Family-friendly holiday rentals in Hilton Head Island

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Hilton Head Island

Total holiday rentals
Explore 5,170 holiday rentals in Hilton Head Island
Nightly prices starting at
Hilton Head Island holiday rentals start at £30 per night before taxes and fees
Verified guest reviews
Over 97,000 verified reviews to help you choose
Pet-friendly holiday rentals
Find 930 rentals that welcome pets
Holiday rentals with a pool
4,310 properties feature pools
Rentals with dedicated workspaces
2,540 properties have a dedicated workspace
Wifi availability
5,150 of Hilton Head Island holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Hilton Head Island rentals
4.8 Average rating
Hilton Head Island stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated family-friendly rentals in Hilton Head Island

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite

A candle is displayed on a table, surrounded by seashells, with a sunset view of the ocean in the background. The warm colors of the sky reflect off the water, while a cup is placed nearby, adding to the serene atmosphere of the balcony.

Apartment in Hilton Head Island

4.99 out of 5 average rating, 131 reviews

Ocean View KING BED 75"TV Beach Bar Pickleball GYM

✨Top Airbnb Guest Favorite Home✨ Ocean Views from Living Room & Balcony Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar FREE Pickleball, Tennis, Gym & More KING BED + 75" & 65" Smart TVs Expanded Bedroom HGTV Featured Decorator 100% NEW Luxury renovation Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley Stop

Top guest favourite

Apartment in Hilton Head Island

4.95 out of 5 average rating, 131 reviews

Big OceanView 65TV Beach Bar Pickleball Tennis Gym

✨ Top Airbnb Guest Favorite ✨ Big Ocean View from Living Room & Balcony! Oceanfront Building Steps to Beach, Pool, Tiki Bar & Grill FREE: Pickleball, Tennis, Gym, Volleyball Queen Bed | Queen Sofa | 2 Bunks Beach Chairs, Boogie Boards & More! 65" SmartTV Fast WiFi 652 mbps HGTV Decorator Updated Top Floor w/Elevator Couples/Small Families RESORT: Oceanfront Pool, Bar & Grill 4 Beach Boardwalks Sports Bar w/Pool Table Bike Rentals Big Shady Playground 2nd pool 3 BBQ Areas Gated 24/7 Security

Top guest favourite

The image captures a sandy beach at sunset, with gentle waves lapping at the shore. Tall grass frames the scene, and the sun casts a warm glow over the water. Silhouettes of individuals can be seen in the distance, enjoying the serene ambiance.

Apartment in Hilton Head Island

4.97 out of 5 average rating, 307 reviews

Ocean View! Remodeled! Steps to beach/Pool/Bar

FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!

Top guest favourite

A welcoming living area is presented, featuring a comfortable sofa and a round dining table with two chairs. A wall-mounted television is visible. Natural light floods in through sliding glass doors, offering a view of palm trees and outdoor seating.

Apartment in Hilton Head Island

5 out of 5 average rating, 100 reviews

The Lookout - A Modern Beach Retreat (Oceanfront)

Welcome to The Lookout! The moment you step into this villa you will be greeted by an open floor plan, a fully stocked kitchen, & every amenity that you'll need for your stay. Take a seat on one of the high top adirondack chairs & enjoy your favorite beverage while overlooking the most popular beaches on the island. Truly - every square inch of this unit has been meticulously utilized to give you an unforgettable vacation. We look forward to hosting you at Seaside Villa's premier luxury villa!

Top guest favourite

The image captures a private heated pool beneath a covered patio. Comfortable lounge chairs surround the pool, and an outdoor dining area features a large table with chairs. A shaded umbrella stands above the table, while greenery and a grill are visible, enhancing the outdoor setting.

Home in Hilton Head Island

5 out of 5 average rating, 119 reviews

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

Guest favourite

An outdoor area features a heated private pool surrounded by a spacious patio and lounge chairs. The home, with updated siding, has a shaded seating area and a barbecue grill. Lush greenery and colorful flowers enhance the tranquil ambiance.

