Family-friendly vacation rentals in Hilton Head Island

4.98 out of 5 average rating, 118 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!

Indoor spacesFamilyQuiet

4.96 out of 5 average rating, 135 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

Lovely 3 BR home on #2 tee of the Fazio golf course in Palmetto Dunes Resort. Near tennis/pickleball center, general store, & restaurants. Newer pool and spa. Quartz countertops. Two King BRs, 3rd BR with 2 Queens. Flat screen TVs, cable, ROKU in all BRs. Doorbell cam at front door porch with recording capability for host/guest safety. Beach access @ Omni resort and Dunes House is 5-10 min by bike or 15 min walk. Beach towels/umbrella/chairs not provided. Pool/spa heat unavailable after 6/1/26

Indoor spacesFamilyGetting around

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, 145 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.

FamilyKitchenParking

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 out of 5 average rating, 108 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!

FamilyIndoor spacesParks

A candle is displayed on a table, surrounded by seashells, with a sunset view of the ocean in the background. The warm colors of the sky reflect off the water, while a cup is placed nearby, adding to the serene atmosphere of the balcony.

4.99 out of 5 average rating, 140 reviews

Big Ocean View KING BED 75"TV Beach Bar Pickleball

✨Top Airbnb Guest Favorite Home✨ Big Ocean Views - Living Room & Balcony Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar FREE Pickleball, Tennis, Gym & More KING BED + 75" & 65" Smart TVs Expanded Bedroom HGTV Featured Decorator 100% NEW Luxury renovation Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille 3 Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley

Indoor spacesKitchenCheckout

Apartment in Hilton Head Island

The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven. White cabinetry with glass accents showcases dishware. A marble countertop provides ample workspace, and recessed lighting brightens the room, enhancing its inviting ambiance.

4.97 out of 5 average rating, 167 reviews

Fully Renovated 2 Bedroom Villa - Walk to Beach

Make yourself at home in this comfortable 2 story, ground floor Condo. Easy walk to the beach. Open concept living, dining and fully equipped kitchen and 1/2 bath on main floor. Chose either the comfy King or Queen bedroom with walk-in shower or bathtub of your choice. Private courtyard with Grill and outside seating. All this, in a setting of azaleas, palms and 20 steps to pool with stores and restaurants just 2 blocks away. Please note there is only 1 parking space available for your stay.

Indoor spacesFamilyAccess

Home in Hilton Head Island

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, 122 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.

Indoor spacesKitchenTV

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, 238 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.

Indoor spacesKitchenWalkability

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, 304 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

FamilyIndoor spacesBathroom

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, 373 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!

Indoor spacesFamilyCheckout

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, 133 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.

FamilyIndoor spacesTV

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, 449 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.

Indoor spacesKitchenAmenities

Popular amenities for Hilton Head Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

Home in Hilton Head Island

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, 115 reviews

6 BR, Sleeps 26, Beach Time

FamilyKitchenPets

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, 316 reviews

Ocean View! Remodeled! Steps to beach/Pool/Bar

Indoor spacesKitchenNearby

Superhost

5 out of 5 average rating, 3 reviews

Family Memories Are Made Better at Deer Run

Indoor spacesFamilyHospitality

Superhost

4.81 out of 5 average rating, 185 reviews

Beach Front Villa Oak Tree Lined Views to Water

Indoor spacesFamilyPool

4.86 out of 5 average rating, 121 reviews

The private heated pool area features a calming blue water surface surrounded by a stone patio. Five lounge chairs are positioned for relaxation, and a grill is located nearby, with lush greenery providing a natural backdrop and a view of the golf course beyond.

Home in Palmetto Dunes

Palmetto Dunes House: Private Pool, PDBeach, Golf

Indoor spacesFamilyBackyard

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, 237 reviews

Top Floor- Ocean Views- Coastal Living

FamilyKitchenParks

Apartment in Palmetto Dunes

5 out of 5 average rating, 8 reviews

Incredible Hilton Head condo - private beach!

FamilyAmenitiesPool

4.94 out of 5 average rating, 157 reviews

A scenic view of the ocean is displayed from a top-floor balcony. The tranquil water reflects the clear blue sky, while marshland and vegetation frame the landscape. A boardwalk is visible, leading toward the beach, enhancing access to the natural surroundings.

Condo in Palmetto Dunes

Gorgeous OCEAN Views! Resort Amenities & Beach!

FamilyIndoor spacesAmenities

Family-friendly home rentals with air conditioning

5 out of 5 average rating, 28 reviews

Apartment in Sea Pines

Harbour Town Marina Studio | Walk to Lighthouse

KitchenIndoor spacesComfort

5 out of 5 average rating, 9 reviews

A spacious backyard features a free heated pool with a paved surrounding. A cozy fire pit made of stone is accompanied by four comfortable chairs, perfect for gatherings. Lush greenery and palm trees provide a natural setting, while the home offers large windows overlooking the area.

Home in Palmetto Dunes

Palmetto Dunes Escape with Pool | Dock | Firepit

KitchenIndoor spacesRiver

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.

4.93 out of 5 average rating, 42 reviews

Starfish Beach House with Pool and Bikes

Indoor spacesFamilyHospitality

5 out of 5 average rating, 5 reviews

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

Indoor spacesFamilyWalkability

5 out of 5 average rating, 37 reviews

Treehouse in Sea Pines

Luxury Waterfront Tree House | Harbour Town | Pool

Indoor spacesFamilyBathroom

5 out of 5 average rating, 12 reviews

Home in Shipyard

Coastal Fairways

FamilyKitchenCondition

5 out of 5 average rating, 92 reviews

Sea Pines house ~ Golf Sim / Putting Green / Games

KitchenIndoor spacesPool

Cottage in Hilton Head Island

A dining area features a sleek high-top table surrounded by four blue upholstered chairs. A striped runner adorns the table, while a decorative bowl sits at the center. A patterned wall adds visual interest, complemented by a light fixture and a nearby light blue door.

4.95 out of 5 average rating, 228 reviews

Cozy Cottage 3 Min beach walk-Coligny 6 Min walk

Indoor spacesFamilyWalkability

Family-friendly home rentals with Wifi

Superhost

4.91 out of 5 average rating, 11 reviews

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

FamilyIndoor spacesCheck-in

4.99 out of 5 average rating, 71 reviews

The exterior of a two-story villa features a light-colored facade and a welcoming entrance with steps leading to the front door. Lush greenery lines the path, with manicured shrubs and palm trees enhancing the natural setting. Large windows are present throughout the structure.

Home in Shipyard

The Caddyshack - Perfect Location!

FamilyIndoor spacesGrill

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.

4.91 out of 5 average rating, 32 reviews

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

FamilyKitchenAir conditioning

Luxe

5 out of 5 average rating, 3 reviews

8 Gull Point, Sea Pines: Marsh-Front, Private Pool

PoolViewLayout

Home in Hilton Head Island

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.

4.95 out of 5 average rating, 55 reviews

5BR: 400 steps to beach Private Pool+Hot Tub+Sauna

KitchenFamilyPool

A serene pool area is surrounded by lush greenery, featuring a spacious swimming pool with lounge chairs nearby. Colorful umbrellas provide shade, and a stone patio extends around the pool, inviting relaxation and outdoor enjoyment.

4.91 out of 5 average rating, 67 reviews

Sea Pines - S. Beach Charmer - Private Pool/Spa

FamilyIndoor spacesQuiet

5 out of 5 average rating, 23 reviews

High Cotton in Sea Pines

Indoor spacesFamilyWalkability