Family-friendly holiday rentals in Hilton Head Island

4.95 out of 5 average rating, 109 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

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!

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, 319 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!

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, 123 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 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, 117 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

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, 378 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, 134 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 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, 452 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.

A light-filled living area features a cozy seating arrangement with a white sofa and a coffee table. The kitchen can be seen in the background, highlighting modern cabinetry and a casual dining setup. Natural textures are present through the woven rug and wood accents.

4.83 out of 5 average rating, 193 reviews

Close to BEACH bar&grill! Sleeps 6, 2 bed 2 bath!

5 minute walk to closest beach(with beach bar). 19 minute walk to Coligny beach! COME STAY at this charming beach-walk community! The pool is at the bottom of the stairs, 3/4 of a mile to Coligny circle with grocery store, shops, and restaurants. “COPPERTONE DAYS” features: 4 twin beds(memory foam), a master bedroom/master bath, laundry room, and a stocked kitchen+ highchair and a crib! We can usually accommodate early arrivals! Short term rental permit#: 029154

4.94 out of 5 average rating, 147 reviews

Spacious Villa in Hilton Head Resort! STR#024945

Spacious two-bedroom/two-bathroom villa includes its own washer and dryer! This updated villa will not disappoint. It's located in Hilton Head Resort with so many amenities: private access to Singleton Beach, two outdoor pools, seasonal onsite grill/bar/store, heated indoor pool, hot tub, kiddy pool, sauna, exercise room, and track. There are also tennis, pickleball, and badminton courts! Bike paths are plenty with many nearby stores, restaurants, and golf courses!

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, 201 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

4.81 out of 5 average rating, 187 reviews

Beach Front Villa Oak Tree Lined Views to Water

3 Min Walk to the Beach - Your personal paradise awaits! Whether you’re visiting for a weekend getaway or a long-term snowbird retreat, this beautiful beachfront villa is sure to please. You’ll stay just steps from the beach and enjoy lagoon views and amenities this quiet gated community offers, including 24-hour security, pools, a sauna, tennis, and more! 3 Min Walk to the Beach 3 Min Drive to Hilton Head Distillery 12 Min Drive to Shelter Cove Harbor

Popular amenities for Hilton Head Island family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.83 out of 5 average rating, 288 reviews

Boardwalk to Beach, Pools, Hot Tub!

4.82 out of 5 average rating, 285 reviews

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

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.

4.94 out of 5 average rating, 146 reviews

Sea Gem - Winter Sunshine by the Sea

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!

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.

4.95 out of 5 average rating, 115 reviews

Lovely Beachside Villa w/ Resort Amenities

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, 157 reviews

Lovely family Villa Close to 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.

4.98 out of 5 average rating, 232 reviews

1st flr villa few mins walk to beach pools & pball

A serene beach scene showcases a wide expanse of sandy shore bordered by gentle waves under a clear blue sky. The shoreline leads toward distant buildings, creating a tranquil atmosphere at the water's edge.

4.87 out of 5 average rating, 145 reviews

Relaxing 2Br/2ba condo on HHI, minutes from beach

Family- and pet-friendly home rentals

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

4.9 out of 5 average rating, 104 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

4.97 out of 5 average rating, 108 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

4.94 out of 5 average rating, 238 reviews

Large home, beach close, pool

4.98 out of 5 average rating, 110 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

4.84 out of 5 average rating, 269 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!

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, 405 reviews

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

4.84 out of 5 average rating, 148 reviews

Home in Palmetto Dunes

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

Family-friendly home rentals with a pool

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, 239 reviews

*New* Easy Breezy at Hilton Head Beach & Tennis

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, 238 reviews

Across from the beach and Coligny Plaza!

The living area features a light-colored sofa and a glass coffee table, with a view of the resort through sliding glass doors. Soft-hued walls complement the decor, while mirrored panels reflect natural light, enhancing the spacious feel. A dining table with seating for four is visible in the background.

4.95 out of 5 average rating, 149 reviews

Desirable Oceanfront Resort*End Unit*Bikes/Chairs

The image displays a large swimming pool surrounded by lounge chairs, with a view of the sandy beach and ocean beyond. The shoreline features umbrellas for shade, while the landscape includes greenery and distant beachgoers enjoying the sun.

4.76 out of 5 average rating, 156 reviews

Relax and Unwind at this Ocean Front Resort

A welcoming living area features a light grey sofa adorned with blue and white accent pillows. A modern kitchen with sleek cabinetry and stainless-steel appliances is visible, complemented by two wicker stools at the counter. Art depicting herons hangs on the wall.

4.85 out of 5 average rating, 186 reviews

HHB&T 3 min walk to the sand

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.

4.97 out of 5 average rating, 167 reviews

Fully Renovated 2 Bedroom Villa - Walk to Beach

Townhouse in Palmetto Dunes

4.96 out of 5 average rating, 105 reviews

Steps to Pool + Private Beach | Baby Gear!

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.