Family-friendly holiday rentals in Hilton Head Island

A cozy living area features a spacious gray sofa with decorative pillows. Soft lighting from two side lamps illuminates the room. Large sliding glass doors open to a deck, providing a view of the surrounding trees. Wall art depicting a turtle adds a touch of character.

4.96 out of 5 average rating, 122 reviews

Cozy Villa 6 Minute Walk From the Beach & Golf

Recently updated villa only a 6 min. walk to the beach with private & public beach access and a 7 min. drive to Port Royal Plantation GC. Villa has 1 queen and 2 twin beds, full size sleeper sofa, 55" tv in the living room and tvs in both bedrooms. Many family amenities, Washer/Dryer in the unit, and a deck overlooking the Port Royal golf course. Fiddler's Cove is a gated community with 10 Har-Tru tennis courts, 2 indoor racquet ball courts, 2 pools, hot tub, work out facility and Tot lots.

Guest suite in Shelter Cove

An aerial view captures a cluster of modern buildings with red roofs, surrounded by lush greenery. Sailboats are docked in the marina, with a scenic waterfront area in the background. A glimpse of residential areas and palm trees adds to the inviting atmosphere.

4.93 out of 5 average rating, 365 reviews

Prime Spot: Harbour, Dining, Shops & Beach

Stay in the heart of it all at this upscale, centrally located guest suite (256 sq ft) with independent entrance, total privacy, queen bed and full bath (no kitchen). Step outside to waterfront restaurants, live music, bars, shops, and summer weekly fireworks. Supermarkets and more dining are just a 10-minute walk away. Enjoy a free shuttle to attractions within 2-mile radius (April–September). Golfing, biking, fishing, and water sports all nearby, free access to Palmetto Dunes Beach community.

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, 339 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! 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 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, 106 reviews

Luxury OceanView KING BED 75"TV Gym BAR Pickleball

✨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

4.92 out of 5 average rating, 123 reviews

A spacious living area is highlighted by large sliding doors opening to a serene outdoor view with palm trees. A modern sectional couch occupies the room, complemented by a coffee table and natural light filtering through soft gray curtains. A television is positioned against the wall.

Townhouse in Shipyard

Beach, pool, golf - 3 king bed master suites

Located on the Shipyards golf course with picturesque views of palm trees, overlooking the lake and fairways, the villa is adjacent to tennis, pool and a short walk or 5 min bike ride to the private Beach Club and the stunning sandy beach. With 3 spacious master suites, king beds, private ensuite and balconies, your family (6 adults/2 children) will feel right at home in this newly renovated, beautifully furnished villa. Enjoy your vacation with all the amenities at this centrally located home.

An inviting living space features a sectional sofa, a wooden coffee table, and a dining area with several chairs. Natural light illuminates the room through multiple windows, highlighting the coastal-inspired decor and airy layout. A chandelier complements the open, relaxed atmosphere.

4.91 out of 5 average rating, 124 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Offered by owner /manager. Master bath w/ walk in shower, spacious bright open concept LR, DR, kitchen, w/ private cozy courtyard. Designer inspired coastal chic for the beachy atmosphere. Sit and relax in the courtyard, lounge in the sun while having an afternoon drink and BBQ. Watch golfers at the driving range or Trent golf course just a short walk from the villa. Go for a swim in 1 of 5 community pools. Under 10 minute walk to Palmetto Dunes beach or call seasonal dune buggy for a ride.

4.95 out of 5 average rating, 114 reviews

Wide Ocean View 65"TV Pickleball BAR GYM Tennis

✨ Top 1% Airbnb Guest Favorite ✨ Wide Ocean View from Living Room & Balcony! Oceanfront Building Steps to Beach & Pool Updated by HGTV Decorator FREE: Pickleball, Tennis, Gym, Volleyball + More Top Floor w/Elevator Hear the Waves 2 XL SmartTVs Beach Chairs, Ice Chest & More Couples Retreat / Small Families RESORT: Oceanfront Pool w/Tiki Bar & Grille! Sports Bar w/Pool Table 3 Restaurants Bike Rentals on Site 2nd Pool Huge ShadyPlayground 3 BBQ Areas Gated 24/7 Security 4 Beach Boardwalks

Flat in Hilton Head Island

The entrance to Courtside Villas is marked by a prominent sign, featuring the name against a backdrop of lush landscaping. Tall palm trees and colorful flowers border the entrance, creating a welcoming approach along the tree-lined road.

