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

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.

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.

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.

Ain't She Sweet

Ain't She Sweet

  • 16 guests

  • 8 bedrooms

Cannonborough Elliotborough, Charleston

It can sometimes be difficult to find a home for a big group getaway – the balance between communal spaces and private corners is always a tricky one, but this home definitely gets it right. Or perhaps we should say homes, as you'll find yourselves spread across two separate buildings, with a shared garden and courtyard between them.


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

Explore the 94 most perfect homes in our collection

View on map

Most popular homes in Hilton Head Island

Smoke on the Water

Smoke on the Water

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Charming Savannah Retreat

Charming Savannah Retreat

  • 8 guests

  • 3 bedrooms

North Historic District, Savannah

Salty Breeze

Salty Breeze

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Summer Heat

Summer Heat

  • 6 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Rockfish

Rockfish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Summer Duck

Summer Duck

  • 8 guests

  • 4 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

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