Luxury Long Stay Rentals in Hilton Head Island

We selected the 94 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Hilton Head Island

Smoke on the Water

Smoke on the Water

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Amid sandy strands and a network of lagoons, this villa is in one of the most picturesque areas of South Carolina. In just ten minutes, you can move from the water basin's grassy banks to the ocean through the scenic woodland between the two.

Oglethorpe Oasis

Oglethorpe Oasis

  • 4 guests

  • 1 bedrooms

North Historic District, Savannah

A peaceful retreat nestled in the heart of Savannah's North Historic District, between the charming Oglethorpe Square and bustling Broughton Street. Guests will find themselves within walking distance from a plethora of experiences to savour from shopping sprees, savouring delectable cuisine, to immersing oneself in rich history and culture with splendid museums and tourist attractions at every corner.

Swing Kings

Swing Kings

  • 8 guests

  • 4 bedrooms

Radcliffeborough, Charleston

With its white clapboard exterior and powder-blue window shutters, this traditional home is the belle of the ball in Charleston. Step into a Southern scene of four-poster beds, floral wallpaper and palm prints in each of the bedrooms.

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.


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

Rockfish

Rockfish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Dixie Chic

Dixie Chic

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

White Ibis

White Ibis

  • 11 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Singing Sweet Carolina

Singing Sweet Carolina

  • 12 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

Damn Fine Coffee

Damn Fine Coffee

  • 11 guests

  • 5 bedrooms

North Charleston, Charleston County

Island Pines

Island Pines

  • 8 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Savannah Serenity

Savannah Serenity

  • 2 guests

  • 1 bedrooms

North Historic District, Savannah

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. 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 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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