Hilton Head Island Holiday Homes with Staff

We selected the 90 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

Salty Breeze

Salty Breeze

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

In between Harbour Town and South Beach on Hilton Head Island, this home epitomises holiday living with beach vibes abound thanks to the spot's whiteboard walls and maritime-themed furnishings. We particularly love the generous amount of social space; there's a double-volume living room and myriad of areas for guests to gather.

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.

Dixie Chic

Dixie Chic

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Welcome to small but charming Charleston, once again topping Condé Nast Traveler's Readers' Choice Awards. Whether you’re here to explore its colonial architecture, tuck into excellent Creole and BBQ food or savour the blossoming cocktail scene, you’re going to need somewhere to stay smack bang in the heart of the buzz.


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

Explore the 90 most perfect homes in our collection

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Most popular homes in Hilton Head Island

Fairway Breeze

Fairway Breeze

  • 9 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Cameo Pink

Cameo Pink

  • 6 guests

  • 3 bedrooms

Park Circle, North Charleston

Rocking Chair Residence

Rocking Chair Residence

  • 20 guests

  • 10 bedrooms

Cannonborough Elliotborough, Charleston

Island Pines

Island Pines

  • 8 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Carolina Wren

Carolina Wren

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Summer Duck

Summer Duck

  • 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

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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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