Family-friendly holiday rentals in Hilton Head Island

4.97 out of 5 average rating, 347 reviews

Ocean/Marsh View KING BED Beach Bar GYM Pickleball

✨Top Guest Favorite Home✨ Beachfront Building! Steps to Beach, Pool, Tiki Bar & Grille! Quiet Top Floor: Marsh & Ocean Views KING BED + 2 XL SmartTVs FREE Pickleball, Tennis, Gym + More HGTV Decorator FAST WiFi (574 mbps) Couples Retreat Beach Chairs, Boogie Boards, Ice Chest+More 🏝️RESORT🏝️ 4 Private Beach Boardwalks Huge Oceanfront Pool Beachfront Tiki Bar & Grille Sports Bar & Grille 2nd Pool Bike Rentals in Resort Gated 24 HR Security HUGE shady Playground FREE Island Trolly (April-Sept)

4.95 out of 5 average rating, 105 reviews

Steps to Beach, Pool, 5BR, Great Location

Make this brand new (2023) custom built home, Sur La Mer at Burkes Beach, your vacation destination! This 5 bedroom home is a guaranteed picture perfect destination for your family or group of up to 14 people and features a heated private pool* and a short walk to the beach. Sur Le Mer is located just steps from beach access and right next to Chaplin Community Park (basketball, playground, tennis, baseball diamond and open field). It's also short drive to local restaurants, bars, grocery store

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.

5 out of 5 average rating, 105 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!

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.

5 out of 5 average rating, 120 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.

A bright dining area offers a view of the ocean through open doors leading to a private beachfront balcony. Coastal décor is present on the round table, complemented by neutral tones and natural light streaming in from the outdoors.

4.98 out of 5 average rating, 361 reviews

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar & Grille KING BED FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

The private heated pool area features a calming blue water surface surrounded by a stone patio. Five lounge chairs are positioned for relaxation, and a grill is located nearby, with lush greenery providing a natural backdrop and a view of the golf course beyond.

4.86 out of 5 average rating, 119 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.

The open-concept living space features handmade Saltillo tiles and a vaulted ceiling. A comfortable couch and a fireplace are visible along with a large dining table. A staircase leads to the upper level, enhancing the spacious layout. Sliding glass doors provide access to the outdoor area.

4.98 out of 5 average rating, 107 reviews

Governor’s Quarters Pet Friendly, Fenced in Yard

Welcome to Governor's Quarters- your Luxury Hilton Head Getaway Stay Lowcountry in this stately-designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from the SeaPines Beach Club and HarbourTown Golf Links and the heated community pool! Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, HarbourTown Lighthouse, & most importantly- the beach!

5 out of 5 average rating, 20 reviews

Palmetto Dunes Beach House

Completely Renovated, designer decorated home with private pool/built in spa. One level EASY walk to the beach (15 mins) ...or call the Dunes Buggy, free of charge, to pick you up and bring you back! Open floor plan with large bedrooms (King, Queen, 3 Doubles). Plenty of space inside and out to relax. Situated on a body of water overlooking the the 9th hole of Robert Trent Jones Golf Course. pool/spa -extra fee Bring the whole family to this great place with lots of room for fun.

4.96 out of 5 average rating, 164 reviews

Aerial view captures the lush greenery surrounding the property, with tree canopies creating a natural border. A highlighted path directs toward the beach, while the serene lagoon is visible nearby, surrounded by the abundant foliage and manicured landscape.

Townhouse in Shipyard

Beachfront Resort 2B Golf Beach Pickleball Tennis

✨Top 10% Guest Favorite✨ Gated Beachfront Resort Golf, Tennis, Pickleball, Pool, Restaurants & Bars Gorgeous Sunny Villa Panoramic Lagoon & Golf Views! Beautiful & Lush Scenery Huge Old Oaks dripping in Spanish Moss! Walk/Bike to Beach Abundant Wildlife! Walk to Shipyard Golf Club & Pub! Modern Coastal Sunny 1st Floor KING BED Master 3 XL SmartTVs WIFI 287 mps Fully Stocked Kitchen Walk-in Shower Washer/Dryer Beach Chairs, Boogie Boards & More! BBQ Bike & Walk Paths Close to Coligny!

A wooden boardwalk leads through grassy dunes towards the beach. The path extends toward the calm ocean, under a gray sky. Soft sand is visible at the boardwalk's end, inviting guests to access the beachfront.

4.96 out of 5 average rating, 367 reviews

Ocean View & Steps to Beach! Remodeled HHBT Condo!

Newly remodeled! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

Villa in Hilton Head Island

The outdoor space features a year-round heated pool surrounded by lush greenery, with a clear view of the ocean. Umbrellas offer shade over picnic tables, while tall trees enhance the serene atmosphere of the beachside setting.

4.97 out of 5 average rating, 127 reviews

Oceanfront Scandi Oasis Amazing View & Heated Pool

Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

4.75 out of 5 average rating, 4 reviews

Luxury Sea Pines Home w Pool | Steps to Beach | 12

Welcome to your Sea Pines escape, nestled beneath a canopy of live oaks just a short walk to the beach. This inviting retreat sleeps up to 12 guests and blends modern coastal style with relaxed Lowcountry charm. Enjoy a private patio with lagoon views, a pool and spa, and outdoor spaces perfect for unwinding after a day in the sun. With easy access to beaches, golf, and biking paths, this home offers the ideal setting for a memorable Hilton Head getaway.

Popular amenities for Hilton Head Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.99 out of 5 average rating, 145 reviews

Beach condo with pool and stunning nature views

A spacious living area is accentuated by vaulted ceilings and large windows, allowing natural light to fill the room. Comfortable sofas are arranged around a central coffee table, with decorative cushions adding color. A lamp and a decorative vase create a welcoming ambiance in this inviting space.

