Family-friendly holiday rentals in Hilton Head Island

4.98 out of 5 average rating, 123 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.

Condo in Shipyard

Hilton Head Island VILLA: STEPS 2 Beach & Coligny!

Welcome to The Hilton Head Islander! A cozy retreat meticulously maintained for up to 6 guests. Situated in North Forest Beach, it's near Hilton Head's treasures beaches, bars, shops, and eateries. Enjoy a 6-min walk to the beach and the beautiful Celebration Park and 2-min walk to Coligny Plaza! Essentials like toiletries, Kcups, beach gear, & more are provided. While cozy with one bathroom, your comfort is guaranteed. Relax by the onsite pool and enjoy the spectacular beaches. Enjoy your stay!

4.95 out of 5 average rating, 109 reviews

Steps to Beach, Pool, 5BR, Great Location

Make this brand new (2023) custom built home, Sur La Mer at Burkes Beach, your vacation destination! This 5 bedroom home is a guaranteed picture perfect destination for your family or group of up to 14 people and features a heated private pool* and a short walk to the beach. Sur Le Mer is located just steps from beach access and right next to Chaplin Community Park (basketball, playground, tennis, baseball diamond and open field). It's also short drive to local restaurants, bars, grocery store

A welcoming living area is presented, featuring a comfortable sofa and a round dining table with two chairs. A wall-mounted television is visible. Natural light floods in through sliding glass doors, offering a view of palm trees and outdoor seating.

5.0 out of 5 average rating, 114 reviews

The Lookout - A Modern Beach Retreat (Oceanfront)

Welcome to The Lookout! The moment you step into this villa you will be greeted by an open floor plan, a fully stocked kitchen, & every amenity that you'll need for your stay. Take a seat on one of the high top adirondack chairs & enjoy your favorite beverage while overlooking the most popular beaches on the island. Truly - every square inch of this unit has been meticulously utilized to give you an unforgettable vacation. We look forward to hosting you at Seaside Villa's premier luxury villa!

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.

4.98 out of 5 average rating, 322 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 shaded balcony is furnished with two woven chairs and a small table, complemented by a decorative area rug. Lush greenery is visible beyond the railing, providing a natural backdrop, while large windows allow for ample light to fill the space.

4.98 out of 5 average rating, 136 reviews

Cozy beach house w/Private Heated Pool near park

Short walk to Singleton beach or Burkes beach. This oversized 4 bedroom 4 ensuite is the perfect retreat close to everything the Island has to offer. The home features a screened in pool with TV and adjacent ping pong table. The open concept living space is perfect for entertaining with access to a large porch and grill. The property is steps away from Chaplin Park that hosts Tennis, Playground, Soccer, Baseball, Basketball, Trails and Fields for the kids to play. Sleeps 12. STR# 034482

A welcoming living area is furnished with a dark sofa and a light-colored armchair. A wooden coffee table sits in the center, complemented by decorative elements. A wall-mounted Smart TV is positioned across from the seating, and large windows allow natural light to brighten the space.

4.95 out of 5 average rating, 115 reviews

Lovely Beachside Villa w/ Resort Amenities

Relax & Unwind at this 2 BR 2nd Floor villa at The Spa On Port Royal Sound, a private & secluded gated community on Hilton Head's scenic North End. A short stroll through beautifully landscaped gardens & lagoons, past the hammocks and koi pond, reveals Mitchellville Beach, where the Atlantic Ocean turns into the sound. The natural beauty of this unique beach draws avid birders & professional photographers. Offering 3 pools, hot tub, sauna, gym, Pickleballs &Tennis courts & grilling stations.

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, 118 reviews

6 BR, Sleeps 26, Beach Time

Just a short walk down Folly Field to the beach & locally managed by the Owner. This brand new beach house has 6 bedrooms and 4 full bathrooms. Linens, Bath Towel sets & Pool Towels included. An Amazing bunk room/play room with 6 full size bunk beds, high end furnishings, fully equipped kitchen, dining for the entire crew, 2 huge balconies with lovely lagoon views, large outdoor living area with television and shaded pool. We have thought of everything & we are at your service! PN: 040312

An aerial view captures a large pool shaped like a star, surrounded by lounge chairs. The pool area is complemented by umbrellas and seating, with a sandy beach and the ocean visible in the background under clear blue skies.

4.9 out of 5 average rating, 241 reviews

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March 2026 and completely redesigned from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa. Wake up to sunrise over the Atlantic, grab coffee on your private balcony, and walk to the beach in under two minutes. Spend the afternoon at Hilton Head’s largest oceanfront pool before ending the day with dinner and live music just steps from your condo. Beach chairs, wagon, pickleball, tennis, free parking, & close to the building's only elevator.

A neatly arranged bedroom features a spacious bed with a light-colored knitted blanket. Natural light filters through a nearby window, illuminating the room. Decorative wall art, displaying leaf motifs, complements the neutral color palette, while a circular mirror adds depth and brightness.

