Luxury Long Stay Rentals in Hilton Head Island

We selected the 94 homes worth renting in this location

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Home spotlights in Hilton Head Island

Among The Dunes

Among The Dunes

  • 15 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

We’ve got to hand it to this gorgeous home — or should we say mansion — on Hilton Head Island. As far as luxurious hideaways go, this one exudes class.

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.

Island Pines

Island Pines

  • 8 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

There is a certain kind of charm only found in the South, and this house has it in spades. Beautifully situated on the grounds of a vast private estate, surrounded by golf courses, and resting in the shadow of a stunning forest, this is an ideal spot for a restful and luxurious retreat for a family or a group of friends.

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.


We selected the top 3% holiday homes in Hilton Head Island Long Stay Rentals

Explore the 94 most perfect homes in our collection

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Most popular homes in Hilton Head Island

Cotillion

Cotillion

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Dixie Chic

Dixie Chic

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Singing Sweet Carolina

Singing Sweet Carolina

  • 12 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

Double Trouble

Double Trouble

  • 15 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

Suburban Haven

Suburban Haven

  • 5 guests

  • 2 bedrooms

North Charleston, Charleston County

Grand Designs

Grand Designs

  • 14 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

Rockfish

Rockfish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Hominy

Hominy

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

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Check upcoming rates & availability for Hilton Head Island Long Stay Rentals


Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Hilton Head Island, Beaufort County, South Carolina, United States. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Hilton Head Island, Beaufort County, South Carolina, United States collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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