Family-friendly holiday rentals in Hilton Head Island

4.99 out of 5 average rating, 147 reviews

Home in Sea Pines

“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops

Privately-owned 2000 SF one-level home sits on a wooded corner lot conveniently located inside the entrance of Sea Pines Resort. This 3 BR, 2BA home was extensively renovated in August 2020, with inviting French-inspired coastal decor for a relaxing cozy feel. "Sea La Vie" chalet is within walking distance to grocery stores, shops, and restaurants. A short drive or bike ride takes you to the private Beach Club, housing oceanfront dining and bar, upscale facilities, and wide beaches. Bienvenue!

A tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.

4.97 out of 5 average rating, 303 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 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.

4.98 out of 5 average rating, 104 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

Welcome to Governor's Quarters- your Luxury Hilton Head Getaway Stay Lowcountry in this stately-designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from the SeaPines Beach Club and HarbourTown Golf Links and the heated community pool! Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, HarbourTown Lighthouse, & most importantly- the beach!

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.

4.97 out of 5 average rating, 194 reviews

KING BED Luxury! 65"TV + Beach Bar FREE Pickleball

✨Airbnb Top 5% Guest Favorite✨ Oceanfront Building BIG Ocean View from Balcony Steps to Beach Bar & Pool FREE Gym, Pickleball Tennis Volleyball & More! 100% NEW HGTV Designer Renovation! KING BED 75" & 65" SmartTVs Beach Chairs, Boogie Boards, Ice Chest & More Marble Kitchen/Spa Bath Top Floor WiFi 557 Mbps Elevator RESORT: No Resort Fees 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

4.92 out of 5 average rating, 115 reviews

BEACH PATH At Hilton Head Beach and Tennis Resort

🏖🏖🏖 Book your Summer trip with us!!!! Experience the ultimate beach getaway at our charming villa located within the gated Hilton Head Beach and Tennis. This oceanfront property boasts the largest oceanfront pool on the island, beach volley ball , tennis courts, pickle ball, bike rentals, a playground, grill/picnic area and three delightful restaurants. Nestled-mid island, our villa is conventiently located two miles from Shelter Cove/Palmetto Dunes. Trolley pickup onsite.

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, 355 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, 122 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 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, 98 reviews

Jim's Chic Direct Oceanfront 2BR Villa

Lovely 4th floor villa with a breathtaking, unobstructed ocean view from the living room and master bedroom. Two bedroom suites, each with separate baths. Fully appointed kitchen - granite countertops, updated cabinets, and stainless steel appliances. Walk to all of the amazing shops & restaurants of Coligny Plaza and the brand-new Celebration Park. Jim Says: “I personally stay in each of my units to ensure they are maintained to my highest level of expectations.”

4.95 out of 5 average rating, 137 reviews

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!

5 out of 5 average rating, 116 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.

Apartment in Palmetto Dunes

4.96 out of 5 average rating, 106 reviews

Oceanside Resort - Private Beach Access - 3 Pools

"We absolutely loved our stay! The location was perfect and the host was extremely responsive. This condo is perfect for families. So much to do!" —Katelyn, Mar 2026 ⭐⭐⭐⭐⭐ Welcome to Azure Waves HHI! We are an upscale & fully stocked 2BR/2BA Villa in Building 3 at Hilton Head Resort — Enjoy our 3 Pools, seasonal restaurants, and private boardwalk to Singleton Beach — central to everything on island!

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 spacious outdoor pool reflects sunlight against a backdrop of a resort complex. Lounge chairs are arranged around the pool, with shaded umbrellas positioned throughout. The building's balconies are visible, adding to the inviting atmosphere of the area.

4.91 out of 5 average rating, 314 reviews

Turtle Tracks, Hilton Head Island, SC

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, 129 reviews

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

Superhost

4.8 out of 5 average rating, 178 reviews

Beach Front Villa Oak Tree Lined Views to Water

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, 111 reviews

Private pool/spa : pool heat available : Kg master

Apartment in Palmetto Dunes

A private balcony features comfortable seating with decorative cushions and a small round table. The view showcases a serene landscape of marshland and trees under a colorful sky at sunrise, providing an opportunity for tranquil outdoor relaxation.

4.85 out of 5 average rating, 120 reviews

Stunning Ocean & Coastal Views | Resort Perks!

Superhost

A cozy living area is showcased, featuring a light beige sofa with blue accent pillows and a coffee table displaying colorful magazines. A kitchenette is visible to the left, with white cabinetry and essential appliances. Artwork hangs on the wall, adding a subtle touch to the serene space.

4.88 out of 5 average rating, 161 reviews

Hip Nautic | Pickleball, Indoor Pool & Jacuzzi

Apartment in Palmetto Dunes

A calm bedroom features a spacious bed with a pink patterned quilt, complemented by a decorative beach-themed sign above. Two white closet doors are visible along one wall, while a bedside table holds a lamp. Coastal decor accents enhance the serene atmosphere.

4.9 out of 5 average rating, 268 reviews

HHI. Easy Direct Beach Access. 3 pools- 1 indoor.

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.

4.89 out of 5 average rating, 207 reviews

Hilton Head Hidden Gem

Family- and pet-friendly home rentals

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, 131 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

4.92 out of 5 average rating, 134 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!

4.84 out of 5 average rating, 264 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, 394 reviews

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

Guest house in Hilton Head Island

4.92 out of 5 average rating, 289 reviews

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

5 out of 5 average rating, 9 reviews

Charming Pet-Friendly Beach Home

4.98 out of 5 average rating, 94 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

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, 190 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 37 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

A scenic view is presented from the balcony, showcasing a coastal landscape with sprawling greenery and a sandy beach in the distance. The sky is clear with soft clouds, enhancing the tranquil atmosphere of the surroundings.

4.92 out of 5 average rating, 203 reviews

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

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, 21 reviews

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

The outdoor area features a private pool surrounded by palm trees, with a spacious deck. Comfortable loungers and umbrellas are arranged nearby. Two inflatable swan floats rest on the water's surface, adding a playful touch to the serene setting.

4.94 out of 5 average rating, 52 reviews

5BR Private Pool+Hot Tub+Sauna, 400 Steps to Beach

A modern kitchen features white cabinetry and stainless steel appliances. A light blue tiled backsplash provides a lively contrast. A round dining table set for four is positioned next to a window that allows natural light to fill the space.

4.96 out of 5 average rating, 146 reviews

Heron Hideaway: lovely updated near-beach 2bd/2ba

Superhost

Villa in Hilton Head Island

4.77 out of 5 average rating, 31 reviews

Beachside Bliss Villa with Pools & Tennis

4.99 out of 5 average rating, 105 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.

Apartment in Shipyard

Hilton Head Island VILLA: STEPS 2 Beach & Coligny!

A large home is set within a lush landscape, featuring a spacious deck with seating and a private pool. Lounge chairs are placed nearby, and a hot tub is visible on the stone patio. Tall trees create a serene atmosphere around the property.