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, 167 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.

Guest favourite

Apartment in Hilton Head Island

4.96 out of 5 average rating, 212 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!

Guest favourite

Townhouse in Hilton Head Island

4.98 out of 5 average rating, 107 reviews

Beachfront Resort! Designer 2/2 Lagoon + Golf View

Gated Beachfront Golf Resort! HGTV Featured Decorator designed Luxe Villa Panoramic Lagoon & Golf View from huge Patio! Beach, Golf, Tennis, Pickleball, Pool, Spa, Restaurants & Bars Huge Old Oaks dripping in Spanish Moss & Coastal Lagoons! Stylish Coastal Décor Sunny 1st Floor KING BED + 2 QUEENs 3 SmartTVs FREE: WIFI, CABLE, NETFLIX & PRIME Gourmet Kitchen Washer/Dryer Beach Cart, Chairs, Umbrella, Boogie Boards, Ice Chest Gas BBQ Walk to Golf Club & Pub Walk/Bike to Beach Close to Coligny

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.

Guest favourite

Apartment in Hilton Head Island

4.83 out of 5 average rating, 142 reviews

Beach condo: Heated POOL! 2 bathrooms

COME STAY at this charming beach-walk community! The pool is at the bottom of the stairs, 5 minute walk to the beach, & only 3/4 of a mile to Coligny circle with grocery store, shops, and restaurants. “COPPERTONE DAYS” features: 4 twin beds(memory foam), a master bedroom/master bath, laundry room, and a stocked kitchen+ highchair and a crib! It has a Fresh southern style with finds from island boutiques and Pottery Barn. We can usually accommodate early arrivals. Just reach out!

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 224 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.

Guest favourite

Apartment in Hilton Head Island

4.94 out of 5 average rating, 287 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.

Guest favourite

Apartment in Hilton Head Island

4.93 out of 5 average rating, 117 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.

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!

Guest favourite

Guest house in Tybee Island

4.93 out of 5 average rating, 380 reviews

Sunny Daze Tiny Cottage

This adorable tiny cottage is a perfect get-away for a couple or solo-traveler. This sweet little guesthouse features a full-sized bed, kitchenette, bathroom/shower as well as a fenced-in backyard with a large relaxing pond in the front yard. The home is just a 5-minute walk to the beach and a short walk to restaurants & pubs!

Guest favourite

Guest house in Bluffton

4.98 out of 5 average rating, 358 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/

Guest favourite

Apartment in Hilton Head Island

4.88 out of 5 average rating, 138 reviews

Book Now! 115A King bed/Indoor pool/pickleball

1BD/1BA condo on first floor (no stairs to climb or elevator) close to Coligny Plaza and the beach. Bathroom renovated in May 2022. Outdoor and indoor pools on the property and Jacuzzi . Keurig provided. This is the A unit of a lockout unit. There may be guests in the B unit during your stay.