Hilton Head Island Guest Houses

We selected the 94 homes worth renting in this location

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Home spotlights in Hilton Head Island

Fairway Breeze

Fairway Breeze

  • 9 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Spend just a few minutes of lounging on the deck, looking out on the sprawling greens of the Fazio Golf Course, and you'll understand why this Hilton Head home is a must-visit. It's situated in the gated Palmetto Dunes, an oceanfront resort bursting with outdoor activities, including tennis, surf lessons and kayaking in the saltwater lagoon.

Checkered

Checkered

  • 10 guests

  • 5 bedrooms

Cannonborough Elliotborough, Charleston

Spanning two floors, this elegant home embraces its historic setting while offering 21st-century luxuries. Warm and welcoming from the moment you arrive, you'll find a whitewashed living area with contrasting window frames, dining chairs and accent tables.

Lime Green Wish

Lime Green Wish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Neatly tucked away at the back of the lot, this picturesque home offers privacy from the main road. Even as you approach, you’ll be smitten with the Southern characteristics that define it.

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.


We selected the top 3% holiday homes in Hilton Head Island Guest Houses

Explore the 94 most perfect homes in our collection

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Most popular homes in Hilton Head Island

Savannah Serenity

Savannah Serenity

  • 2 guests

  • 1 bedrooms

North Historic District, Savannah

Wicker

Wicker

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Sands & Shimmer

Sands & Shimmer

  • 6 guests

  • 2 bedrooms

Hilton Head Island, Beaufort County

Ain't She Sweet

Ain't She Sweet

  • 16 guests

  • 8 bedrooms

Cannonborough Elliotborough, Charleston

Swing Kings

Swing Kings

  • 8 guests

  • 4 bedrooms

Radcliffeborough, Charleston

Historical Hideout

Historical Hideout

  • 8 guests

  • 4 bedrooms

North Historic District, Savannah

Savannah Serenade

Savannah Serenade

  • 4 guests

  • 1 bedrooms

North Historic District, Savannah

Glory Days

Glory Days

  • 12 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

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Frequently asked questions

Looking for guesthouse style accommodation in Hilton Head Island, Beaufort County, South Carolina, United States? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Hilton Head Island, Beaufort County, South Carolina, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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