Charleston Holiday Homes with Staff

We selected the 92 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 Charleston

The Lindy Hop

The Lindy Hop

  • 6 guests

  • 3 bedrooms

Charleston County, South Carolina

Between the wildlife-filled waterways and historic plantation homes of James Island, this rustic Charleston hideaway offers intimacy and seclusion. Its bright, minimalist interiors reflect the gentle rhythm of southern life, with hardwood floors harking back to days of tradition.

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.

Leafy & Peach

Leafy & Peach

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Southern family living meets beach charm at this home on Hilton Head Island. The wraparound porch, pool and ping-pong table make it the perfect place to while away long afternoons in the sun.

Sands & Shimmer

Sands & Shimmer

  • 6 guests

  • 2 bedrooms

Hilton Head Island, Beaufort County

You’ll breathe a sigh of contentment the minute you step through the door of this dreamy beachfront apartment. Beautifully finished in natural sand and earth tones, this home feels like a continuation of the rolling dunes just beyond the balcony.


We selected the top 3% holiday homes in Charleston Holiday Homes with Staff

Explore the 92 most perfect homes in our collection

View on map

Most popular homes in Charleston

Swing Kings

Swing Kings

  • 8 guests

  • 4 bedrooms

Radcliffeborough, Charleston

Riverfront Retreat

Riverfront Retreat

  • 6 guests

  • 2 bedrooms

North Historic District, Savannah

River Reach

River Reach

  • 7 guests

  • 3 bedrooms

Folly Beach, Charleston County

Summer Duck

Summer Duck

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Glory Days

Glory Days

  • 12 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

White Ibis

White Ibis

  • 11 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Square Dance

Square Dance

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Rocking Chair Residence

Rocking Chair Residence

  • 20 guests

  • 10 bedrooms

Cannonborough Elliotborough, Charleston

View all

Check upcoming rates & availability for Charleston Holiday Homes with Staff


Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Charleston, Charleston 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 Charleston, Charleston 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