Family-friendly holiday rentals in Hilton Head Island

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, 316 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, 278 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 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, 105 reviews

Luxe Hilton Head Beach Villa w/ Pool Views

Escape to our beautiful beach getaway where you are just a short walking distance to a beautiful natural beach. Our completely restored condo is designed with the perfect blend of luxury and relaxation to enjoy your time in Hilton Head. Our spacious and open floor plan creates a bright and an inviting atmosphere that is perfect for lounging with loved ones and friends. Our bedrooms will give you a perfect night of rest and relaxation while each bathroom provides the perfect spa like experience

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 bright kitchen and dining area is featured, showcasing light wooden cabinetry, stainless steel appliances, and a dining table with four chairs. A large flat-screen TV is mounted on the wall, and tasteful decor adds a cozy touch to the space. Natural light fills the room.

4.96 out of 5 average rating, 114 reviews

Beach Front Resort - Ocean View King Bed

OCEAN VIEW-Amazing View-Beachfront 3 MINUTE WALK to the ocean Beachfront condo- Hilton Head Island Beach and Tennis Resort. - Hilton Head is the # 1 rated island by Conde Nast. A tropical landscape- miles of beaches, bike trails, restaurants, boating, fishing, and golf galore. Sleeps 4- 1 KING BED w/bunks in the same room Bunks are NOT twin-size; they are kid-size. Beachfront RESORT, private beach, three restaurants, beachfront pool, Tennis/Pickleball, fitness center & bike rental.

Flat in Hilton Head Island

A comfortable living area features a beige sofa and a cozy chair, complemented by a decorative ottoman. Natural light illuminates the space from sliding glass doors leading to a patio, while serene artwork with ocean themes adorns the wall.

4.81 out of 5 average rating, 154 reviews

1st Floor Beach-Side Villa Resort

Welcome to our beautiful Hilton Head villa! This is a 2 bedroom, 2 bathroom 1st-floor villa in a quiet gated community located within a 5-minute walk from a beautiful beach with a private entrance. Parking for the villa is steps from the door, with shops & restaurants nearby. Perfect for family vacations, golf, and business trips. The gated community has 10 tennis courts, 2 large outdoor swimming pools, a hot tub, racquetball courts, fitness centers & playground. $100 late checkout fee

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, 187 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

Guest house 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, 227 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

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, 401 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 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, 318 reviews

Oceanfront Luxury KING BED 65"TV Pickleball Tennis

PANORAMIC OCEANFRONT VIEWS! Beachfront Balcony ✨Top 5% of Airbnb✨ Beachfront Pool, Bar & Grille FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More HGTV Decorator Renovation KING BED (2) 65" SmartTVs Spa Bath w/Walk-in Shower Expanded Bedroom w/Blackout Sleeping Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More 4 Boardwalks 3 Restaurants Sports Bar Bike Rentals on Site Gated 24/7 Security Island Seasonal Trolley Stop Bradley Beach

4.97 out of 5 average rating, 792 reviews

A welcoming living area features a light-colored sofa adorned with decorative pillows. A round coffee table sits on a textured area rug. A large mirror and a potted plant enhance the space, while natural light enters through the door opposite the seating.

Guest house in Bluffton

Bluffton's Tropical Carriage House Getaway

Embrace the inviting atmosphere of this detached garage apartment. The guesthouse features an open-concept living/*kitchenette/sleeping area, a tropical design, a private entry, a luxury king mattress and blackout window treatments. This southern style hood offers ample sidewalks, ponds for fishing, a playground, and a park. Quaint Old Town Bluffton is a 3 minute drive or 20 minute walk to a number of shops and restaurants. Permit # STR21-00119

A serene beach scene features a boardwalk leading to the water, surrounded by soft sand and lush greenery. The sky is expansive, showcasing soft clouds merging with blue hues. The shoreline is visible in the distance, offering a peaceful atmosphere.