4.94 out of 5 average rating, 162 reviews

Walk to Beach from Courtside Villas

Our spacious two bedroom, 2 ½ bath villa overlooks a large swimming pool, and comfortably accommodates six people. It is fully equipped and tastefully furnished to be a home-away-from-home. The kitchen has an electric range and oven, a microwave, refrigerator, dishwasher, disposal, washer and dryer. There is seating for six at the dining room table. The living room entertainment center has a Smart TV connected to cable and WiFi. Please note--Courtside has a strict No Pets policy.

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.

4.96 out of 5 average rating, 111 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 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, 274 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 and steps away from the ocean, resort pool, tennis and pickle ball courts. The resort has 24/7 onsite security

Townhouse in Hilton Head Island

A spacious living area features a light gray sectional sofa arranged around a neutral area rug. A blue accent chair adds contrast, while a round side table and lamp provide soft lighting. Natural light enters from the window, illuminating the room and creating a welcoming atmosphere.

4.83 out of 5 average rating, 113 reviews

{WHITE SANDS} : 2 Bedroom Beach Haven!

This South Forest Beach unit is just steps to the beach & about an 8 minute walk to Coligny Plaza. Our unit sleeps 6, with a King & 2 Queens. Includes many updates throughout & a private washer/dryer. Included is a large shared pool & also a children's pool w/ a beautiful serene patio area. ~ Traveling with a large group? Depending on availability, it may be possible to coordinate booking the unit next to me for a close, convenient stay for all to stay nearby!

A panoramic view from the balcony showcases the sparkling ocean and expansive blue sky. Below, palm trees dot the landscape, while the beach is glimpsed in the distance. A pool area is visible, framed by well-maintained greenery, with parking spaces filled with vehicles.

4.98 out of 5 average rating, 178 reviews

Luxury KING BED 65"TV Bar FREE Pickleball & Gym

✨Airbnb Top 5% Guest Favorite✨ Oceanfront Building! BIG Ocean Views Steps to Beach & Pool 100% NEW HGTV Designer Renovation! KING BED FREE Gym, Pickleball, Tennis Basketball, Volleyball Two 65" SmartTVs Beach Chairs, Boogie Boards, Ice Chest & More! Marble Kitchen/Spa Bath Quiet Top Floor Elevator RESORT: Huge Oceanfront Pool Tiki Beach Bar & Grille (Mid Feb-Nov) Sports Bar Bike Rental Gated 24/7 Security Free Island Trolley (Apr-Sept) 4 Beach Boardwalks

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 sandy path leads to the beach, flanked by dunes and coastal vegetation. The blue ocean stretches into the distance under a partly cloudy sky. A wooden railing guides the way down to the shore, where gentle waves meet the sand.

4.93 out of 5 average rating, 123 reviews

Sea Gem - Unwind by Sea in Style

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, 125 reviews

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

The kitchen and dining area is equipped with modern appliances, including a microwave and coffee maker. A wooden table with six chairs is set for dining, while white cabinetry and light countertops create a spacious atmosphere. A sliding door provides access to the outdoor area.

4.97 out of 5 average rating, 106 reviews

1st Floor, 8 Min Walk Beach, King Bed, In Unit W/D

A renovated kitchen features modern stainless steel appliances including a microwave, oven, and dishwasher. White cabinetry and granite countertops create a clean aesthetic. Ample storage is provided by drawers and cabinets, while laminate flooring adds a warm touch to the space.

