Family-friendly holiday rentals in Hilton Head Island

4.98 out of 5 average rating, 164 reviews

A wooden boardwalk leads to a sandy beach, where beach umbrellas dot the shoreline. Soft waves lap at the shore beneath a clear blue sky with fluffy clouds, creating a serene coastal scene.

Townhouse in Shipyard

Beachfront Resort 2b Golf Lagoon Pickleball Tennis

✨Top Airbnb Guest Favorite Home✨ Gated Beachfront Golf Resort! Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis - across street HGTV Decorator designed Panoramic Golf & Lagoon Views XL Double Porch Lush Scenery - Tons of Wildlife! Coastal Décor Sunny 1st Floor End Unit KING BED + 2 QUEENS 3 XL SmartTVs FAST WIFI & CABLE Chef's Kitchen Washer/Dryer BBQ Beach Cart, Chairs, Boogie Boards, Ice Chest Walk/Bike to Beach Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

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, 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!

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, 99 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!

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, 118 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.

4.97 out of 5 average rating, 356 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 FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED 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 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, 105 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!

4.96 out of 5 average rating, 158 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, 360 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, 125 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.

A stunning sunrise illuminates the ocean, casting a warm golden glow across the water's surface. Rays of sunlight stretch outward, reflecting off the gentle waves. The shoreline is visible, framed by soft grasses, enhancing the tranquil morning scene.

4.99 out of 5 average rating, 198 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, 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! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! 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**

Apartment in Hilton Head Island

A newly renovated kitchen area features gray cabinets, a modern stovetop, and stainless-steel appliances. A comfortable sofa is positioned near a light-colored coffee table. Natural light illuminates the space, highlighting the wood flooring and a decorative area rug with a coastal design.

5 out of 5 average rating, 30 reviews

Seaside Villas Escape full condo 1 bedroom + bunks

Seaside Escape offers a completely renovated one bedroom that is right on the beach! Enjoy everything Hilton Head has to offer with this one of a kind escape. Located right near cologny plaza you will be perfectly located for all activities on and off the beach. Seaside escape offers one bedroom with a queen bed, two bunk beds for kids, and a pull out couch. the newly renovated layout maximizes the space to ensure the most comfortable stay at Seaside Villas.

5 out of 5 average rating, 120 reviews

Condo in Sea Pines

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.

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, 141 reviews

Beach condo with pool and stunning nature views

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, 177 reviews

After Dune Delight | Spacious Condo, Full Kitchen

4.94 out of 5 average rating, 121 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, Steps to the Beach!

The living area showcases comfortable seating arrangements with two plush sofas and an accent chair. A light area rug features a subtle pattern. Large glass doors invite natural light and connect the space to an outdoor balcony. Art adorns the walls.

4.96 out of 5 average rating, 116 reviews

Private comfy condo, steps away from the beach

4.85 out of 5 average rating, 122 reviews

A private balcony features comfortable seating with decorative cushions and a small round table. The view showcases a serene landscape of marshland and trees under a colorful sky at sunrise, providing an opportunity for tranquil outdoor relaxation.

Condo in Palmetto Dunes

Stunning Ocean & Coastal Views | Resort Perks!

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, 187 reviews

Beach condo in gated resort w/ tons of amenities!

A balcony offers a table and two chairs, providing a space for relaxation and enjoyment of ocean views. The horizon features a clear blue sky and the serene expanse of water. Lush greenery and trees frame the scenery, enhancing the tranquil atmosphere.

4.86 out of 5 average rating, 100 reviews

Jim's Chic Direct Oceanfront 2BR Villa

4.93 out of 5 average rating, 241 reviews

Condo in Palmetto Dunes

Tasteful & Clean! Walk to Beach/3 Pools/Pickleball

Family- and pet-friendly home rentals

Home in Hilton Head Island

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, 113 reviews

6 BR, Sleeps 26, Beach Time

Superhost

4.8 out of 5 average rating, 5 reviews

Wren's Nest - 4BR SeaPines Retreat+Backyard Oasis

4.85 out of 5 average rating, 150 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

4.91 out of 5 average rating, 138 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!

Home in Hilton Head Island

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, 396 reviews

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

5 out of 5 average rating, 20 reviews

Private Oasis w/ Pool ~ Pet Friendly ~ Fenced Yard

4.91 out of 5 average rating, 33 reviews

A living area is furnished with plush, neutral-toned seating that provides comfort. A large glass door reveals views of the tranquil outdoor space. Art and a wall-mounted television enhance the atmosphere, while a dining area is visible in the background.

Condo in Sea Pines

SeaPinesVilla - Harbor Town, Free Bikes, Pets OK

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.

4.86 out of 5 average rating, 194 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Family-friendly home rentals with a pool

5 out of 5 average rating, 7 reviews

A spacious backyard features a free heated pool with a paved surrounding. A cozy fire pit made of stone is accompanied by four comfortable chairs, perfect for gatherings. Lush greenery and palm trees provide a natural setting, while the home offers large windows overlooking the area.

Home in Palmetto Dunes

Palmetto Dunes Escape with Pool | Dock | Firepit

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.

4.92 out of 5 average rating, 39 reviews

Starfish Beach House with Pool and Bikes

Apartment 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.

4.96 out of 5 average rating, 25 reviews

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

4.96 out of 5 average rating, 57 reviews

Oceanfront Luxe KING BED 75TV Beach Bar Pickleball

4.96 out of 5 average rating, 78 reviews

Sea la Vie @Fiddler's Cove - Fitness Room

An ocean view is captured from the fifth floor, showcasing a sandy beach with gentle waves lapping at the shore. Lush greenery and a playground area are visible in the foreground, framed by nearby buildings and an inviting blue sky.

4.97 out of 5 average rating, 75 reviews

Island Club 4502-Beautiful Ocean View