Family-friendly holiday rentals in Hilton Head Island

4.98 out of 5 average rating, 121 reviews

A lounge area features a comfortable sofa adorned with decorative cushions. A round coffee table sits in front of it, surrounded by a soft area rug. A large wall-mounted television is complemented by a striking maritime mural, while natural light filters through blue drapes.

Condo in Shipyard

Hilton Head Island VILLA: STEPS 2 Beach & Coligny!

Welcome to The Hilton Head Islander! A cozy retreat meticulously maintained for up to 6 guests. Situated in North Forest Beach, it's near Hilton Head's treasures beaches, bars, shops, and eateries. Enjoy a 6-min walk to the beach and the beautiful Celebration Park and 2-min walk to Coligny Plaza! Essentials like toiletries, Kcups, beach gear, & more are provided. While cozy with one bathroom, your comfort is guaranteed. Relax by the onsite pool and enjoy the spectacular beaches. Enjoy your stay!

A view from the balcony showcases lush greenery and a tranquil pond, with a gentle fountain visible. In the distance, the ocean glimmers under a blue sky. A palm tree stands prominently in the foreground, enhancing the coastal scenery.

4.91 out of 5 average rating, 289 reviews

Hilton Head Beach & Tennis Resort Ocean View!

AMAZING OCEAN VIEW FROM THE BALCONY! Newly remodeled! Perfect for a family or a couple looking to enjoy a great oceanfront resort! Enjoy the site and sounds of the ocean right from the balcony!! This condo is on the second floor with an ocean view, only 5 units back from the ocean, this is a PRIME location! The unit is located in a quiet part of the resort, steps away from the ocean, Resort Pool, Beach Bar w/live music. FREE Tennis and Pickleball courts. The resort has 24/7 onsite security.

4.95 out of 5 average rating, 109 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

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.

4.97 out of 5 average rating, 318 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!

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.

5.0 out of 5 average rating, 113 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.

5.0 out of 5 average rating, 123 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.

Villa in Hilton Head Island

A spacious oceanfront pool area is surrounded by lush green landscaping, featuring lounge chairs and a shallow entry. A winding path leads toward the beach, with the ocean visible in the background, flanked by tall trees creating a serene atmosphere.

4.95 out of 5 average rating, 146 reviews

Modern Oceanfront Villa With Views and Heated Pool

Welcome to Villa Lucia, our oceanfront retreat on S. Forest Beach. Enjoy the ocean views from the balcony and convenient year-round heated pool just outside your door. The villa has been fully renovated with modern amenities and has personal touches throughout. Our location is unbeatable on S. Forest Beach between Coligny Beach and Sea Pines - Away from the crowds, but close enough (.5 mi) to bike or walk to all that’s offered. After a long day enjoy a drink with lush foliage and sea views.

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, 116 reviews

6 BR, Sleeps 26, Beach Time

Just a short walk down Folly Field to the beach & locally managed by the Owner. This brand new beach house has 6 bedrooms and 4 full bathrooms. Linens, Bath Towel sets & Pool Towels included. An Amazing bunk room/play room with 6 full size bunk beds, high end furnishings, fully equipped kitchen, dining for the entire crew, 2 huge balconies with lovely lagoon views, large outdoor living area with television and shaded pool. We have thought of everything & we are at your service! PN: 040312

4.98 out of 5 average rating, 108 reviews

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.

Home in Sea Pines

Stately Governors Quarters-Pet Friendly, Fenced In

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!

5.0 out of 5 average rating, 103 reviews

Walk to Beach-Amazing New Home-Hot Tub-Heated Pool

Maximum 16 guests. Welcome to Sea Mist Manor-A quick walk to one of islands best beaches.. Our family has created an amazing ocean getaway. Featuring upscale furnishings & decor from local shops. Creature comforts include-high end hot tub-infra red sauna-arcade-fun kids room-golf themed room.. We welcome you with open arms to Sea Mist Manor-A Seaside Extravaganza! As seasoned hosts, achieving 8+yrs of Airbnb Super Host status, rest assured you're in good hands. Town Permit #053482

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, 377 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!

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.

4.99 out of 5 average rating, 451 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.

Popular amenities for Hilton Head Island family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 146 reviews

Spacious Villa in Hilton Head Resort! STR#024945

The private balcony features a dining table surrounded by chairs, offering serene lagoon views. Lush greenery frames the area, contrasting with the smooth wooden railing. Light filters through the trees, creating a peaceful outdoor setting, ideal for enjoying meals or morning coffee.

4.92 out of 5 average rating, 103 reviews

Island Club Condo: Beach, Pool, Gym, Pickleball

4.82 out of 5 average rating, 284 reviews

Condo w/ Indoor Pool and Hot Tub!! Beach Access🏝

A welcoming living area is furnished with a dark sofa and a light-colored armchair. A wooden coffee table sits in the center, complemented by decorative elements. A wall-mounted Smart TV is positioned across from the seating, and large windows allow natural light to brighten the space.