4.99 out of 5 average rating, 209 reviews

1st Floor-Beach Access-2 Pools-Hot tub-Pickleball

Superhost

4.81 out of 5 average rating, 162 reviews

Beach Front Villa Oak Tree Lined Views to Water

A cozy living area is depicted with a patterned sofa and a wooden coffee table. A large wall mirror reflects light, while a ceiling fan adds comfort. Natural light enters through sliding glass doors, leading to a balcony view. A television is mounted on the wall, displaying programming.

4.78 out of 5 average rating, 227 reviews

Family Getaway for Making Memories Together

A serene beach scene at sunset, where the sky is filled with hues of orange and gold. The calm water reflects the vibrant sky, and footprints are visible in the fine sand leading along the shoreline.

4.96 out of 5 average rating, 139 reviews

Lovely family Villa Close to Beach

The living area features a sectional sofa with blue and neutral throw pillows. A textured round coffee table sits in front, surrounded by two accent chairs. Decorative wall art, consisting of various woven circles, adds visual interest. Light from table lamps enhances the inviting space.

4.94 out of 5 average rating, 135 reviews

Oceanfront Breathtaking Views

Family- and pet-friendly home rentals

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, 102 reviews

6 BR, Sleeps 26, Beach Time

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, 106 reviews

98 Sandcastle Ct

4.98 out of 5 average rating, 108 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 Harbour Town

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

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.

4.85 out of 5 average rating, 147 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

A modern three-story home is set within a lush, wooded landscape. The structure features blue siding, white trim, and large windows. A spacious driveway leads to a two-car garage, with an outdoor light fixture adding a welcoming touch to the entrance.

4.95 out of 5 average rating, 170 reviews

Beach close, pool, free golf cart included-79

Guest house in Hilton Head Island

A combined living and sleeping area features a gray couch with decorative pillows, a small coffee table, and a light-colored area rug. A twin bed with a white quilt and pillows is visible in the background, with large windows draped in yellow curtains allowing natural light to enter.

4.92 out of 5 average rating, 263 reviews

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

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, 178 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

4.87 out of 5 average rating, 134 reviews

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

Family-friendly home rentals with a pool

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.

5 out of 5 average rating, 14 reviews

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

4.89 out of 5 average rating, 9 reviews

Villa in Sea Pines

Updated Sea Pines Villa • Walk to Harbour Town

An aerial view captures the oceanfront condo nestled among lush greenery, with direct beach access leading to soft sandy shores. Umbrellas and beach chairs dot the shoreline, while a sparkling pool is visible within the resort's grounds, framed by tropical landscaping.

4.96 out of 5 average rating, 25 reviews

Oceanview Escape: Steps from the Beach & Pool

A screened-in porch is shown with comfortable seating arranged around a central coffee table, featuring blue accent pillows. Large windows offer a view of the private pool and lush greenery outside, filling the space with natural light.

4.94 out of 5 average rating, 17 reviews

5 Bedroom, Dual Family set-up, 5 mins from beach

Villa in Hilton Head Island

A comfortable living room features a large gray sectional sofa adorned with yellow and blue accent pillows. A wooden coffee table sits in front, with a decorative tray on top. A wall-mounted television is positioned across from the seating area, with natural light flowing through sliding glass doors.

4.8 out of 5 average rating, 20 reviews

Aurelia @ Hilton Head: Beach Pool Park Dine

4.93 out of 5 average rating, 30 reviews

A private pool area is surrounded by lush greenery and tall trees, providing privacy and a natural setting. The pool features a built-in spa and is bordered by a spacious stone patio. Four lounge chairs are positioned nearby for relaxation.

Home in Shipyard

Private Pool/Spa | Golf | Exq. Coffee | Seascape

4.92 out of 5 average rating, 25 reviews

Turtleville - Queen bed+kid bed Renovated in 2025

Superhost

The living room features contemporary furnishings, including two patterned armchairs and a cozy sofa. Oversize windows allow natural light to fill the space, while a coffee table and a TV unit add functionality. Lush greenery can be seen through the windows, enhancing the view.