Book Family Friendly Rentals in Hilton Head Island

We selected the 42 homes worth renting in this location

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Home spotlights in Hilton Head Island

Cameo Pink

Cameo Pink

  • 6 guests

  • 3 bedrooms

Park Circle, North Charleston

With ample space and chic, comfortable furniture, Cameo Pink is a practical and stylish option for a getaway with family or friends – and if you’re travelling with a bigger group, you can also rent the house next door. The flowing, open layout and great natural light make it a lovely place to spend time in day and night, and the rocking chairs on the porch are perfect for chatting as the sun sets or just relaxing with a book.

Dixie Chic

Dixie Chic

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Welcome to small but charming Charleston, once again topping Condé Nast Traveler's Readers' Choice Awards. Whether you’re here to explore its colonial architecture, tuck into excellent Creole and BBQ food or savour the blossoming cocktail scene, you’re going to need somewhere to stay smack bang in the heart of the buzz.

Oyster & Pearl

Oyster & Pearl

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Part of Sea Pines Plantation, where it all started for holiday rentals on beautiful Hilton Head Island, this fully renovated home is the perfect place to switch off and relax. Just a short walk from the beach, and with all the gated community's excellent amenities on hand, it's a peaceful and private getaway surrounded by pretty gardens and mature trees.

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.


We selected the top 3% holiday homes in Hilton Head Island Family Friendly Rentals

Explore the 42 most perfect homes in our collection

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Most popular homes in Hilton Head Island

Swing Kings

Swing Kings

  • 8 guests

  • 4 bedrooms

Radcliffeborough, Charleston

Damn Fine Coffee

Damn Fine Coffee

  • 11 guests

  • 5 bedrooms

North Charleston, Charleston County

The Lindy Hop

The Lindy Hop

  • 6 guests

  • 3 bedrooms

Charleston County, South Carolina

Hominy

Hominy

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

Woodpecker's Island

Woodpecker's Island

  • 6 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Fairway Breeze

Fairway Breeze

  • 9 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Ain't She Sweet

Ain't She Sweet

  • 16 guests

  • 8 bedrooms

Cannonborough Elliotborough, Charleston

Lime Green Wish

Lime Green Wish

  • 8 guests

  • 4 bedrooms

Cannonborough Elliotborough, Charleston

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Check upcoming rates & availability for Hilton Head Island Family Friendly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Hilton Head Island, Beaufort County, South Carolina, United States. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Hilton Head Island Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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