4.98 out of 5 average rating, 131 reviews

Beach condo with pool and stunning nature views

Your peaceful and stylish condo is on Hilton Head’s hidden gem beach, with nature views, lush landscaping, 3 pools, a hot tub, and tennis. This newly remodeled 2-bed/2-bath unit features lagoon and sea views, a screened-in sunroom, new LG appliances, quartz counters, a stocked kitchen, in-unit laundry, 65" TV in the living room, 58"/55" TVs in bedrooms, beach gear (cart, umbrellas, toys), 400 MB Internet—and no cleaning fee!

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

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

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, 107 reviews

Ocean Views at Villamare, Steps to the 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.

4.99 out of 5 average rating, 204 reviews

1st flr, Pools, Tennis, Pickleball & Beach Access

A modern kitchen is illustrated with granite countertops and sleek cabinetry. Stainless steel appliances, including a microwave and oven, are visible. A large island with seating for three complements the space, which transitions into a cozy dining area beyond, illuminated by overhead lighting.

4.94 out of 5 average rating, 195 reviews

Coastal Chic & Tranquil Beach on Hilton Head!

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 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, 138 reviews

Lovely family Villa Close to Beach

Apartment in Palmetto Dunes

A wooden boardwalk stretches over a marsh, leading towards a scenic view. Lush greenery flanks either side, while a detailed sign provides information about the area. Soft clouds float in a bright blue sky, enhancing the natural beauty of the surroundings.

4.89 out of 5 average rating, 119 reviews

Stylish 2BD/2BA beach villa at Hilton Head Resort

A sun-filled sitting area features a light-colored sofa and accent chairs arranged around a rectangular table. Two round mirrors are mounted on the wall, enhancing the space. Sheer white curtains frame the windows, allowing natural light to illuminate the room.

4.94 out of 5 average rating, 161 reviews

Secluded 1st Floor ~ 2 Bed/2 Bath Beach Getaway

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

Townhouse in Hilton Head Island

A comfortable living area features light-colored sofas and a patterned armchair, complemented by a coffee table. Large sliding doors open to a patio with greenery visible outside. Decor includes calming art pieces and a ceiling fan, enhancing the relaxed ambiance of the space.

4.8 out of 5 average rating, 158 reviews

Luxury Villa @ Great Price, Walk 2 Beach/Coligny

4.8 out of 5 average rating, 103 reviews

A cozy living area is presented with a plush green sofa adorned with colorful pillows. A light-toned coffee table rests on a vibrant area rug. Natural light filters through sheer curtains, illuminating the space, which features a potted plant and sliding glass doors leading to an outdoor area.

Apartment in Sea Pines

Family/Couples Condo Retreat - Walk to Beach/Shops

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, 174 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

4.96 out of 5 average rating, 112 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

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.

4.81 out of 5 average rating, 195 reviews

Peace in Paradise on island-pets welcome!

Family-friendly home rentals with a pool

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, 194 reviews

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

5 out of 5 average rating, 106 reviews

A modern kitchen features a central island with a white marble countertop and two woven bar stools. Stainless steel appliances are visible, along with a stylish herringbone backsplash. Natural light highlights the clean lines and organized layout of the space.

Apartment in Sea Pines

5 Star Location! Pool, Walk to Shops/Dining

4.96 out of 5 average rating, 313 reviews

Ocean & Marsh View KING BED 65"TV Bar Pickleball!

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.

4.9 out of 5 average rating, 223 reviews

Oceanside Beach Retreat

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

Villa in Hilton Head Island

A cozy living area showcases two comfortable gray sofas arranged around a wooden coffee table. A dining space with tall chairs is visible near a fully equipped kitchen. Large glass doors open to a private patio featuring outdoor seating and a red umbrella, providing a view of greenery.

4.92 out of 5 average rating, 101 reviews

Escape at Seascape Villas, quiet beach getaway

A cozy living area features a green sofa adorned with patterned cushions, accompanied by two stylish armchairs. A wooden coffee table sits at the center, with decorative elements including a bowl. Artistic nature-themed prints are displayed on the walls, and natural light fills the space through sliding glass doors.

4.89 out of 5 average rating, 122 reviews

Sunny Treetop Getaway w/ tennis and pickleball