect from a premier Hilton Head vacation rental. The main level of the home has an open-concept livin
Specials Tag Special
Beach Renourishment Project

A beach renourishment project is currently underway near this property and will continue through the summer. Please contact our Guest Services team at 843-785-6767 or follow this link for additional information. If this message is still active, the project in this area is expected or ongoing. Thank you for your understanding as we preserve our gorgeous beaches!

Bedrooms 4 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 10 guests
Rating 5 (5)

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Hilton Head Island Vacation Rentals With Pool FAQs:

How does a home with a pool boost relaxation on Hilton Head Island?

After a day on the beach or riding around Hilton Head Island, nothing’s quite as refreshing as coming home and slipping into the pool. You can wade in or simply unwind by the edge embracing the peace—just you, the sunny blue sky, and the tranquility of the moment.

A pool offers a quiet retreat away from the crowds and the rest of the island while remaining immersed in the island’s beauty of nature. Having a pool at your Hilton Head Island home means there’s more space for you to relax, enjoy the moment, and make the most of your vacation.

 

What convenience does a pool provide for families visiting Hilton Head Island?

A private pool redefines the way your family relaxes on Hilton Head. If the ocean isn’t ideal for the day, you can take the pressure off of having to go to the beach for time in the water. The kids can splash and play right at home, giving parents the freedom to relax knowing everyone’s within reach.

Breaks are easy, the snacks are close by, and no one’s asking, “can we leave yet?” The pool offers a refreshing change of pace. It’s family fun without the hassle.

Your family can set its own pace during your Hilton Head Island stay, with the pool becoming the best part of your vacation routine.

 

How does a private pool offer a distinct swimming experience on Hilton Head Island?

A private pool offers what the beach can’t: no crowds, no unpredictable ocean conditions, and no messy sand to clean up. The pool is always easy and convenient: calm, clean, and ready to use anytime.

Swim whenever you want, anytime you want, with no stress about the things you can’t control. You still get the water, the tranquility, and the space. Nestled among swaying palms and quiet skies, a private pool becomes a cherished memory from your Hilton Head stay.

 

What social perks come with a pool at a Hilton Head Island Home?

The pool becomes your in-house hangout spot, an easy way to connect without having to go anywhere at all. It’s where kids gather and make games on the fly, and grownups gather without needing a plan.

No need to reserve space, dodge crowds, or pack up and go to the car; you’re just moments away from the kitchen or the grill. Whether you’re hosting a casual get-together or a full-on party under the sun, the pool is guaranteed to keep everyone entertained.

With a private pool, time flows a little differently, and you don’t have to go far to feel connected.

 

How does a pool pair with Hilton Head Island’s warm weather for guests?

When the island’s temperature begins to rise (especially during the summer), a pool at home gives you a relaxing way to cool down without heading to the beach. It’s a great way to stay outdoors longer without the heat cut your time short.

And in the milder spring and fall seasons, the pool keeps the outdoors fresh. With a pool, guests can take the weather in stride and turn it into something to enjoy on Hilton Head Island. Swim, lounge, repeat—that's the agenda for your vacation.