Family-friendly holiday rentals in Hilton Head Island

A bright living area features a light-colored sofa with a navy throw blanket. A glass coffee table stands on a patterned rug, while a tall lamp provides additional lighting. Art prints are displayed on the wall, and a balcony extends into the greenery beyond.

4.91 out of 5 average rating, 128 reviews

Modern Villa, Walk to Beach & Coligny Plaza

Don’t miss this modern-coastal 2 bedroom, 2.5 bath villa right in the heart of Hilton Head, making it the ultimate beach getaway! Walk into an open concept, 2-story villa with a balcony overlooking lush palmetto trees. Cool off and relax in one of the 2 on-site swimming pools. Just a 7 minute walk to the beach and newly developed Lowcountry Celebration Park & Playground. Also a 10 minute walk to Coligny Plaza’s shops and restaurants! The possibilities are endless during your time on the island.

4.98 out of 5 average rating, 163 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

A private balcony overlooks a pool surrounded by lounge chairs and lush greenery. The ocean is visible in the distance, framed by tall trees under a clear blue sky. The space includes a small round table with two chairs.

4.9 out of 5 average rating, 173 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

Welcome to Ocean Pearl Villa. Sit back, relax and listen to the crashing of the waves, while relaxing on your private balcony of our two bedroom, two bath beautiful oceanfront condo. Ocean Pearl is located in Beachwood Place, a 24 unit gated private complex, on Hilton Heads finest South Forest Beach & only 3 minute walk to Coligny Plaza, the heart of Hilton Head's restaurants, Shopping & family activities. You will enjoy the wonderful accommodations and spectacular views at 2H Beachwood Place.

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, 117 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, 354 reviews

Oceanfront KING BED 65"TV Beach Bar Pickleball GYM

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

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, 223 reviews

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

Ready for a beach vacation with a side of golf, pickleball and biking? Welcome to our newly renovated 1st floor villa in Fiddler's Cove. STR Permit# 24587. Our villa is a 6-7 minute walk to Folly Field beach with private beach access. THE best sunrises, just a few minutes away. Surrounded by world class golf courses and fantastic restaurants. Onsite amenities include 2 pools, a hot tub, racquetball, pickleball, tennis and gym. Pools open from March 1 - October 31 and hot tub open year round.

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, 217 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, 119 reviews

Apartment 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.

Superhost

4.8 out of 5 average rating, 179 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

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, 185 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

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, 109 reviews

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

Why you’ll love this space: Fully renovated with high‑end appliances Indoor heated pool & hot tub Outdoor pool, renovated 2025 (Open April 1 - October 31) Tennis - & pickleball courts Approx 5 minute walk to beach; 10 minute walk to Coligny 320 Mbps Wi‑Fi with dedicated workspace Chef’s kitchen, washer/dryer, cypress ceilings Marble walk‑in showers & electric fireplaces Beach gear included (towels, chairs, wagon, toys) STR Permit No. 040546

Villa in Hilton Head Island

A comfortable seating area includes a cozy gray sofa with patterned throw pillows. A bamboo coffee table sits in the center, surrounded by natural light from sliding glass doors leading to a balcony. Vibrant green plants add a touch of nature to the space.

4.96 out of 5 average rating, 213 reviews

Private Beach on Sound | 3 Pools/Spa | Free Tennis

Make the most of beachfront living at this sunny retreat. Our community is closer to the water than any other resort on the island. Pack the cooler and take a short stroll to the beach. Sea’ la Vie is a ground-floor (no stairs) unique escape destination with top-of-the-line comforts of any 5-star rental or hotel. Our villa has been renovated from top to bottom.

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

Apartment in Palmetto Dunes

A serene beach scene captured at sunset, displaying a gradient of warm colors in the sky. Gentle waves reflect the hues of orange and purple as they meet the shore, while wispy clouds add texture to the sunset backdrop.

