Family-friendly holiday rentals in Hilton Head Island

4.95 out of 5 average rating, 108 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

KitchenIndoor spacesBarbecue

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!

FamilyKitchenNearby

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

Our house is located on the southern end of Hilton Head Island in the North Forest Beach neighborhood. The house is an easy 5 minute walk to Hilton Head's beautiful beach. Heron St offers its own private beach walk. It’s also a 10 minute walk to Coligny Plaza, offering local shopping, restaurants, and a grocery store. The house features a delightful outdoor shower, 2 bicycles and a shed loaded with 2 beach chairs, boogie boards, a frisbee and a surf fishing pole and tackle. STR Permit# 073978

FamilyIndoor spacesPets

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, 122 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.

KitchenIndoor spacesAccuracy

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.

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.

Indoor spacesFamilyLocation

4.95 out of 5 average rating, 146 reviews

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

FamilyIndoor spacesDecor

An aerial view captures a large pool shaped like a star, surrounded by lounge chairs. The pool area is complemented by umbrellas and seating, with a sandy beach and the ocean visible in the background under clear blue skies.

4.9 out of 5 average rating, 238 reviews

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March 2026 and completely redesigned from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa. Wake up to sunrise over the Atlantic, grab coffee on your private balcony, and walk to the beach in under two minutes. Spend the afternoon at Hilton Head’s largest oceanfront pool before ending the day with dinner and live music just steps from your condo. Beach chairs, wagon, pickleball, tennis, free parking, & close to the building's only elevator.

Indoor spacesFamilyHospitality

Townhouse in Palmetto Dunes

Steps to Pool + Private Beach | Baby Gear!

Welcome to Beachwalk Bungalow - a newly renovated coastal beauty in a prime location! Just a 5 minute walk to Shipyard’s private beach, and the community pool is steps from your front door. Unwind with plenty of space to relax: 2 family rooms, a large eat-in kitchen & 2 owner’s suites offer comfort for all. Fire up the gas grill and lounge on the deck with a drink in hand. Traveling with kids? We have tons of free gear for you, including beach chairs, towels, toys, cribs & way more!!

KitchenIndoor spacesBathroom

4.96 out of 5 average rating, 104 reviews

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, 375 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!

Indoor spacesFamilyLaundry

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, 450 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.

Indoor spacesFamilyLong stay

4.9 out of 5 average rating, 102 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

Welcome to 640 Queens Grant, your perfect family getaway on Hilton Head Island! This vibrant 3BR, 2.5BA luxurious villa is professionally decorated, accented with inviting, colorful coastal decor throughout. The villa offers a fully-remodeled kitchen, a spacious and comfortable living area with plenty of ways to relax and unwind. Outside, there is a large, private patio with a gas grill, an outdoor dining set and fast access to five community swimming pools and the beach.

FamilyKitchenWi-Fi

A bright living area features a comfortable sofa and additional seating, including a wicker chair. A coffee table sits on a decorative rug, while large sliding glass doors allow natural light and views of the outdoors. Simple decor adds a relaxed beach ambiance.

4.92 out of 5 average rating, 198 reviews

Stay by the Beach ⛱ Eat & Shop at Coligny plaza!

Park your car and walk to everything! This beautiful 2 bedroom/1.5 bath 2-storey beach villa is perfect for your family vacation, couple's getaway, or remote work location. The location can't be beat. Just across the street from a public beach access path, and a 5-minute walk to all the amenities of Coligny Plaza (70 Shops & Restaurants) and Celebration Park! I also provide beach chairs, umbrella, and beach cart for your convenience during your stay. #021800

Indoor spacesKitchenWalkability

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

4.94 out of 5 average rating, 145 reviews

Condo in Palmetto Dunes

Spacious Villa in Hilton Head Resort! STR#024945

FamilyIndoor spacesNearby

4.97 out of 5 average rating, 117 reviews

Condo in Palmetto Dunes

Oceanside Resort - Private Beach Access - 3 Pools

FamilyIndoor spacesComfort

4.83 out of 5 average rating, 286 reviews

Condo in Palmetto Dunes

Boardwalk to Beach, Pools, Hot Tub!

FamilyKitchenWi-Fi

A pair of flip-flops and a set of brown sandals are placed on the soft, sandy beach. Sparse green grass and plants are visible in the background, complementing the tranquil beach setting.

4.9 out of 5 average rating, 216 reviews

Hilton Head Hidden Gem

KitchenIndoor spacesCleanliness

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.

4.98 out of 5 average rating, 232 reviews

Reno’d 1st flr walk to beach pools hot tub & pball

FamilyKitchenBathroom

4.84 out of 5 average rating, 268 reviews

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

Private Beach Access-Pet Friendly-Hot Tub!

FamilyKitchenSleep quality

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, 155 reviews

Lovely family Villa Close to Beach

FamilyKitchenHospitality

4.82 out of 5 average rating, 221 reviews

Ground Floor Unit, Steps away from the Beach!

KitchenIndoor spacesSleep quality

Family- and pet-friendly home rentals

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

KitchenIndoor spacesAmenities

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, 404 reviews

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

Indoor spacesFamilyNearby

4.85 out of 5 average rating, 155 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

KitchenFamilyLong stay

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.

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

Indoor spacesFamilyBeach

4.84 out of 5 average rating, 109 reviews

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!

KitchenFamilyComfort

Superhost

Home in Palmetto Dunes

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

KitchenIndoor spacesBathroom

4.84 out of 5 average rating, 147 reviews

4.98 out of 5 average rating, 105 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

FamilyKitchenDecor

4.91 out of 5 average rating, 221 reviews

A spacious living area is presented with large windows offering views of the surrounding greenery. Two armchairs and a sectional sofa provide comfortable seating, while a circular coffee table sits on a patterned rug. Soft lighting is provided by floor lamps, enhancing the inviting atmosphere.

Townhouse in Shipyard

Stylish Tennis-Golf- Beach Retreat-Renovated!

Indoor spacesKitchenBathroom

Family-friendly home rentals with a pool

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

KitchenIndoor spacesQuiet

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, 316 reviews

Ocean View! Remodeled! Steps to beach/Pool/Bar

Indoor spacesFamilyView

A shaded balcony is furnished with two woven chairs and a small table, complemented by a decorative area rug. Lush greenery is visible beyond the railing, providing a natural backdrop, while large windows allow for ample light to fill the space.

4.98 out of 5 average rating, 134 reviews

Cozy beach house w/Private Heated Pool near park

KitchenFamilyComfort

A thatched-roof pavilion offers shaded seating, featuring white patio furniture arranged around circular tables. The sun rises in the background, casting a warm glow, while a sandy beach and volleyball court are visible nearby, creating a welcoming space for relaxation and social gatherings.

4.9 out of 5 average rating, 236 reviews

Across from the beach and Coligny Plaza!

KitchenFamilyGetting around

Apartment in Hilton Head Island

The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven. White cabinetry with glass accents showcases dishware. A marble countertop provides ample workspace, and recessed lighting brightens the room, enhancing its inviting ambiance.

Fully Renovated 2 Bedroom Villa - Walk to Beach

KitchenIndoor spacesValue

4.97 out of 5 average rating, 167 reviews

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, 142 reviews

Oceanview Luxury! King Bed 75"TV Pickleball & Bar

KitchenFamilyOutdoor spaces

4.98 out of 5 average rating, 119 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!

Indoor spacesKitchenParking

A modern kitchen area is showcased with stainless steel appliances and white cabinetry, complemented by a light wooden countertop. A cozy seating area is indicated by a curved sofa, while a large television sits on a wooden stand, enhancing the welcoming ambiance.