Family-friendly vacation rentals in Hilton Head Island

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Top-rated family-friendly rentals in Hilton Head Island

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Guest favorite

Condo in Hilton Head Island

4.93 out of 5 average rating, 165 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.

Mar 11 – 18

ﺩ.ﺇ622 per night

Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 209 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!

Apr 19 – 26

ﺩ.ﺇ725 per night

Guest favorite

Condo in Hilton Head Island

4.8 out of 5 average rating, 127 reviews

After Dune Delight Beach Condo, Pickleball/Hot Tub

Experience the effortless charm of coastal living at After Dune Delight, where every moment feels like a breeze. Nestled just a short 10 min walk from the sandy shores, our inviting one-bedroom condo offers a retreat that feels just like home, only better. Indulge in the spacious comfort of our accommodations, thoughtfully equipped with all the essentials for a relaxing stay. From cozy furnishings to convenient amenities, we've curated an experience that seamlessly blends comfort and luxury.

Nov 14 – 21

ﺩ.ﺇ569 per night

Guest favorite

Condo in Hilton Head Island

4.91 out of 5 average rating, 168 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.

Apr 14 – 21

ﺩ.ﺇ652 per night

Guest favorite

Apartment 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.

Oct 12 – 19

ﺩ.ﺇ599 per night

Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 221 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.

Apr 18 – 25

ﺩ.ﺇ862 per night

Guest favorite

Condo in Hilton Head Island

4.95 out of 5 average rating, 130 reviews

Gorgeous beach villa 2BD/2BA at Hilton Head Resort

Our beautiful beach with private access is open! Gorgeous & updated 2BD/2BA beach villa at Hilton Head Resort! New kitchen, newer baths ~perfect & relaxing for your island getaway! This Oceanside condo complex is just a short walk to the beach over our picturesque private boardwalk. Shelter Cove shops, marina and restaurants nearby. Kroger supermarket and Whole Foods 5 min away. Perfect mid island location and great for families & couples - everyone is welcome!

Dec 4 – 11

ﺩ.ﺇ630 per night

Guest favorite

Condo in Hilton Head Island

4.94 out of 5 average rating, 281 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.

Sep 24 – Oct 1

ﺩ.ﺇ1,375 per night

Superhost

Cottage in Hilton Head Island

4.86 out of 5 average rating, 301 reviews

Gypsy Sea Cottage - A Seaside Retreat

Our place is located in prestigious Palmetto Dunes in a stand alone unit inside the Queens Grant Villas with easy access to beautiful beaches, world class golf, and great food. Newly remodeled The Gypsy Sea Cottage boasts high end furnishings, quality linens, high tech amenities, a fully stocked kitchen, and the attention to detail that makes for an unforgettable vacation.

Dec 6 – 13

ﺩ.ﺇ653 per night

Guest favorite

Condo 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!

Nov 28 – Dec 5

ﺩ.ﺇ540 per night

Guest favorite

Condo in Hilton Head Island

4.81 out of 5 average rating, 143 reviews

SeaForever-King Bed, Ocean Views w/ Beach Access

Enjoy ocean views from the balcony of this first floor villa in the heart of Hilton Head's main beach! The villa features a full kitchen, king bed in the bedroom, and a sleeper sofa in the living room. Flat screen TV's in both the bedroom and living room and WiFi. Just steps to the beach or pool, every thing needed for your beach vacation!

Dec 19 – 26

ﺩ.ﺇ451 per night

Guest favorite

Guesthouse 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/

Sep 28 – Oct 5

ﺩ.ﺇ495 per night