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 54 properties available
32 Crabline Court is an exquisitely decorated 5 bedroom, 4 bathroom home located in Hilton Head’s Singleton Beach rentals area. It offers a short walk, or bike ride, to Singleton Beach as well as quick access to the beautiful Chaplin Park, shops, restaurants and Hilton Head attractions and activities.Approximately 10 steps up lead to the porch, a g
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Bradley Circle Resurfacing

Beaufort County will be resurfacing Bradley Circle and Burkes Beach road on Hilton Head, starting on September 9th thru September 11th Weather permitting.

Signage will be posted.  Traffic flow and parking should not be interrupted.  Please feel free to call if you have any questions.


Bedrooms 5 bedrooms
Bathrooms 4 full baths
Guests 12 guests
Rating 5 (17)
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 25
Bedrooms 6 bedrooms
Bathrooms 6 full baths 1 half bath
Guests 18 guests
Rating 5 (16)
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 23
Bedrooms 6 bedrooms
Bathrooms 4 full baths 1 half bath
Guests 14 guests
Rating 5 (5)
Experience Hilton Head Island in luxury and comfort when you stay in this beautiful, 3 bedroom, 3.5 bath, Palmetto Dunes vacation home on Hilton Head Island. Beveled glass double entry doors make a distinctive first impression as you enter a home where the decor is a perfect blend of old and new, highlighted by original artwork and natural outdoor
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 8 guests
8 Governors Lane is where southern charm meets modern comfort. This beautifully renovated and newly outfitted 3 bedroom, 2.5 bathroom home offers a spacious, open floor plan, luxurious accomodations and a brand new pool and spa for the 2026 season!The living area is comfortably furnished and offers a large Smart TV. The space extends to a sun room
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 2 full baths 1 half bath
Guests 9 guests
Rating 5 (9)
Your Perfect Family Getaway!With spacious rooms, elegant furnishings, and an exceptional outdoor space, 26 Gloucester is the ideal retreat for your next family vacation.The open-concept living area offers plenty of seating, a large wall-mounted Smart TV, and sliding doors that open to an elevated deck. The deck showcases stunning views of the pool,
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 5 bedrooms
Bathrooms 4 full baths
Guests 14 guests
Rating 5 (3)
Take solace in this bright and inviting 3 bedroom, 3 bathroom home located only a short distance to the beach in the lovely Palmetto Dunes Resort on Hilton Head Island. This alluring Palmetto Dunes home is pet-friendly with a private pool and waterfront dock on the Palmetto Dunes lagoon system.This popular waterfront Hilton Head home offers two liv
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (36)
Welcome to Planters Wood 48, a fully renovated 4-bedroom, 4-bathroom luxury home nestled in the highly sought-after Sea Pines community on Hilton Head Island. Designed to comfortably sleep eight guests, this property offers unparalleled convenience, being just minutes away from Harbour Town and the beach. Inside, you'll discover a bright, airy, and
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 4 bedrooms
Bathrooms 4 full baths
Guests 8 guests
Rating 5 (8)
Located in the heart of the highly desired North Forest Beach neighborhood of Hilton Head Island, Lark 2 is a spacious 4-bedroom and 3-bath pet-friendly Forest Beach home that exudes South Carolina Lowcountry beach cottage flare and easy access to Hilton Head’s top beaches and attractions. Just 4 rows from the beach, this stilted Forest Beach vacat
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Featured Properties Special

We’ve handpicked some of our favorite vacation rentals and made them even better with a discount! Browse our featured properties and find the perfect place for your next getaway. Availability is limited, so book your stay today and use promo code FEATURED10 to save today!

Bedrooms 4 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (29)
Nestled in the serene enclave of Sea Pines on Hilton Head Island, Otter Road 105 is your idyllic retreat for a memorable getaway. This charming 3-bedroom, 2-bathroom dog-friendly home exudes warmth and comfort, perfectly accommodating up to six guests. Upon entering, you'll be greeted by a spacious living area designed for relaxation and entertainm
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 6 guests
Rating 5 (4)
The Hilton Head Island vacation of your dreams awaits at this luxurious 3rd row wonder: 2 Capri Lane in North Forest Beach, Hilton Head. This 7 bedroom, 7.5 bathroom Forest Beach home offers glimpses of the ocean, a raised pool and spa deck, spacious interiors for everyone to lounge, contemporary and coastal furnishings. The raised style of the hom
Hot HOT 33
Bedrooms 7 bedrooms
Bathrooms 7 full baths 1 half bath
Guests 22 guests
Rating 5 (25)
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 35
Bedrooms 3 bedrooms
Bathrooms 2 full baths 1 half bath
Guests 8 guests
Rating 5 (9)

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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.