4.95 out of 5 average rating, 115 reviews

Lovely Beachside Villa w/ Resort Amenities

4.97 out of 5 average rating, 118 reviews

Oceanside Resort - Private Beach Access - 3 Pools

A scenic view of the ocean is displayed from a top-floor balcony. The tranquil water reflects the clear blue sky, while marshland and vegetation frame the landscape. A boardwalk is visible, leading toward the beach, enhancing access to the natural surroundings.

4.94 out of 5 average rating, 160 reviews

Gorgeous OCEAN Views! Resort Amenities & Beach!

4.83 out of 5 average rating, 288 reviews

Boardwalk to Beach, Pools, Hot Tub!

A bright entryway is presented, featuring turquoise walls and a matching front door. A white chair is adorned with a soft coral pillow, while a decorative wreath made of seashells hangs beside the door. A welcoming sign and a beach-themed tote bag add to the coastal decor.

4.99 out of 5 average rating, 108 reviews

Charming 3BR / 2 bath beach bungalow with hot tub!

Family- and pet-friendly home rentals

A bright living area is presented with a cozy arrangement of a spacious sofa and a gray loveseat. Natural light filters through window treatments, highlighting a round coffee table and decorative accessories. A console table with a mirror and a soft lamp complete the inviting space.

4.94 out of 5 average rating, 108 reviews

Hilton Head Island Beach Cottage/House

4.98 out of 5 average rating, 103 reviews

A charming circular home is nestled among tall trees, featuring a spacious deck with white lounge chairs. The wooden steps lead up to the entrance, showcasing large windows that allow ample natural light. The surrounding greenery enhances the sense of privacy and seclusion.

Treehouse in Sea Pines

Harbour Town Tree House | Private Office | HT Pool

4.9 out of 5 average rating, 104 reviews

A calm beach scene is captured at dusk, featuring gentle waves lapping at the shore. The horizon showcases a soft gradient of colors, transitioning from deep blue to warm peach and pink tones. The tranquil sea reflects the fading light of dusk.

Villa in Palmetto Dunes

Spacious dog-friendly villa, walk to the beach

A two-story house features a light-colored exterior with a metal roof and a front balcony. The driveway provides access to two garages, with landscaped greenery and grass surrounding the property, enhancing the overall curb appeal.

4.87 out of 5 average rating, 405 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King beds*grill*gms

4.94 out of 5 average rating, 237 reviews

Large home, beach close, pool

Superhost

A spacious screened porch equipped with a dining table and chairs offers a relaxing area for gatherings. Two ceiling fans provide comfort, and a fireplace adds a cozy touch. A large window showcases the private backyard, enhancing the connection to the outdoors.

Home in Shipyard

4.84 out of 5 average rating, 269 reviews

Private Beach Access-Pet Friendly-Hot Tub!

Superhost

Home in Palmetto Dunes

4.84 out of 5 average rating, 148 reviews

Blue Sky Villa: Beach/pets/golf/tennis/pickleball

4.85 out of 5 average rating, 156 reviews

An outdoor deck features a shapely pool surrounded by lounging chairs. Lush greenery and palm trees are visible in the background, offering a view of the golf course. A purple umbrella stands next to the pool, providing shade.

Home in Palmetto Dunes

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Family-friendly home rentals with a pool

The image displays a large swimming pool surrounded by lounge chairs, with a view of the sandy beach and ocean beyond. The shoreline features umbrellas for shade, while the landscape includes greenery and distant beachgoers enjoying the sun.

4.76 out of 5 average rating, 155 reviews

Relax and Unwind at this Ocean Front Resort

Townhouse in Palmetto Dunes

4.96 out of 5 average rating, 105 reviews

Steps to Pool + Private Beach | Baby Gear!

A light-filled living area features a cozy seating arrangement with a white sofa and a coffee table. The kitchen can be seen in the background, highlighting modern cabinetry and a casual dining setup. Natural textures are present through the woven rug and wood accents.

4.83 out of 5 average rating, 193 reviews

Close to BEACH bar&grill! Sleeps 6, 2 bed 2 bath!

Superhost

A serene beach scene features gentle waves lapping at the shore under a soft pastel sky. The moon hovers above the horizon, casting a warm glow over the water. A distant figure is seen walking along the wet sand, contributing to the tranquil atmosphere.

4.89 out of 5 average rating, 251 reviews

Oceanside Beach Retreat

A private pool area is featured, showcasing a clear blue pool surrounded by paved decking. Several lounge chairs are positioned nearby, accompanied by a shaded cabana area with seating. Bright pink inflatable flamingos float in the water, enhancing the relaxing ambiance.

4.97 out of 5 average rating, 134 reviews

Resort-Style Pool, Cute House 88 Steps to Sand

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, 241 reviews

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR

4.96 out of 5 average rating, 169 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 Pool Pickleball

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.