Hilton Head Island Holiday Homes with Staff

We selected the 96 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

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Home spotlights in Hilton Head Island

Glory Days

Glory Days

  • 12 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

Time to polish off the ring and get down on one knee because this home has us head over heels. Only two hundred metres from the beach, this Hilton Head Island villa is a luxurious, private hideaway made for lazy summer days.

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.

Cotillion

Cotillion

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

This home may look traditional on the outside, but inside it's very much shaking things up. Slow Southern days unwind on the pastel painted veranda, with its rocking chairs and swing – the perfect spot to get lost in a good book or natter with the rest of your group over an iced tea.

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 96 most perfect homes in our collection

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Most popular homes in Hilton Head Island

Among The Dunes

Among The Dunes

  • 15 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

Charming Savannah Retreat

Charming Savannah Retreat

  • 8 guests

  • 3 bedrooms

North Historic District, Savannah

Island Pines

Island Pines

  • 8 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Wicker

Wicker

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Hominy

Hominy

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Dixie Chic

Dixie Chic

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

White Ibis

White Ibis

  • 11 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Smoke on the Water

Smoke on the Water

  • 12 guests

  • 4 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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