Family-friendly holiday rentals in Hilton Head Island

A spacious bedroom features a comfortable bed dressed in a patterned coverlet, accompanied by crisp white towels. Soft lighting is provided by bedside lamps. Decorative accents include a branch art piece on the wall and a small shelf displaying coastal-themed items. Natural light filters through a window with sheer curtains.

4.95 out of 5 average rating, 221 reviews

$59/nt -Nov 17-21, 24-27 ~CLEAN ~KING Bed~Sleeps 7

Fully Furnished, Renovated Non-Smoking Villa sleeps 7 - King bed in Master, 2 Single beds in Guest Room, Leather Queen Sofa Bed & Rollaway Bed. Built-in Bar, Fully-equipped Kitchen w/ small appliances. Beach Chairs, toys, games, cards. Flat Screen HDTV w/ hundreds of channels, DVD, Free Wi-Fi. Overhead Lighting & Ceiling fans in bdrms, extra blankets & pillows. Restaurants, Tennis, 2 Pools. Sip cold drinks on the wide sandy beach & watch Amazing Sunrises & Sunsets. Relax, You're in Paradise

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, 319 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! 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!

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, 279 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!

A decorative shelving unit displays an assortment of illuminated lighthouses in various colors. The vibrant lighting creates a calming ambiance, highlighting unique designs in each lighthouse. Darker corners contrast with the radiant colors, enhancing the visual appeal of the arrangement.

4.98 out of 5 average rating, 181 reviews

"Beach Time" - a cozy HHI Condo, steps from beach

No price increase. Low cleaning, low gate fees! Check out my beach-skybox-hhi. HHI Beach & Tennis is a beachfront resort with many vacation amenities. Our condo is on first floor of Ocean Villas B, close to the pool and beach activities but far away enough from noise of pool and restaurant. Our condo is 2-3 minutes from the beach. For your health and comfort, we have an air system, ozonizer, AC and dehumidifier. Check out our other condo, beach-skybox-HHI. It has a panoramic view of the beach

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.

4.94 out of 5 average rating, 125 reviews

Desirable Oceanfront Resort*End Unit*Bikes/Chairs

Charming villa with everything you need for the perfect beach getaway- just steps from the sand! Elevated 1st floor, END UNIT offers lots of natural light and ramp for easy access. Situated in desirable C building, closest to beach, pool and Jamaica Joe'z restaurant/ tiki bar. 2 FREE bikes, chairs & beach towels! HHBT Resort provides gated security and countless amenities, including the island's largest oceanfront pool, multiple restaurants/ bars, tennis courts, playgrounds & fitness center.

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.

4.98 out of 5 average rating, 165 reviews

Luxury OceanView KING BED 65"TV Bar Pickleball GYM

✨ Airbnb Top 5% Guest Favorite ✨ Oceanfront Building! BIG Ocean Views Steps to Beach & Poo! 100% NEW HGTV Designer Renovation! KING BED Expanded Bedroom Two 65" SmartTVs Coastal Decor Beach Chairs, Boogie Boards, Ice Chest & More Marble Kitchen & Spa Bath Quiet Top Floor Elevator RESORT: Huge Oceanfront Pool Beachfront Bar & Grille (Misc. Hours) Sports Bar FREE Gym, Pickleball, Tennis Basketball, Volleyball & More Bike Rental Gated 24 Hour Security Free Seasonal Trolley 4 Beach Boardwalks

Apartment in Hilton Head Island

Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.

4.82 out of 5 average rating, 177 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate renovated baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

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.

4.96 out of 5 average rating, 103 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.

Apartment in Palmetto Dunes

The living area features a comfortable gray sofa and an armchair, providing ample seating. A flat-screen TV is mounted on the wall above a wooden console table, accompanied by decorative accents. Soft lighting is provided by a lamp, creating a cozy atmosphere.

4.94 out of 5 average rating, 130 reviews

Gorgeous Hilton Head Beach Condo

Welcome to your dream vacation rental in Hilton Head Island! Nestled in a prime location, this exquisite condo offers the epitome of coastal luxury and relaxation. As you step inside, you're greeted by a newly updated interior adorned with contemporary furnishings, creating a welcoming and comfortable atmosphere for you and your family. The spacious living area is perfect for unwinding after a day at the beach, featuring plush sofas and a flat-screen TV for your entertainment.

A sunlit living space features a navy blue sofa and an elegant dining table surrounded by four chairs. Large sliding glass doors provide access to the oceanfront balcony, where views of the beach and coastal landscape can be seen in the distance.

4.97 out of 5 average rating, 191 reviews

Oceanfront Luxury! KING BED 75"TV Pickleball | BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 5% Home ✨ 100% New Luxury Renovation Oceanfront Balcony HGTV Featured Decorator KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR+Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT Beachfront Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball 2nd Pool Bike Rental Gated w/24 Hour Security Free Trolley Stop Bradley Beach

A stunning sunrise illuminates the ocean, casting a warm golden glow across the water's surface. Rays of sunlight stretch outward, reflecting off the gentle waves. The shoreline is visible, framed by soft grasses, enhancing the tranquil morning scene.

4.99 out of 5 average rating, 166 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, 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! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! 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**

Guesthouse in Hilton Head Island

A combined living and sleeping area features a gray couch with decorative pillows, a small coffee table, and a light-colored area rug. A twin bed with a white quilt and pillows is visible in the background, with large windows draped in yellow curtains allowing natural light to enter.

