Family-friendly holiday rentals in Hilton Head Island

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Top-rated family-friendly rentals in Hilton Head Island

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Guest favourite

Apartment in Hilton Head Island

4.93 out of 5 average rating, 166 reviews

Hilton Head BIKE 'n BED - Perfect Couple's Getaway

Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

28 Dec – 4 Jan

$162 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.96 out of 5 average rating, 211 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your private balcony. Private beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!

29 Oct – 5 Nov

$225 SGD per night

Superhost

Apartment in Hilton Head Island

4.84 out of 5 average rating, 267 reviews

Gorgeous villa, private beach access, HH Resort

Top floor, beautiful 2 bedrm beach villa with stainless appliances, and a private terrace in an Oceanside gated Resort community awaits you. Our beautiful beach condo with private beach access is just a short walk over our picturesque boardwalk. Shelter Cove shops & restaurants are nearby, and Krogers Supermarket & Whole Foods are 5 min away. We are next door to Palmetto Dunes & Robert Trent Championship Golf Course. Perfect mid island location. Great for couples, families & solo adventurers!

21–28 Nov

$238 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.91 out of 5 average rating, 169 reviews

2Bd/2.5 bth/Near Coligny Park/Few Blocks To Beach

Located within a short walking distance to the white beaches of Hilton Head, this beautiful vacation rental which sleeps up to 6 guests is ready to become your home away from home while you explore everything that the island has to offer. A relaxing beach getaway in this spacious second level townhome that boasts a fully equipped kitchen and two master suites and is within an easy walk/bike ride to the famous Coligny Circle shops and restaurants. Free hour at the Van der Meer Tennis Center.

30 Jan – 6 Feb

$240 SGD per night

Guest favourite

Flat in Bluffton

4.96 out of 5 average rating, 546 reviews

Bluffton Villa in the heart of the Promenade

Beautiful villa in the heart of the Promenade in the Historic District of Bluffton. Steps away are a wine bar, coffee shop, French bakery, 5 star and casual dining, & fabulous boutique shopping. Newly built in 2017, we offer our guests a fully equipped kitchen with an electric convection oven, microwave, dishwasher, ice maker in refrigerator. The bathroom offers a large walk in shower with a rain shower head, and the bedroom has a King size bed. You are a 15 minute ride to Hilton Head.

3–10 Oct

$220 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.91 out of 5 average rating, 281 reviews

Turtle Tracks, Hilton Head Island, SC

Walk to the BEACH! This newly remodeled 2 bedroom/2 bathroom villa is located in a gated community with 24 hour security & private access to one of the most beautiful beaches in HHI! Our condo, located in Building 1, is the closest building to the beach. Walk 400 yards via our boardwalk, over the marsh to a beautiful, uncrowded beach!. Included are tennis courts, 2 outdoor pools/1 indoor, 1 hot tub, track & weight room. Free WIfi. No pets or emotional support animals are allowed per HOA.

23–30 Nov

$181 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.86 out of 5 average rating, 234 reviews

Shore To Please! Elegant couples retreat w/bikes

Stylish beach retreat: Enjoy ocean views and comfortable, Scandinavian design from this newly renovated villa located steps from the beach and within walking distance to many shops, restaurants & entertainment. This well-appointed villa features a beautiful, stocked kitchen, new flooring, walk-in shower and separate bedroom with a desk perfect for getting a little work done. Enjoy ocean-view dining on the balcony or at the kitchen island. There are beach chairs and 2 bikes for your use.

20–27 Nov

$204 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 222 reviews

Clean/Updated King on the Beach Walk to Everything

Great location on the beach! Walking distance to Coligny Plaza where there are a multitude of restaurants, cafe's, cute shops, bike rental places everything you need. FREE high speed internet WIFI, smart tvs, Roku. All of the comforts of home including fully stocked kitchen, comfortable King bed, great layout for remote working. Many extra amenities including beach chairs, umbrellas, water/soft drinks, 6 Coffee K-cups, cooler, first aid kit, Iron, luggage rack, and more.

15–22 Mar

$282 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.94 out of 5 average rating, 283 reviews

*Amazing ocean view villa* Bikes included.

Enjoy Amazing ocean and beach views from your balcony. This is the 3rd unit from the ocean on the 3rd floor and honestly the view beats the direct oceanfront views because of the panoramic effect. Sea Side Villas is minutes away from the very popular Coligny Beach Park area where you can enjoy the many restaurants and shops. Also very close to the new Lowcountry Celebration Park where they have festivals and events.

15–22 Oct

$501 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.93 out of 5 average rating, 115 reviews

Hip Nautic Couples Beach Condo, Pickleball/Hot Tub

Embrace the relaxed coastal lifestyle at Hip Nautic, a short stroll from the beach. Our cozy one-bedroom condo provides the essential comforts for travelers seeking a convenient retreat. Located just three blocks away from shopping, dining, and year-round live music, our prime spot offers the perfect gateway to explore Hilton Head Island, renowned as the 2017 “Top Island in the U.S." by Conde Nast Traveler.

2–9 Dec

$198 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.85 out of 5 average rating, 234 reviews

Charming Sea Pines Villa with View on Hilton Head

New Appliances!! Enjoy this lovely condo with gorgeous views overlooking Braddock Cove. Top floor 1 BR villa located in SeaPines at South Beach. A short walknext door to Salty Dog Cafe/South Beach Marina with restaurants and shopping. It's also a barefoot walk across the way from beautiful Calibogue Sound (beach) for incredible dolphin/sunset watching!

14–21 Mar

$199 SGD per night

Guest favourite

Guest house in Bluffton

4.98 out of 5 average rating, 355 reviews

Hickory Trace Carriage House

In the heart of Historic Bluffton, walking distance to restaurants, galleries, shops & the beautiful May River. Built in 2015 featuring an open floor plan, fully equipped kitchen, washer & dryer, queen bed & sofa bed. Full of lovely Southern Charm! http://www.onlyinyourstate.com/maryland/little-known-restaurants-md/

11–18 Nov

$182 SGD per night