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Holiday houses in Hilton Head

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Top-rated holiday rentals in Hilton Head

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A bright entryway is presented, featuring turquoise walls and a matching front door. A white chair is adorned with a soft coral pillow, while a decorative wreath made of seashells hangs beside the door. A welcoming sign and a beach-themed tote bag add to the coastal decor.
Home in Hilton Head Island
4.99 out of 5 average rating, 105 reviews

Charming 3BR / 2 bath beach bungalow with hot tub!

Featured in the August 2022 issue of Cottages and Bungalows magazine, this beautifully remodeled 3/2 beach bungalow is nestled in a charming neighborhood within walking distance to Folly Field beach. Enjoy a cup of coffee on the back porch in the morning, relax in the 6 person hot tub after an afternoon round of golf on the many courses nearby or sit by the fire pit and watch the stars at night. 8 Min walk to Folly Field Beach 2 Min walk to Adventure cove mini golf 6 Min Drive to golf & Tennis

ValueLocationPets

Top Guest favourite
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.
Home in Hilton Head Island
4.87 out of 5 average rating, 402 reviews

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

✔wlk to beach 500 yrds, bike, boat, tennis, golf ✔pet-ok✔5beds✔gourmet kitchen☼sundeck✔ping pong table &games✔screened outdoor area with grill&table✔Spectrum&AppleTV*Roku&WiFi✔W&D✔Busn traveler ready✔2 garages✔private yard space✔1st-floor kitchen, living room with love seat and cal king sofa✔semi-open sitting room aka bdrm with cal king sofa, adjacent small closet, powder room✔sun porch✔2nd floor 2 bdrms with a queen✔master bdrm with king bed Tempurpedic, wlk-in cl and bath with ♥♥shower, 2Z AC

LocationValueParking

Guest favourite
A newly constructed beach house is shown from the front, featuring a light blue exterior and a welcoming porch. Palm trees frame the scene, complemented by manicured landscaping. A driveway leads to a two-car garage beneath the home, creating a spacious entryway.
Home in Hilton Head Island
4.98 out of 5 average rating, 86 reviews

Beach House, Elevator, Sleeps 12

Stroll just a few steps from Fish Haul Beach to discover our haven of relaxation.This newly built beach house boasts 3 bedrooms and 2.5 baths complete with complimentary linens and bath towel sets.Enjoy a fully equipped kitchen, ample dining space,and 2 expansive balconies to soak in the coastal ambiance.Enhance your beach stay with included amenities such as boogie boards,backpack beach chairs and wagons.We've anticipated every need and are dedicated to ensuring your stay exceeds expectations!

LocationFamilyBiking

Top Guest favourite
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.
Condo in Hilton Head Island
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

ValueLocationAir conditioning

Top Guest favourite
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.
Condo in Hilton Head Island
4.97 out of 5 average rating, 315 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!

FamilyLocationQuiet

Top Guest favourite
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.
Home in Hilton Head Island
5.0 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.

ValueFamilyNearby

Top Guest favourite
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.
Condo in Hilton Head Island
4.98 out of 5 average rating, 364 reviews

Oceanfront Luxe KING BED 65TV 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 KING BED FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Beach Bar/Sports Bar 3 Restaurants Bike Rentals on Site 4 Beach Boardwalks Gated 24/7 Security Seasonal Island Trolley Stop

FamilyLocationLaundry

Top Guest favourite
Apartment in Sea Pines
5.0 out of 5 average rating, 28 reviews

Harbour Town Marina Studio | Walk to Lighthouse

Cozy, bright penthouse studio with direct views of the Harbour Town Marina, just steps from the lighthouse, shops, dining, and golf. The space features a comfortable sleeping area with king bed, sitting space, kitchenette, and full bath with tub/shower combo. Enjoy the small private balcony, perfect for morning coffee or evening sunsets over the marina. Ideal for 1–2 guests looking to enjoy the Harbour Town lifestyle in Sea Pines. Located on the fourth floor with convenient elevator access.

ValueLocationKitchen

Guest favourite
Home in Palmetto Dunes
5.0 out of 5 average rating, 20 reviews

Palmetto Dunes Beach House

Completely Renovated, designer decorated home with private pool/built in spa. One level EASY walk to the beach (15 mins) ...or call the Dunes Buggy, free of charge, to pick you up and bring you back! Open floor plan with large bedrooms (King, Queen, 3 Doubles). Plenty of space inside and out to relax. Situated on a body of water overlooking the the 9th hole of Robert Trent Jones Golf Course. pool/spa -extra fee Bring the whole family to this great place with lots of room for fun.

FamilyLocationBackyard

Top Guest favourite
A modern kitchen features smooth white cabinetry and granite countertops, complemented by stainless steel appliances. A double basin sink is situated near the window, with a microwave and oven built into the cabinetry. Soft, recessed lighting illuminates the workspace.
Condo in Hilton Head Island
4.95 out of 5 average rating, 241 reviews

Heron's Haven on Port Royal Sound, 2BR/2BA

Do you love nature? Walking on the beach? Birding? Photography? Tennis? Golf? Shopping? Wonderful restaurants? This is our beautiful Villa that is located in Port Royal Sound directly on the most unique and natural beach on the island. On both sides are public parklands and nature preserves to walk and view the wildlife. A perfect location to enjoy all that Hilton Head has to offer, yet it is quiet, serene and away from all the crowds. It's why we love it, and we're sure you will too.

