Family-friendly holiday rentals in Hilton Head Island

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, 101 reviews

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

Featured in the August 2022 issue of Cottages and Bungalows magazine, this beautifully remodeled 3/2 beach bungalow is nestled in a charming neighborhood within walking distance to Folly Field beach. Enjoy a cup of coffee on the back porch in the morning, relax in the 6 person hot tub after an afternoon round of golf on the many courses nearby or sit by the fire pit and watch the stars at night. 8 Min walk to Folly Field Beach 2 Min walk to Adventure cove mini golf 6 Min Drive to golf & Tennis

A newly constructed beach house is shown from the front, featuring a light blue exterior and a welcoming porch. Palm trees frame the scene, complemented by manicured landscaping. A driveway leads to a two-car garage beneath the home, creating a spacious entryway.

4.99 out of 5 average rating, 83 reviews

Beach House, Elevator, Sleeps 12

Stroll just a few steps from Fish Haul Beach to discover our haven of relaxation.This newly built beach house boasts 3 bedrooms and 2.5 baths complete with complimentary linens and bath towel sets.Enjoy a fully equipped kitchen, ample dining space,and 2 expansive balconies to soak in the coastal ambiance.Enhance your beach stay with included amenities such as boogie boards,backpack beach chairs and wagons.We've anticipated every need and are dedicated to ensuring your stay exceeds expectations!

4.95 out of 5 average rating, 132 reviews

Big OceanView 65TV Beach Bar Pickleball Tennis Gym

✨ Top Airbnb Guest Favorite ✨ Big Ocean View from Living Room & Balcony! Oceanfront Building Steps to Beach, Pool, Tiki Bar & Grill FREE: Pickleball, Tennis, Gym, Volleyball Queen Bed | Queen Sofa | 2 Bunks Beach Chairs, Boogie Boards & More! 65" SmartTV Fast WiFi 652 mbps HGTV Decorator Updated Top Floor w/Elevator Couples/Small Families RESORT: Oceanfront Pool, Bar & Grill 4 Beach Boardwalks Sports Bar w/Pool Table Bike Rentals Big Shady Playground 2nd pool 3 BBQ Areas Gated 24/7 Security

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, 102 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, 119 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, 358 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

4.86 out of 5 average rating, 118 reviews

An outdoor area features a heated private pool surrounded by a spacious patio and lounge chairs. The home, with updated siding, has a shaded seating area and a barbecue grill. Lush greenery and colorful flowers enhance the tranquil ambiance.

Home in Palmetto Dunes

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.

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, 143 reviews

Beach condo with pool and stunning nature views

Warm, modern, and designed with character—this newly remodeled 2-bed/2-bath is the closest condo to Hilton Head's hidden gem beach, with lagoon and sound views. King bed in the primary, twin beds in the kids' room: screened-in sunroom, 3 pools, hot tub, tennis. Fully stocked kitchen with a guest-favorite coffee bar, restocked fresh each stay. In-unit laundry, big-screen TVs in every room, all the beach gear you need (cart, chairs, boards, toys, and more), 400 MB Internet—no cleaning fee!

A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.

4.96 out of 5 average rating, 219 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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**

5 out of 5 average rating, 122 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.

5 out of 5 average rating, 5 reviews

Guesthouse in Bluffton

Cozy Carriage House Under Oaks | Old Town Bluffton

nook - /nʊk/ – a secluded or sheltered place or part. We welcome you to The Nook, a peaceful escape nestled beneath centuries-old oak trees and located steps away from the vibrant core of the Old Town Bluffton Historic District. Spend your days strolling tree-lined streets, dining at some of the Lowcountry’s best restaurants, and enjoying scenic parks overlooking the beautiful May River. Begin and end your day at your restful, coastal retreat.

Villa in Hilton Head Island

The image showcases a heated pool surrounded by palm trees and lounge chairs. Umbrellas provide shade over some seating areas. A white fence encloses the pool area, with lush greenery and ocean views in the background, creating a tranquil outdoor environment.

4.93 out of 5 average rating, 120 reviews

💎Direct Oceanfront Villa - Heated Pool Ocean View

Welcome to the Ocean Gem! Relax and listen to the crashing waves on your private balcony of our newly renovated, newly furnished, direct oceanfront, one bedroom, one bathroom, beautiful beach villa. Ocean Gem is located in Ocean Dunes complex, a private gated community, on South Forest Beach and only steps from the popular Coligny Plaza. You will enjoy the wonderful accommodations, heated pool, picnic area and spectacular views! Thank you

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

4.93 out of 5 average rating, 135 reviews

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.

Condo in Palmetto Dunes

Sea Gem - A Cozy Hilton Head Beach Escape

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 1404, Right on the Beach!

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, 225 reviews

Few mins walk to beach 1st flr pools hot tub pball

Superhost

4.8 out of 5 average rating, 181 reviews

Beach Front Villa Oak Tree Lined Views to Water

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, 188 reviews

Beach condo in gated resort w/ tons of amenities!

4.81 out of 5 average rating, 273 reviews

Condo in Palmetto Dunes

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

4.96 out of 5 average rating, 136 reviews

Remodeled Villa Minutes to Beach, Pools, Bar Grill

Villa in Hilton Head Island

An open dining and living area showcases a large dining table with upholstered chairs beneath a stylish chandelier. Recessed lighting highlights the wood-paneled ceiling, while large windows offer views of the greenery outside, enhancing the bright and airy atmosphere of the space.

4.99 out of 5 average rating, 113 reviews

Walk to Beach, Indoor Pool, King Bed, Hot Tub!

Family- and pet-friendly home rentals

Luxe

Villa in Sea Pines

5 out of 5 average rating, 11 reviews

100 Fairway Lane, Sea Pines: A Luxury Villa Stay

4.91 out of 5 average rating, 74 reviews

Treehouse in Sea Pines

CoCo's Island Treehouse

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

4.98 out of 5 average rating, 107 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

4.85 out of 5 average rating, 151 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

Superhost

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.

Cottage in Hilton Head Island

4.83 out of 5 average rating, 102 reviews

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

4.91 out of 5 average rating, 139 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!

4.96 out of 5 average rating, 182 reviews

Perfect spot for a great getaway

Family-friendly home rentals with a pool

5 out of 5 average rating, 23 reviews

Apartment in Sea Pines

Harbour Town Marina Studio | Walk to Lighthouse

Superhost

Home in Palmetto Dunes

5 out of 5 average rating, 3 reviews

Luxury Dunes Paradise - Private Pool

4.93 out of 5 average rating, 40 reviews

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.

Home in Sea Pines

Starfish Beach House with Pool and Bikes

Apartment in Hilton Head Island

5 out of 5 average rating, 9 reviews

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

5 out of 5 average rating, 6 reviews

Home in Sea Pines

10 Pender Lane-Sea Pines Home

5 out of 5 average rating, 22 reviews

Oceanfront Hilton Head Villa | Salt & Sunrise

5 out of 5 average rating, 7 reviews

Home in Shipyard

Coastal Fairways