Family-friendly holiday rentals in Hilton Head

4.94 out of 5 average rating, 208 reviews

BIKE ‘n BED Hilton Head- 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.

Superhost

Cottage in Hilton Head Island

4.86 out of 5 average rating, 376 reviews

Gypsy Sea Cottage - A Beachside Retreat

Welcome to The Gypsy Sea Cottage—a beautifully renovated stand alone villa nestled in the prestigious Palmetto Dunes Resort, within the serene Queens Grant community. Just a short stroll to pristine beaches, championship golf courses, and world-class dining, this retreat offers a perfect balance of relaxation and adventure. Inside, you'll find high-end furnishings, luxury linens, smart home features, and a well-equipped kitchen—every detail thoughtfully designed for a seamless, memorable stay.

4.95 out of 5 average rating, 255 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!

Townhouse in Hilton Head Island

4.97 out of 5 average rating, 129 reviews

Beachfront Resort Luxury Golf Pickleball Beach Bar

Gated Beachfront Golf Resort! Beach, Golf, Pool, Spa, Restaurants & Bars FREE Tennis & Pickleball – across the street! HGTV Decorator designed Luxe Villa Panoramic Golf & Lagoon Views Big Wraparound Porch Huge Old Oaks dripping in Spanish Moss & Coastal Lagoons! Coastal Décor Sunny 1st Floor KING BED + 2 QUEEN 3 XL SmartTVs FREE: FAST WIFI & HD CABLE Gourmet Kitchen Washer/Dryer Beach Cart, Chairs, Boogie Boards, Ice Chest Gas BBQ Walk/Bike to Beach Walk to Golf Club & Pub Close to Coligny

Flat in Hilton Head Island

4.97 out of 5 average rating, 149 reviews

Fully Renovated 2 Bedroom Villa - Walk to Beach

Make yourself at home in this comfortable 2 story, ground floor Condo. Easy walk to the beach. Open concept living, dining and fully equipped kitchen and 1/2 bath on main floor. Chose either the comfy King or Queen bedroom with walk-in shower or bathtub of your choice. Private courtyard with Grill and outside seating. All this, in a setting of azaleas, palms and 20 steps to pool with stores and restaurants just 2 blocks away. Please note there is only 1 parking space available for your stay.

Superhost

4.77 out of 5 average rating, 137 reviews

Clean Renovated Ground floor Encl Courtyard Bikes

Located in the small, quite, beautifully landscaped St. Andrews Common area of the world class Palmetto Dunes Resort. Located just inside Palmetto Dunes entrance- easy to get to anywhere on the island. Six minute bike ride to beach or Dune buggy picks you up for free. Beach chairs & 2 bikes included. Host is great at communicating with guest and strives to insure you have an excellent vacation. Exceptional cleaning crew keeps condo very clean. Renovated kitchen , bathrooms , flooring.

4.84 out of 5 average rating, 105 reviews

Stunning Ocean & Coastal Views | Resort Perks!

Top-floor 2BR/2BA villa with ocean, marsh & golf views. Enjoy stunning sunrises & sunsets from your balcony. 5-min walk to semi-private beach or take the seasonal shuttle. 1 mile to Shelter Cove's dining, shopping & entertainment. Resort-style community with 3 pools, gym, bike rentals & beach access—perfect for families, couples & girls’ trips! ⭐ Guests Love It! ⭐ ★★★★★ "Kim was SUPER responsive! The view was amazing. The beach was beautiful & uncrowded. My boys & I loved the boardwalk!"

4.88 out of 5 average rating, 168 reviews

Renovated - Walk to Beach - 3 Pools - King Bed!

Renovated top to bottom in 2023! 2 bedrooms, 2 baths, and a full kitchen! Located in the center of Hilton Head Island close to all the wonderful bike trails, restaurants, shopping, and famous golf! In a gated community full of amenities: - Boardwalk to the beach 🏖️ 🌊☀️🐚 - 2 outdoor pools (1 heated) 🤿 - Indoor pool (heated) ☔️ - Hot tub - 6 tennis & 2 pickleball courts 🎾 🏓 - Beachfront bar & grill 🍻 - Poolside bar & grill ⛱️ - Small fitness center 💪🏋️ - Sand Volleyball 🏐

4.98 out of 5 average rating, 261 reviews

Coastal King Beach Flat Convenient to Everything!

Set in a serene location right on the beach, this complex is a peaceful retreat. It is a short walk to Coligny Plaza, a vibrant area with a variety of dining, shopping, and entertainment options. The complex features a pool and sundeck, perfect for relaxation. With high-speed internet, WIFI, smart TVs, Roku, and cable, you're always connected. Enjoy the comforts of home with a fully stocked kitchen, a plush King bed, ideal for remote work, and modern updates & included amenities.

4.95 out of 5 average rating, 337 reviews

1 Minute walk to the beach *Amazing ocean view*

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.

4.91 out of 5 average rating, 139 reviews

HipNautic Couples Beach Escape Indoor Pool Jacuzzi

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.