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
This 4 bedroom, 4 bath vacation home in Forest Beach HHI will enhance every second of your vacation on Hilton Head Island. Located 2 blocks from the beach, 2 Egret sets the tone for a luxury vacation with ample amenities and comforts. This home features all new wood flooring, paint, furniture, bathrooms, kitchen and more! Egret 2 has an open flo
Hot HOT 36
Bedrooms 4 bedrooms
Bathrooms 4 full baths
Guests 11 guests
Rating 5 (31)
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)
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)
4 Canvasback is a 3-bedroom, 3-bathroom Sea Pines Hilton Head Island home located on the beach path, just a 5-minute walk from the Atlantic Ocean, with a private pool! Located just inside the ocean gate of Sea Pines, this home offers two living areas, multiple decks with plenty of seating for outdoor dining, an open-concept floor plan, and a Lowcou
Hot HOT 33
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (11)
If you want luxury, space and a Hilton Head home rental that will accommodate your furry friend, then this is the perfect place for your next family vacation. Off Shore 63 is a 4 bedroom, 3.5 bathroom pet-friendly Palmetto Dunes home in a prime location on Hilton Head Island. High cathedral ceilings welcome you openly once you step into the entry f
Hot HOT 37
Bedrooms 4 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 13 guests
Rating 5 (13)
This 4-bedroom, 4-bathroom Hilton Head Island Sea Pines villa is located just outside of South Beach in Sea Pines. With stunning updates throughout, with a pool and jacuzzi located in the center of the home, this home provides guests with comfort and relaxation.The large living area, which is open to the dining room, features a large sectional sofa
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 4 full baths
Guests 10 guests
Rating 5 (9)
Escape to this beautiful home offering a serene retreat for your next Hilton Head getaway! The house offers relaxing golf and lagoon views, a pool, jetted hot tub, three bedrooms, three full baths and a loft with pull-out couch. It comfortably sleeps ten. From the entry, the coastal feeling dining room is to your right. With seating for six and a l
Hot HOT 45
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (40)
Enjoy being steps away from the beach and centrally located in Forest Beach while staying at 5 Egret! This gorgeous 6 bedroom home has recently undergone renovations and upgrades, including new furnishings, as well as interior and exterior painting.The main living areas of the home are located on the first floor with an open living area, dining are
Hot HOT 31
Bedrooms 6 bedrooms
Bathrooms 6 full baths 1 half bath
Guests 18 guests
Rating 5 (13)
*Pool Heat is available seasonally for an additional fee. The owner of the home is offering FREE pool heat (up to 80 degrees) seasonally each year from March - May and September - November. Please note- should the air temperature go below 55 degrees, the pool heater may not be able to maintain temperature.82 Kingston Dunes offers lowcountry living
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 5 (35)
Rest and relaxation await at South Live Oak 25, surrounded by tranquil lagoons on Hilton Head Island! This beautifully renovated 4-bedroom, 4-bathroom Hilton Head Sea Pines home offers a spacious open floor plan and a fantastic outdoor area, perfect for family gatherings. This stair-free home provides vacationers with two living areas, wood and til
Hot HOT 28
Bedrooms 4 bedrooms
Bathrooms 4 full baths
Guests 13 guests
Rating 5 (14)
This charming 3 bedroom, 3 bath pet-friendly Shipyard home is located in Hilton Head Island’s Shipyard less than a mile from the beach with a private pool! The perfect Hilton Head home villa rental with the comforts and privacy of a home rather than a crowded Hilton Head hotel room. The living room features a sofa, and loveseat in an ocean blue, a
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (18)
This beautiful 3 bedroom, 3 bathroom Hilton Head Shipyard rental home offers all the comforts you'd desire for a relaxing getaway. Located in Shipyard on Hilton Head Island, Kingston Dunes 80 offers all the comforts of home in a tranquil setting, less than a mile from the beach.The living area is outfitted with comfortable furnishings, a wall-mount
Hot HOT 43
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 5 (18)

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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.