Family-friendly holiday rentals in Hilton Head Island

4.99 out of 5 average rating, 148 reviews

“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 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, 196 reviews

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

✨Airbnb Top 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- Feb-Nov Sports Bar Bike Rental Gym & Tennis Gated 24/7 Security Free Island Trolley (Apr-Sept) 4 Beach Boardwalks

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 Luxury! KING BED 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 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, 221 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 wooden boardwalk meanders through grassy dunes, leading toward a peaceful beach with gentle waves. The horizon stretches over the calm ocean, while scattered clouds float in a bright blue sky, creating a tranquil scene that invites relaxation.

4.78 out of 5 average rating, 101 reviews

Poolside + Beach + Natural Paradise 3rd Floor

3 Min Walk to beach - Enjoy the privacy of a third-floor condo with the convenience of a resort at this stylish, modern condo in Hilton Head. Recently remodeled, this modern apartment is the perfect holiday getaway for couples or small families. Overlooking the pool and just a short walk to the beach, it’s the ideal location for a relaxing vacation. 3 Min Walk to the beach 3 Min Drive to Hilton Head Distillery 6 Min Drive to Hilton Head Hospital Experience Hilton Head Island With Us Today!

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!

Top-floor 2BR/2BA villa with ocean, marsh & golf views. Enjoy stunning sunrises & sunsets from your balcony. 5-min walk to semi-private beach or take the seasonal shuttle. 1 mile to Shelter Cove's dining, shopping & entertainment. Resort-style community with 3 pools, gym, bike rentals & beach access—perfect for families, couples & girls’ trips! ⭐ Guests Love It! ⭐ ★★★★★ "Kim was SUPER responsive! The view was amazing. The beach was beautiful & uncrowded. My boys & I loved the boardwalk!"

4.98 out of 5 average rating, 161 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

Beach Resort! Luxury Golf & Lagoon View Pickleball

Gated Beach & Golf Resort! ✨Top 5% Airbnb Guest Favorite✨ Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis - across street HGTV Decorator designed Panoramic Golf & Lagoon Views 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 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, 123 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, 437 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 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.”

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, 315 reviews

Turtle Tracks, Hilton Head Island, SC

Flat in Hilton Head Island

A cozy living area is furnished with a large gray sectional sofa and a woven armchair. A round black coffee table sits in front, while a soft lamp provides warm lighting. The walls feature a colorful abstract art piece, enhancing the inviting feel of the space.

4.86 out of 5 average rating, 300 reviews

Cozy 2 Bedroom/2 bath Beach Villa 2124

4.95 out of 5 average rating, 130 reviews

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.

Home in Palmetto Dunes

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

Apartment in Palmetto Dunes

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.

4.94 out of 5 average rating, 120 reviews

Ocean Views at Villamare, Right on the Beach!

Apartment in Palmetto Dunes

4.96 out of 5 average rating, 108 reviews

Oceanside Resort - Private Beach Access - 3 Pools

The living area features a reclining leather sofa and a coffee table made of wood. A flat-screen TV is mounted on the wall, complemented by light teal walls that enhance the airy feel. A chair sits nearby, providing additional seating.

4.94 out of 5 average rating, 124 reviews

HHR Building 1-Heated Outdoor Pool-Walk to Beach

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, 113 reviews

Private pool/spa : pool heat available : Kg master

A dining area features a wooden table set for six, accompanied by white chairs. Natural light flows through the window, illuminating the adjacent modern kitchen with stainless steel appliances and light cabinetry. A comfortable seating area is visible in the background.

4.8 out of 5 average rating, 265 reviews

Pool side condo just steps from beach boardwalk!

Family- and pet-friendly home rentals

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

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.

4.98 out of 5 average rating, 104 reviews

Governor’s Quarters Pet Friendly, Fenced in Yard

Superhost

4.75 out of 5 average rating, 4 reviews

Wren's Nest - 4BR SeaPines Retreat+Backyard Oasis

4.91 out of 5 average rating, 131 reviews

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.

Home in Palmetto Dunes

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, 395 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

Family-friendly home rentals with a pool

5 out of 5 average rating, 6 reviews

MyStay at SeaCrest 2313 | Ocean Views + Pools!

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.

4.95 out of 5 average rating, 37 reviews

Starfish Beach House with Pool and Bikes

Flat in Hilton Head Island

5 out of 5 average rating, 7 reviews

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

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

Cottage in Palmetto Dunes

4.86 out of 5 average rating, 407 reviews

Gypsy Sea Cottage - A Beachside Retreat

4.98 out of 5 average rating, 44 reviews

1st floor, oceanfront, 65" TV, pickleball, 2 pools

Superhost

Villa in Hilton Head Island

4.83 out of 5 average rating, 12 reviews

Fresh & Modern Villa by the Sea Beach Club Getaway