Home in Palmetto Dunes

4.85 out of 5 average rating, 117 reviews

Palmetto Dunes House: Private Pool, PDBeach, Golf

Magnolia & Maple is your upgraded resort destination. Sat to Sat rentals. Home includes a desk with hi-speed internet, surround sound in the living room and updated décor. This 3 BR, 2 BA home sits on a quite street and offers the opportunity to relax by the private heated pool, walk/bike the 3/4 of a mile to PD's famous beaches, or get some exercise with tennis, golf, or pickleball. Close to Shelter Cove shopping and dining. HHI is a pedestrian and bike friendly area with plenty to do.

Top guest favourite

A serene beach scene features a boardwalk leading to the water, surrounded by soft sand and lush greenery. The sky is expansive, showcasing soft clouds merging with blue hues. The shoreline is visible in the distance, offering a peaceful atmosphere.

Apartment in Hilton Head Island

4.99 out of 5 average rating, 142 reviews

Beach condo with pool and stunning nature views

Warm, modern, and designed with character—this newly remodeled 2-bed/2-bath is the closest condo to Hilton Head's hidden gem beach, with lagoon and sound views. King bed in the primary, twin beds in the kids' room: screened-in sunroom, 3 pools, hot tub, tennis. Fully stocked kitchen with a guest-favorite coffee bar, restocked fresh each stay. In-unit laundry, big-screen TVs in every room, all the beach gear you need (cart, chairs, boards, toys, and more), 400 MB Internet—no cleaning fee!

Top guest favourite

A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.

Apartment in Hilton Head Island

4.96 out of 5 average rating, 218 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, DIRECT, OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! KING BED! CAN SLEEP 4! THIS IS LUXURY LIVING WITH NO RESORT AMENITY CHARGES! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER NAMED RESORTS LUXURY HOTEL PROPERTIES! **UPGRADED INTERNET & HD TV PACKAGE + FREE AMENITIES**

Top guest favourite

The kitchen features white cabinetry with glass accents and a spacious granite countertop. A stainless steel sink is positioned near the window, while a variety of wine bottles and a tray of cookies are arranged on the countertop, adding functionality and a touch of comfort.

Townhouse in Shipyard

4.98 out of 5 average rating, 289 reviews

Hilton Head Villa With Golf View, Stroll to beach

Proudly selected by HGTV as one of nine “Wow Worthy Vacation Homes and Design on HHI”, alongside the 2020 HGTV Dream Home. This upscale home offers seamless in/outdoor living and a generous granite kitchen. During your stay, enjoy the comforts of home - from the plush sectional sofa and Smart TV's, to the hotel-like King bed and en suite bathroom in the master suite. Enjoy the indoor/ outdoor living of your own private villa in the exclusive Greens community of Shipyard Plantation.

Top guest favourite

A bright and inviting living space features a gray sofa with decorative pillows and a white coffee table on a patterned rug. The modern kitchen showcases white cabinetry and a dining area with stools. Fresh flowers are arranged in a vase on the table.

Apartment in Hilton Head Island

4.99 out of 5 average rating, 440 reviews

Ocean Front Resort Condo

Enjoy Coastal Cottage Living in a lovely 540 sq ft one bedroom vacation villa within the activity-filled gated resort of Hilton Head Beach and Tennis. Completely remodeled from with all new fixtures, furnishings, housewares and accessories, this charming beach villa has just opened its doors for guests in March 2019. Amenities include coffee, popcorn, breakfast treats and bottled water to consume; and beach towels, chairs, umbrellas and other items to borrow while here.

Top guest favourite

Apartment in Sea Pines

5 out of 5 average rating, 121 reviews

5 Star Location-Harbourtown-Walkable Area

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Superhost

A spacious outdoor pool area is surrounded by palm trees and lounge chairs, with direct views of the ocean in the background. Clear blue skies and well-maintained landscaping contribute to a refreshing, open atmosphere.

Apartment in Hilton Head Island

4.9 out of 5 average rating, 234 reviews

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

Welcome to the Island! Relax and enjoy our direct oceanfront, pool front, one bedroom, one bathroom, beautiful beach villa. Look out your balcony and see nothing but ocean water! Listen to the waves on your spacious, private balcony, while soaking up the sun during the day or relaxing & star gazing at night. You will enjoy the wonderful accommodations and convenient location very close to the popular Coligny Plaza with spectacular views at Ocean Dunes!