4.89 out of 5 average rating, 311 reviews

Anchor at the Beach ⛱ Eat & Shop at Coligny plaza!

Oceanfront building with a side view of the ocean from the balcony. Park your car and walk to everything. This beautiful 2 bed/2 bath beach condo is perfect for your family vacation or romantic getaway. No streets to cross to get to the beach! Location, location, location. Gated entry, private, and just a 5-minute walk to all the amenities of Coligny Plaza (70 Shops & Restaurants). I also provide beach chairs, umbrella, and beach cart for your convenience during your stay! #072058

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, 380 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.

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.

4.97 out of 5 average rating, 135 reviews

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, 453 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.

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

The private balcony features a dining table surrounded by chairs, offering serene lagoon views. Lush greenery frames the area, contrasting with the smooth wooden railing. Light filters through the trees, creating a peaceful outdoor setting, ideal for enjoying meals or morning coffee.

4.92 out of 5 average rating, 103 reviews

Island Club Condo: Beach, Pool, Gym, Pickleball

4.97 out of 5 average rating, 119 reviews

Oceanside Resort - Private Beach Access - 3 Pools

4.83 out of 5 average rating, 289 reviews

Boardwalk to Beach, Pools, Hot Tub!

4.94 out of 5 average rating, 149 reviews

Spacious Villa in Hilton Head Resort! STR#024945

A sandy path leads to the beach, flanked by dunes and coastal vegetation. The blue ocean stretches into the distance under a partly cloudy sky. A wooden railing guides the way down to the shore, where gentle waves meet the sand.

4.94 out of 5 average rating, 146 reviews

Sea Gem - Winter Sunshine by the Sea

4.97 out of 5 average rating, 135 reviews

Beachfront Resort Condo w/ Pool & Tiki Bar

4.83 out of 5 average rating, 223 reviews

Ground Floor Unit, Steps away from 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.

4.98 out of 5 average rating, 233 reviews

1st flr villa few mins walk to beach pools & pball

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 104 reviews

A calm beach scene is captured at dusk, featuring gentle waves lapping at the shore. The horizon showcases a soft gradient of colors, transitioning from deep blue to warm peach and pink tones. The tranquil sea reflects the fading light of dusk.

Villa in Palmetto Dunes

Spacious dog-friendly villa, walk to the beach

A bright living area is presented with a cozy arrangement of a spacious sofa and a gray loveseat. Natural light filters through window treatments, highlighting a round coffee table and decorative accessories. A console table with a mirror and a soft lamp complete the inviting space.

4.94 out of 5 average rating, 108 reviews

Hilton Head Island Beach Cottage/House

4.97 out of 5 average rating, 110 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 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, 406 reviews

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

4.98 out of 5 average rating, 110 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

Stately Governors Quarters-Pet Friendly, Fenced In

Superhost

Home in Palmetto Dunes

Blue Sky Villa: Beach/pets/golf/tennis/pickleball

4.84 out of 5 average rating, 148 reviews

4.96 out of 5 average rating, 188 reviews

Large home, beach close, pool

4.93 out of 5 average rating, 102 reviews

A private pool and spa are surrounded by lush greenery, creating a peaceful atmosphere. The pool area features a clean, inviting water surface, with a spa adjacent to it. A charming deck overlooks the pool, providing a space for relaxation.

Home in Palmetto Dunes

Walk to beach - house w/private pool/spa, pets ok

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 111 reviews

HHI Tide 21: Family Friendly, 4 Min Walk to Beach

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.

4.98 out of 5 average rating, 368 reviews

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

A view from the balcony showcases lush greenery and a tranquil pond, with a gentle fountain visible. In the distance, the ocean glimmers under a blue sky. A palm tree stands prominently in the foreground, enhancing the coastal scenery.

4.91 out of 5 average rating, 291 reviews

Hilton Head Beach & Tennis Resort Ocean View!

A thatched-roof pavilion offers shaded seating, featuring white patio furniture arranged around circular tables. The sun rises in the background, casting a warm glow, while a sandy beach and volleyball court are visible nearby, creating a welcoming space for relaxation and social gatherings.

4.9 out of 5 average rating, 238 reviews

Across from the beach and Coligny Plaza!

Superhost

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.

4.89 out of 5 average rating, 252 reviews

Oceanside Beach Retreat

The image displays a large swimming pool surrounded by lounge chairs, with a view of the sandy beach and ocean beyond. The shoreline features umbrellas for shade, while the landscape includes greenery and distant beachgoers enjoying the sun.

4.76 out of 5 average rating, 156 reviews

Relax and Unwind at this Ocean Front Resort

A modern kitchen area is showcased with stainless steel appliances and white cabinetry, complemented by a light wooden countertop. A cozy seating area is indicated by a curved sofa, while a large television sits on a wooden stand, enhancing the welcoming ambiance.

4.88 out of 5 average rating, 240 reviews

Top Floor- Ocean Views- Coastal Living