Hilton Head Island Holiday Homes with Staff

We selected the 86 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Hilton Head Island

Island Pines

Island Pines

  • 8 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

There is a certain kind of charm only found in the South, and this house has it in spades. Beautifully situated on the grounds of a vast private estate, surrounded by golf courses, and resting in the shadow of a stunning forest, this is an ideal spot for a restful and luxurious retreat for a family or a group of friends.

Oystercatcher

Oystercatcher

  • 6 guests

  • 2 bedrooms

Hilton Head Island, Beaufort County

There’s a real sense of calm about this newly remodelled beach house. Whether it’s the neutral shades, or the copious amounts of natural light, you’ll find any tension melting away the minute you step through the door.

Hominy

Hominy

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Just behind Upper King Street, this home benefits from a great location and plenty of peace and quiet. Part of a larger complex of homes, there is a lovely shared garden for residents to use, and with plenty of ancient trees, you won’t be running out of shady corners either.

Rockfish

Rockfish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Located on the second floor of a restored wood-fronted home in the heart of Charleston’s Cannonborough-Elliotborough neighbourhood, this home boasts an enviable position and charming interiors. Exposed trusses add an element of drama to the whitewashed living area and, thanks to its open concept, it’s also a lovely space in which to relax and spend quality time as a group.


We selected the top 3% holiday homes in Hilton Head Island Holiday Homes with Staff

Explore the 86 most perfect homes in our collection

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Most popular homes in Hilton Head Island

Oyster & Pearl

Oyster & Pearl

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Savannah Serenade

Savannah Serenade

  • 4 guests

  • 1 bedrooms

North Historic District, Savannah

Damn Fine Coffee

Damn Fine Coffee

  • 11 guests

  • 5 bedrooms

North Charleston, Charleston County

Salty Breeze

Salty Breeze

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Southern Charm

Southern Charm

  • 10 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Checkered

Checkered

  • 10 guests

  • 5 bedrooms

Cannonborough Elliotborough, Charleston

Fairway Breeze

Fairway Breeze

  • 9 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Singing Sweet Carolina

Singing Sweet Carolina

  • 12 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

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Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Hilton Head Island, Beaufort County, South Carolina, United States? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in Hilton Head Island, Beaufort County, South Carolina, United States as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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