4.95 out of 5 average rating, 133 reviews

Lovely 3BR in Palmetto Dunes w/ new pool & spa

A spacious living area is equipped with two grey sofas adorned with striped cushions, positioned around a wooden coffee table with a glass top. Subtle artwork hangs on the wall, complementing the light decor, while natural light illuminates the room from nearby areas.

4.81 out of 5 average rating, 183 reviews

After Dune Delight | Spacious Condo, Full Kitchen

Villa in Hilton Head Island

A comfortable seating area includes a cozy gray sofa with patterned throw pillows. A bamboo coffee table sits in the center, surrounded by natural light from sliding glass doors leading to a balcony. Vibrant green plants add a touch of nature to the space.

4.96 out of 5 average rating, 216 reviews

Private Beach on Sound | 3 Pools/Spa | Free Tennis

4.94 out of 5 average rating, 122 reviews

The living area is furnished with a spacious sectional sofa, accented by decorative pillows and a cozy throw. A large television is mounted on the wall, and floor-to-ceiling windows provide an ocean view, allowing natural light to fill the room.

Condo in Palmetto Dunes

Ocean Views at Villamare 1404, Steps to the Beach!

4.96 out of 5 average rating, 112 reviews

Condo in Palmetto Dunes

Oceanside Resort - Private Beach Access - 3 Pools

A modern kitchen is illustrated with granite countertops and sleek cabinetry. Stainless steel appliances, including a microwave and oven, are visible. A large island with seating for three complements the space, which transitions into a cozy dining area beyond, illuminated by overhead lighting.

4.94 out of 5 average rating, 213 reviews

Coastal Beach Getaway for Sunsets & Flip Flops HHI

A modern kitchen features stainless steel appliances, complemented by white cabinetry and granite countertops. An open dining area is visible, with a wooden table surrounded by chairs, and a cozy living space includes a comfortable sofa facing a wall-mounted TV. Large windows offer ocean views.

4.95 out of 5 average rating, 121 reviews

Ocean View with Beach Access

Family- and pet-friendly home rentals

Luxe

Villa in Sea Pines

5 out of 5 average rating, 12 reviews

100 Fairway Lane, Sea Pines: A Luxury Villa Stay

A well-lit bedroom features two spacious beds, each adorned with vibrant blue and green bedding. A decorative wall basket adds a natural touch, while a window with patterned curtains allows for natural light. A small chair and side table enhance the room's functionality.

4.99 out of 5 average rating, 114 reviews

6 BR, Sleeps 26, Beach Time

A charming beach cottage is framed by mature trees and lush landscaping. A pathway of gravel leads to the entrance, featuring a well-maintained lawn. An American flag is displayed prominently, enhancing the welcoming atmosphere of the exterior.

4.99 out of 5 average rating, 67 reviews

80 Steps to Private Beach Access • Walk to Coligny

Cottage in Hilton Head Island

An open concept living area features a large flat-screen TV mounted on a white entertainment unit, surrounded by books. Light-colored furniture is arranged comfortably, with a tufted ottoman in the center. The kitchen area is visible in the background, showing modern appliances and island seating.

4.83 out of 5 average rating, 103 reviews

New Cottage: 4th row & fully fenced back yard!

The outdoor area features a private pool surrounded by palm trees, with a spacious deck. Comfortable loungers and umbrellas are arranged nearby. Two inflatable swan floats rest on the water's surface, adding a playful touch to the serene setting.

4.94 out of 5 average rating, 53 reviews

5BR Private Pool+Hot Tub+Sauna, 400 Steps to Beach

4.91 out of 5 average rating, 141 reviews

The exterior of the cottage is depicted, showcasing a two-story design with light-colored siding, surrounded by landscaped shrubs and greenery. A pathway leads to the entrance, flanked by a wooden railing, inviting access to the home.

Cottage in Shipyard

Shipyard! - Private Beach & Golf! Pet Friendly!

5 out of 5 average rating, 8 reviews

Palmetto Dunes Villa – Golf, Pools & Bike to Beach

5 out of 5 average rating, 6 reviews

Eight Palms | Pet-Friendly 4BR Single Level

Family-friendly home rentals with a pool

5 out of 5 average rating, 4 reviews

Luxury Dunes Paradise - Private Pool

A spacious pool area is visible, bordered by sun loungers and palm trees. The ocean can be seen in the background, with glistening sunlight reflecting off the water. A clear blue sky enhances the inviting atmosphere of the outdoor space.

4.91 out of 5 average rating, 234 reviews

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR

A private residence is set among tall trees, featuring a spacious patio area with a circular pool at its center. A barbecue grill and poolside loungers are visible, surrounded by natural landscaping, creating a serene outdoor retreat.

4.93 out of 5 average rating, 41 reviews

Starfish Beach House with Pool and Bikes

Apartment in Hilton Head Island

4.97 out of 5 average rating, 31 reviews

Stunning Ocean View | King Bed | Beach/Pool Resort

5 out of 5 average rating, 9 reviews

Home in Shipyard

Coastal Fairways

Apartment in Palmetto Dunes

5 out of 5 average rating, 4 reviews

Incredible Hilton Head condo - private beach!

Apartment in Hilton Head Island

5 out of 5 average rating, 7 reviews

Beachfront Condo w/ Pool · Hot Tub · Pickleball

An open-plan living area is featured, showcasing a spacious layout with multiple light-colored sofas arranged around a circular coffee table. A generous area rug complements the hardwood flooring. Natural light fills the room through large windows, while a modern ceiling fan provides a breezy atmosphere.