4.94 out of 5 average rating, 147 reviews

Beach resort, pools, tennis, pickle ball, tiki bar

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, 176 reviews

After Dune Delight | Spacious Condo, Full Kitchen

The living area is furnished with two navy blue sofas adorned with ocean-themed pillows. A glass-top coffee table is situated in front, complemented by two table lamps. Light filters in through the nearby windows, enhancing the serene decor.

4.94 out of 5 average rating, 289 reviews

3BD/2BA condo - Private beach access & 3 pools!

The dining area features a wooden table surrounded by black chairs, with a light fixture above. A view of the living space is visible, showcasing a cozy seating arrangement and a sliding glass door leading to a balcony. Decor and greenery soften the room's ambiance.

4.92 out of 5 average rating, 104 reviews

Entire Condo in Fiddlers Cove

A pristine pool area is surrounded by lush greenery, featuring a spacious pool and a relaxing spa. Poolside seating includes turquoise chairs and an umbrella. A dining table with outdoor chairs is situated nearby, all on a textured stone patio.

4.97 out of 5 average rating, 114 reviews

Private pool/spa : pool heat available : Kg master

Superhost

A stylish living space features a dark leather sofa with a colorful throw and pillows. A painting of a sailboat adorns the wall. The kitchen area showcases granite countertops, bar stools, and stainless steel appliances, enhancing the functional and modern design.

Apartment in Palmetto Dunes

4.78 out of 5 average rating, 314 reviews

BEAUTIFUL CONDO IN HHR, RENOVATED

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

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, 148 reviews

Lovely family Villa Close to Beach

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 105 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

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, 112 reviews

6 BR, Sleeps 26, Beach Time

4.98 out of 5 average rating, 118 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 Sea Pines

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

A charming beach cottage is framed by mature trees and lush landscaping. A pathway of gravel leads to the entrance, featuring a well-maintained lawn. An American flag is displayed prominently, enhancing the welcoming atmosphere of the exterior.

4.98 out of 5 average rating, 64 reviews

80 Steps to Private Beach Access • Walk to Coligny

Apartment in Palmetto Dunes

An inviting open-concept living area features a dining table set for four, complemented by a soft rug beneath. A modern kitchen is visible in the background, with sleek cabinetry and appliances, while a comfortable seating area showcases a leather sofa and glass coffee table, illuminated by ceiling fans.

5 out of 5 average rating, 29 reviews

Luxurious, Dog Friendly Ground Fl Villa Fazio Golf

4.91 out of 5 average rating, 136 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!

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, 395 reviews

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

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, 193 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Family-friendly home rentals with a pool

An open-concept living area features a comfortable sofa and a cozy blue armchair, with large sliding glass doors providing natural light and views of the balcony. A wall-mounted TV and a bar height table with stools complement the space, which is enhanced by a ceiling fan.

4.84 out of 5 average rating, 111 reviews

1st Floor Ocean View Closest Condo to Pool & Beach

Flat in Hilton Head Island

5 out of 5 average rating, 8 reviews

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

4.98 out of 5 average rating, 60 reviews

Oceanview King Villa + 4th July + Steps to Sand

5 out of 5 average rating, 18 reviews

Home in Sea Pines

Modern Home ~ Golf Course Views ~ .8 Mile to Beach

Superhost

A comfortable living area is presented with a cozy sofa and armchairs, accentuated by natural light from the sliding glass doors. A dining table with four chairs is positioned nearby, while a stylish lamp provides additional lighting, enhancing the inviting atmosphere of the space.

4.85 out of 5 average rating, 163 reviews

Cozy upgraded Villa ! 10 min walk to the Beach

4.93 out of 5 average rating, 27 reviews

Brand New Lux Condo - Ocean View! Steps to Beach!

4.95 out of 5 average rating, 21 reviews

Steps to Beach, Water Views, 3 Pools & Hot Tub

The shoreline features a wide expanse of soft sand, with gentle waves lapping at the water's edge. Several beachgoers are seen walking along the coast, while beach umbrellas provide shade to those sitting nearby. Tall grass frames the scene, enhancing the natural beauty.