Hilton Head Island Holiday Homes with Staff

We selected the 94 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

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.

Wicker

Wicker

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Surrounded by lagoons on all sides, this low-country home is tucked into the flora and fauna of Hilton Head Island. The gracious nature of the home makes it ideal for both a short summer weekend and long stay alike.

Square Dance

Square Dance

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Located just outside of Charleston's historic downtown area and close to the shops, restaurants and bars of King Street, this home is in an enviable position within the city. And just like its surroundings, the building itself is steeped in history.

Southern Charm

Southern Charm

  • 10 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Embracing past and present, as all Charleston homes should, a careful balance of contemporary southern living with traditional features gives this home an elegant feel. Featuring beautiful hardwood floors, exposed beams and customary shutters, you’ll feel grounded in this historic location.


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

Explore the 94 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

Riverfront Retreat

Riverfront Retreat

  • 6 guests

  • 2 bedrooms

North Historic District, Savannah

Island Pines

Island Pines

  • 8 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Glory Days

Glory Days

  • 12 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

Cotillion

Cotillion

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Carolina Wren

Carolina Wren

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Smoke on the Water

Smoke on the Water

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

White Ibis

White Ibis

  • 11 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

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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.

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