4.93 out of 5 average rating, 232 reviews

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

Your family will be close to everything when you stay at this centrally-located place. No gate fees or parking fees- right off of 278- central located between Bluffton and HHI under foot of bridge. Farm like experience -family owned 30 years . Quiet . Pet friendly . Beds-two twin -can pull together if wish -one couch(Not a sofa bed) and one mattress under a bed that can be moved out . Property has several buildings , Guest apt is above garage. NOTE: SEE Space info below

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

4.95 out of 5 average rating, 125 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

The open-plan living and dining area is bathed in natural light, featuring a stylish dining table set for six. A comfortable blue sofa invites relaxation, while a patterned area rug adds warmth. The room is complemented by decorative elements, including a lantern and dried floral arrangements.

4.88 out of 5 average rating, 145 reviews

Turtle View Villa

4.88 out of 5 average rating, 175 reviews

Condo in Palmetto Dunes

Renovated - Walk to Beach - 3 Pools - King Bed !

A dining table is set for six with blue plates and clear glasses. The kitchen is visible in the background, featuring white cabinets and major appliances. A light fixture illuminates the space, while a cozy living area is accessible through an open doorway.

4.86 out of 5 average rating, 319 reviews

Gorgeous villa, private beach access, HH Resort

A serene landscape is presented, featuring a tranquil pond surrounded by lush greenery and palm trees. The view extends toward the beach, with well-maintained walkways leading through the gardens. A clear sky with scattered clouds adds to the peaceful ambiance.

4.92 out of 5 average rating, 142 reviews

Exclusive Oceanfront Decorator Decor Spacious Bdrm

Superhost

A wooden boardwalk extends across sandy terrain, leading towards a serene coastal view. Lush green grass is visible on both sides, with a calm ocean horizon meeting a partly cloudy sky above.

Apartment in Hilton Head Island

4.86 out of 5 average rating, 115 reviews

Quiet Life by the Beach

A large, inviting pool area is surrounded by palm trees and lounge chairs. The pool's curvy shape is highlighted by soft lighting, creating a relaxing atmosphere. Adjacent to the pool, a spacious building features expansive windows, enhancing the connection to the outdoor space.

4.95 out of 5 average rating, 120 reviews

Beachside Hilton Head Villa Fully Renovated

Superhost

A spacious kitchen featuring sleek white cabinetry and a large marble island with seating for four. Modern appliances, including a stainless steel refrigerator and oven, are visible, along with a stylish black backsplash that complements the overall design.

4.9 out of 5 average rating, 107 reviews

Luxe Hilton Head Beach Villa w/ Pool Views

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 121 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

Cottage in Hilton Head Island

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.

4.92 out of 5 average rating, 118 reviews

Shipyard! - Private Beach & Golf! Pet Friendly!

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, 176 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

4.95 out of 5 average rating, 114 reviews

The bungalow is nestled among lush greenery and tall trees, surrounded by a natural environment. Palm leaves frame the structure, and a small deck is visible at the front, inviting warmth and privacy in this woodland setting.

Bungalow in Sea Pines

Closest to Beach Path, Screened Porch, 1 dog ok

Home in Hilton Head Island

A two-story house features a light blue exterior with white trim and black shutters, showcasing a spacious driveway. A six-person black golf cart is parked in front, contrasting against the landscaped area with tropical plants and a nearby streetlamp.

4.93 out of 5 average rating, 216 reviews

Enjoy time with family and friends

A spacious bedroom features a large bed adorned with a colorful floral quilt and accented by several plush pillows. A bedside lamp provides soft lighting, while a window offers a view of the outside greenery, contributing to a calm atmosphere.

4.92 out of 5 average rating, 170 reviews

By the Beautiful Sea, 30 Day Discounts available

Superhost

An open-concept living area is visible, featuring a comfortable sofa with a red throw blanket. A wooden dining table with pastel chairs is set for four, while a large screen TV is mounted on the wall. Natural light enters through a sheer curtain-covered window.

4.8 out of 5 average rating, 196 reviews

Peace in Paradise on island-pets welcome!

4.91 out of 5 average rating, 117 reviews

The open living area features new reclining furniture arranged around a coffee table. A flat-screen TV is positioned on a media console against the wall. Light-colored tiles and a patterned area rug enhance the spaciousness, complemented by a ceiling fan and decorative shelving.

Villa in Palmetto Dunes

Walk to the Beach, One Level Villa, COMFY beds

Family-friendly home rentals with a pool

4.78 out of 5 average rating, 207 reviews

BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN

4.95 out of 5 average rating, 97 reviews

HUGE Ocean View 65"TV Pickleball BAR GYM & Tennis!

4.98 out of 5 average rating, 175 reviews

An outdoor dining area is shown, featuring a round table with six ornate metal chairs. A large red umbrella provides shade, and lush greenery and a view of the marina are visible in the background.

Condo in Sea Pines

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

A serene bedroom space features a spacious bed with a light patterned coverlet. A mirror and a closet are visible, while a smart TV is positioned atop a white cabinet. Soft natural light enters the room through a nearby door leading to an adjacent area.

4.93 out of 5 average rating, 215 reviews

Ocean front condo with amazing ocean view!

The living area is furnished with a large sectional sofa and a single armchair, oriented around a flat screen TV mounted on the wall. A wooden coffee table is centered in the space, and natural light enters through the window adorned with sheer white curtains. Decorative wall art and a shelf with various items are present.

4.96 out of 5 average rating, 134 reviews

Newly Renovated: Island Hideaway on Hilton Head

A comfortable living area is featured, furnished with a sectional sofa and accent chair. Natural light pours in from the sliding glass door, which leads to a private balcony. A mounted television and a decorative mirror enhance the space, creating a cozy setting.

4.95 out of 5 average rating, 199 reviews

Hilton Head Beach & Tennis Getaway!

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.

4.89 out of 5 average rating, 148 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