Family-friendly holiday rentals in Hilton Head Island

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, 229 reviews

Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR

☀️Time to BOOK YOUR HILTON HEAD ESCAPE. Wake up to sweeping oceanfront views from this top-floor Breakers villa, where sunrise steals the show. Watch dolphins & sip morning coffee on your private balcony, then walk just steps to the beach, pool, restaurants, and shopping at Coligny Plaza—no car required. Perfect for a romantic getaway or small family vacation, with exclusive deals on bikes & dolphin tours. This bright condo offers unbeatable location, privacy, and a stress-free island stay. 🐬🚲

A private balcony overlooks a pool surrounded by lounge chairs and lush greenery. The ocean is visible in the distance, framed by tall trees under a clear blue sky. The space includes a small round table with two chairs.

4.9 out of 5 average rating, 173 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

Welcome to Ocean Pearl Villa. Sit back, relax and listen to the crashing of the waves, while relaxing on your private balcony of our two bedroom, two bath beautiful oceanfront condo. Ocean Pearl is located in Beachwood Place, a 24 unit gated private complex, on Hilton Heads finest South Forest Beach & only 3 minute walk to Coligny Plaza, the heart of Hilton Head's restaurants, Shopping & family activities. You will enjoy the wonderful accommodations and spectacular views at 2H Beachwood Place.

Townhouse in Hilton Head Island

A light and airy living space is highlighted by a comfortable sofa, accompanied by two round armchairs in warm tones. A glass coffee table sits in the center, and natural light filters in through the window, creating a cozy atmosphere.

4.89 out of 5 average rating, 112 reviews

Updated Townhome Near the Beach, Tennis, and Golf

Spacious townhome style retreat just five minutes away from the beach in relaxing Hilton Head Island. This location is hard to match: neighborhood includes lots of shopping, dining, and entertainment options nearby (with a movie theatre and international cuisine literally across the street), as well as tennis courts and golf courses in the area. A convenient bike trail passes right by our door and takes you to the beach in ten minutes. Relax, refresh, recharge... just have a great time here!

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.

4.99 out of 5 average rating, 125 reviews

Ocean View KING BED 75"TV Beach Bar Pickleball GYM

✨Top 5% Airbnb Home✨ BIG OCEAN VIEWS FROM LIVING ROOM & BALCONY! Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar! FREE Pickleball, Tennis, Gym & More HGTV Featured Decorator 100% NEW Luxury renovation KING BED + 75" & 65" Smart TVs Expanded Bedroom Luxe 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

4.74 out of 5 average rating, 119 reviews

A spacious living area features a bright and airy ambiance with two comfortable sofas and an armchair arranged around a coffee table. A large sliding glass door creates a connection to the outdoors, offering views of the lush surroundings. A dining area with bar stools is visible in the background.

Apartment in Sea Pines

Lovely Villa in Sea Pines Hilton Head

🌊 🌴 Location, location, vacation! Welcome to your dream getaway in Bluff Villas, where everything you love about Hilton Head is just steps away. This sunny and spacious 2-bedroom, 2-bath condo is perfectly situated just a minutes walk to the beach, South Beach Marina, the iconic Salty Dog Café, and the South Beach Pool (reopening Summer 2025)! Relax on your private patio overlooking Braddock Cove, unwind in the updated living space, or take a quick stroll to grab an ice cream by the harbor.

A tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.

4.97 out of 5 average rating, 305 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!

4.92 out of 5 average rating, 190 reviews

A cozy living room features a modern fireplace and a large flat-screen TV mounted on the wall. Light enters through expansive sliding glass doors, leading to a deck. Comfortable seating is arranged around a circular coffee table, with decorative pillows adding subtle touches.

Townhouse in Sea Pines

Ocean Gate 13 Walk to beach villa with pickleball

This villa is perfect for the family beach vacation! We have little ones ourselves, so we've got all the gear needed to make this a comfortable and relaxing stay. We LOVE this villa because of its screened in porch, FREE TENNIS, and proximity to the beach. The screened in porch allows you to enjoy breakfast and happy hour free from mosquitoes and close enough to hear the waves! The beaches are far less crowded than other areas of the island, and it's very close to Sea Pines and Coligny Plaza.

4.98 out of 5 average rating, 104 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

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!

Cottage in Hilton Head Island

A two-story house is shown with a yellow exterior and a wide deck featuring two red umbrellas. The space underneath the deck is open, with parking for vehicles visible on a concrete driveway surrounded by green grass and landscaped areas.

4.97 out of 5 average rating, 111 reviews

Burkes Beach House - 2nd Row to Beach #023021

Our home is second row at Burkes Beach. Close to Palmetto Dunes Plantation Golf and Tennis , Port Royal Plantation Golf and Tennis. Convenient mid Island location. It is great for couples, solo adventurists, and families (not set up for toddlers and younger). Steps to the beach path and Chaplin Park, which has lit tennis courts, park and picnic areas. Walk or bike on beach to Coco's Beach Bar or Marriott Beach Bar. Open floor plan and under house parking. OWNER IS A LICENSED REALTOR.

Apartment in Palmetto Dunes

From the balcony, a panoramic view of the heated outdoor pool is visible, surrounded by lounge chairs. The backdrop features lush palm trees and the serene coastline. Beyond, the tennis courts and the nearby boardwalk meander through marshlands, leading to the tranquil beach at sunset.

