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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!

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Displaying 1 - 63 of 63 results matching your search criteria
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32 Corine Lane

Vacation Homes of Hilton Head
6 Bedrooms
6 Baths

This beautifully decorated 6 bedroom, 6 bath open concept home has three master bedroom suites with king beds and flat screen TVs.

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3 Sutherland Court

Vacation Homes of Hilton Head
6 Bedrooms
4 Baths

This updated 6 bedroom house is located in the prestigious private community of Palmetto Dunes and is just a hop skip and a jump away from the beach!

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13 Moonshell Road

Vacation Homes of Hilton Head
4 Bedrooms
3 Baths

13 Moonshell Road is the perfect low-country home for your visit to Hilton Head. With 4 bedrooms, 3 bathrooms, a huge fence in back yard with private pool and outdoor bar, this house is perfect for slowing down and enjoying time with loved ones.

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4 Sandy Beach Trail

Vacation Homes of Hilton Head
6 Bedrooms
6.5 Baths

This third row, 6 bedroom/6.5 bathroom pet friendly home features a spacious deck and private pool! This home is located in beautiful Burke's Beach and is just a three minute walk to the beach!

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1 Sandy Beach Trail

Vacation Homes of Hilton Head
6 Bedrooms
5.5 Baths

1 Sandy Beach Trail is a captivating 6 bedroom, 5 1/2 bathroom home with a large private pool, just one short block to the beach.

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27 Singleton Beach Place

Vacation Homes of Hilton Head
6 Bedrooms
7 Baths

This direct oceanfront home sleeps 18 and is sure to please with its open concept floor plan and stunning 360 degree views of the ocean & beautiful marsh.

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14 Collier Beach Road

Vacation Homes of Hilton Head
6 Bedrooms
6 Baths

This gorgeous oceanfront estate was fully renovated in Winter 2020. The home boasts a gorgeous master suite with amazing views of the Atlantic Ocean, marble bathroom, and free form tub.

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21 Singleton Beach Place

Vacation Homes of Hilton Head
6 Bedrooms
7.5 Baths

This 6-bedroom 7.5-bathroom extravagant home is newly constructed (just built in 2016) with amazing oceanfront views, open concept floor plan, and top of the line décor and appliances.

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12 Collier Beach Road

Vacation Homes of Hilton Head
6 Bedrooms
5.5 Baths

This beautiful oceanfront dream is located midisland in the Singleton Beach community conveniently located near tons of local shops, restaurants, and attractions. Vacationers are sure to enjoy this comfy well-equipped home will make for a perfect vacation!

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10 Collier Beach Road

Vacation Homes of Hilton Head
6 Bedrooms
7.5 Baths

This beautiful 6-bedroom oceanfront home will make for the most perfect private getaway offering amazing ocean views, private pool, private beach access, a chef's kitchen and more. Call us for more details...

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27 Corine Lane

Vacation Homes of Hilton Head
7 Bedrooms
7 Baths

27 Corine Lane is a luxury 3-story home located in beautiful Singleton Beach. It features a private pool and elevator and boasts 7-bedrooms and 7 bathrooms.

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133 Dune Lane

Vacation Homes of Hilton Head
4 Bedrooms
4 Baths

This 4-bedroom 4 bath oceanfront home offers the best in casual beach living.All four bedrooms have unobstructed views of the ocean, and bathrooms are spacious and comfortable. This beach bungalow has it all!

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10 Gardenia Street

Vacation Homes of Hilton Head
4 Bedrooms
2.5 Baths

Beautifully renovated 4 bedroom range in the highly coveted community of Folly Field. This coastal chic beach cottage will make all of your vacation dreams come true.

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19 Sand Dollar Road

Vacation Homes of Hilton Head
5 Bedrooms
5.5 Baths

This second-row ocean home blends traditional coastal Carolina styling with charming high-end details that guarantee a memorable beach vacation!

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18 Sand Dollar Road

Vacation Homes of Hilton Head
7 Bedrooms
7 Baths

18 Sand Dollar is sure to impress the entire group offering 7 bedrooms, 7 bathrooms, an open concept floor plan and over-sized chef’s kitchen! This home also features a pool table with ping pong & Foosball table on the second floor!

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