Hilton Head Island Holiday Homes with Staff

We selected the 88 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

0

Home spotlights in Hilton Head Island

Grand Designs

Grand Designs

  • 14 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

With enough room for families, friends and cartwheels, this large house has an abundance of space. Found on Harbour Town golf course, the home has so many rooms you may get lost – from the games room and downstairs conservatory to the reading nook, living room, and TV space.

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.

Carolina Wren

Carolina Wren

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Arriving at this home is a bit like falling into Charleston’s version of The Secret Garden – a traditional shopfront gives very little indication of the impressive homes that sit behind it. Part of a larger complex, there’s a beautifully landscaped communal garden and terrace for guests to enjoy when the weather is just right.

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.


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

Explore the 88 most perfect homes in our collection

View on map

Most popular homes in Hilton Head Island

Fairway Breeze

Fairway Breeze

  • 9 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

A Stroll in Savannah

A Stroll in Savannah

  • 4 guests

  • 1 bedrooms

North Historic District, Savannah

Lime Green Wish

Lime Green Wish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Salty Breeze

Salty Breeze

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Gateway to Savannah

Gateway to Savannah

  • 2 guests

  • 1 bedrooms

North Historic District, Savannah

Rockfish

Rockfish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Smoke on the Water

Smoke on the Water

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Singing Sweet Carolina

Singing Sweet Carolina

  • 12 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

View all

Check upcoming rates & availability for Hilton Head Island Holiday Homes with Staff


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.

Search Our Collection