4.97 out of 5 average rating, 124 reviews

Gorgeous 2 Bedroom Condo - Pool/Tiki Bar/ Beach

Welcome to your Gorgeous Beachside Condo! Come stay at our beautiful coastal condo at the Gated Hilton Head Resort. Your 2 Bedroom, 2 Bath Villa sleeps up to 6 people. Located Mid-Island; close to EVERYTHING! *2 Outdoor Pools *1 Heated Indoor Pool *Hot Tub *Sauna *6 Tennis Courts *Fitness Center *Badminton Court *Volleyball *Picnic Area *Poolside Deli *Cabana Bar *Boardwalk to the Beach *Coco's Bar & Grill *Elevators *On-site Shop, Bike Rentals, & Laundry *Free Parking

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, 357 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 serene beach scene at sunset displays soft hues of orange and pink reflecting on the water. Two figures stroll along the shoreline, leaving footprints in the sand. Gentle waves lap against the beach, creating a peaceful coastal atmosphere.

4.9 out of 5 average rating, 186 reviews

Cozy in Coligny

Welcome to the Cozy in Coligny condo! Located at The Breakers, a highly desirable beachfront property, you are only steps away from the pool and beach. You will be in the heart of award-winning Coligny Beach – park your car and leave it! You can spend the day playing in the sun and sand then walk across the street to Coligny Plaza – home to the beloved Piggly Wiggly grocery store and 60+ shops, restaurants, entertainment, tour information, beach equipment, and bike rentals.

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, 140 reviews

Beach condo with pool and stunning nature views

Flat in Hilton Head Island

Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.

4.83 out of 5 average rating, 192 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

The living area features a reclining leather sofa and a coffee table made of wood. A flat-screen TV is mounted on the wall, complemented by light teal walls that enhance the airy feel. A chair sits nearby, providing additional seating.

4.94 out of 5 average rating, 124 reviews

HHR Building 1-Heated Outdoor Pool-Walk to Beach

Apartment in Palmetto Dunes

A sandy beach scene features a line of blue umbrellas providing shade over a row of wooden chairs. Gentle waves roll in from the ocean under a clear sky, while a distant red lighthouse is visible on the horizon.

4.86 out of 5 average rating, 158 reviews

Beach Resort, pools, tennis, pickle ball Tiki bar!

A comfortable bedroom features a spacious bed adorned with white and blue striped bedding. Two bedside lamps provide gentle lighting beside the bed, while a large mirror reflects the room’s arrangement. Windows allow natural light to illuminate the space, highlighting the soft gray carpeting.

4.91 out of 5 average rating, 185 reviews

Beach condo in gated resort w/ tons of amenities!

Apartment in Palmetto Dunes

A calm bedroom features a spacious bed with a pink patterned quilt, complemented by a decorative beach-themed sign above. Two white closet doors are visible along one wall, while a bedside table holds a lamp. Coastal decor accents enhance the serene atmosphere.

4.9 out of 5 average rating, 268 reviews

HHI. Easy Direct Beach Access. 3 pools- 1 indoor.

A dining area features a wooden table set for six, accompanied by white chairs. Natural light flows through the window, illuminating the adjacent modern kitchen with stainless steel appliances and light cabinetry. A comfortable seating area is visible in the background.

4.8 out of 5 average rating, 265 reviews

Pool side condo just steps from beach boardwalk!

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.

4.96 out of 5 average rating, 104 reviews

Lovely Beachside Villa w/ Resort Amenities

Family- and pet-friendly home rentals

Home in Hilton Head Island

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, 117 reviews

98 Sandcastle Ct

4.98 out of 5 average rating, 118 reviews

A spacious deck features a circular fire pit surrounded by four wooden adirondack chairs with cushions. A striped pouf adds comfort to the area. Scenic sunset views over the beachfront landscape create a serene backdrop.

Chalet in Sea Pines

180º Ocean Views, Treehouse "Siren's Lookout"

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.

4.84 out of 5 average rating, 100 reviews

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

Guest house in Hilton Head Island

4.92 out of 5 average rating, 291 reviews

Alli B's Air B and B-Great Country access off 278

4.98 out of 5 average rating, 96 reviews

A bright living area is filled with soft furnishings in soothing tones. Two comfortable couches are positioned around a central coffee table, while light streams in through sliding glass doors that open to a private patio. Decorative beach-themed artwork adds a touch of coastal charm.

Villa in Sea Pines

HHI South Forest beach/WLK TO BEACH, dining, pool

A serene pool area is surrounded by lush greenery, with a paved walkway leading to the water. Several lounge chairs are positioned near the pool, which is framed by a low fence. Mature trees provide ample shade, enhancing the tranquil atmosphere.

4.85 out of 5 average rating, 193 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Superhost

Treehouse in Sea Pines

5 out of 5 average rating, 3 reviews

Waterfront Tree House | HT Pool | Harbour Town 24

Home in Hilton Head Island

4.93 out of 5 average rating, 228 reviews

Beach close, heated pool, golf cart avail to rent

Family-friendly home rentals with a pool

Superhost

Apartment in Sea Pines

4.71 out of 5 average rating, 7 reviews

Marriott's Monarch at Sea Pines 2BD

Flat in Hilton Head Island

5 out of 5 average rating, 8 reviews

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

A cozy living area features a comfortable blue sofa and a wooden coffee table, complemented by decorative accents. A flat-screen TV is mounted on the wall, and large windows open to the patio. A welcoming ambiance is created by soft lighting from a nearby lamp.

4.95 out of 5 average rating, 22 reviews

Beach View - 1st Floor - King Bed - Pools -Tennis

4.96 out of 5 average rating, 77 reviews

Sea la Vie @Fiddler's Cove - Fitness Room

4.91 out of 5 average rating, 11 reviews

Flat in Palmetto Dunes

Ocean Cove condo. Lagoon views close to beach/pool

Superhost

5 out of 5 average rating, 3 reviews

MyStay at 136 Shorewood | Ocean+Pool Views in SFB!

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.

4.9 out of 5 average rating, 239 reviews

Oceanside Beach Retreat