FamilyValueNearby

Top Guest favourite
A seagull walks along the shoreline, where gentle waves meet the sand. The tranquil ocean reflects soft pastel colors as daylight begins to fade, creating a serene atmosphere. The beach is vast, with a stretch of smooth sand visible in the foreground.
Apartment in Hilton Head Island
4.99 out of 5 average rating, 359 reviews

Hilton Head Seaside Vacation Rental

Stay in a unique, quiet beachfront neighborhood for your vacation on HHI. Enjoy a 5 minute/2 block WALK TO THE BEACH, 2 FREE bikes, Roku with NETFLIX, and a mid-island location for easy access to local attractions. Step inside to a bright, super clean, well stocked place with all of the comforts of home. Outside, you are surrounded by Live Oaks and natural landscaping. The apt. features LR/kitchen combo, 1 bedroom w/ a queen bed, full bath, W/D in walk-in closet, and a deck w/ seating.

LocationFamilyHospitality

Guest favourite
A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.
Condo in Hilton Head Island
4.96 out of 5 average rating, 222 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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**

LocationFamilyOutdoor spaces

Popular amenities for Hilton Head holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Hilton Head

Guest favourite
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
5.0 out of 5 average rating, 9 reviews

Palmetto Dunes Escape with Pool | Dock | Firepit

FamilyLocationRiver

Guest favourite
A scenic view of a natural shoreline is captured, showcasing a sandy beach bordered by calm water and grassy areas. Soft blue skies with scattered clouds create a peaceful atmosphere, while a distant couple can be seen walking along the shore.
Apartment in Hilton Head Island
4.9 out of 5 average rating, 79 reviews

2BR, 2 Min to Beach, Pool, Tennis, King Bed

FamilyLocationGetting around

Superhost
Home in Sea Pines
5.0 out of 5 average rating, 3 reviews

Family Memories Are Made Better at Deer Run

FamilyPoolIndoor spaces

Guest favourite
Condo in Hilton Head Island
5.0 out of 5 average rating, 5 reviews

Pet-Friendly | 5 min. Walk to Beach | First Floor

LocationFamilyBeach

Top Guest favourite
Condo in Hilton Head Island
4.93 out of 5 average rating, 44 reviews

Luxury Oceanfront Escape|Beachfront Resort

ValueLocationWi-Fi

Top Guest favourite
A scenic view of the waterway at sunset, featuring gentle reflections of a pastel sky. Lush marshland and distant trees line the banks, enhancing the natural beauty of the surrounding landscape.
Condo in Shelter Cove
4.99 out of 5 average rating, 91 reviews

Pet friendly condo with amazing Broad Creek views

FamilyLocationAir conditioning

Top Guest favourite
Apartment in Sea Pines
5.0 out of 5 average rating, 15 reviews

Sea Pines Villa: Pool, Tennis & Golf

FamilyLocationSleep quality

Top Guest favourite
Apartment in Hilton Head Island
5.0 out of 5 average rating, 7 reviews

Luxury 2026 Renovation+Oceanfront Views!

LocationFamilyWalkability

Frequently Asked Questions

  • Where is Hilton Head located?

    Hilton Head is an island town along the Atlantic coast of South Carolina, set within the Lowcountry region. It is known for sandy beaches, maritime forests, and coastal wetlands.

  • When is the best time to visit Hilton Head?

    Late spring and early fall are often recommended for pleasantly warm weather and vibrant local events. Summer is popular for beach activities, while winter and early spring have cooler temperatures and lighter crowds.

  • How old is Hilton Head?

    Communities on Hilton Head trace histories back thousands of years, with Indigenous peoples living on the island long before European exploration in the 1500s. Modern development expanded in the twentieth century, especially as it became a resort destination.

  • Why was Hilton Head built?

    Initially, Hilton Head was settled for agriculture and trade, becoming known for crops produced on plantations. Its transformation into a resort area was guided by interest in coastal recreation, natural beauty, and the desire to preserve local ecology.

  • What are some things to do near Hilton Head?

    Travelers can explore sandy beaches, wildlife preserves, and nature trails near Hilton Head. The area has golf courses, bike paths, and opportunities to experience local Gullah culture, waterfront dining, and art galleries.

  • How is the weather near Hilton Head?

    Hilton Head has mild winters, with temperatures typically from 40–61°F (4–16°C), and warm summers around 74–92°F (23–34°C). Rainfall is more common in late spring and summer, so visitors often pack layered clothing and light rain gear.

  • How was Hilton Head built?

    Hilton Head’s landscape was shaped by natural processes and later developed for agriculture, with plantation systems built and worked by enslaved labor. In the mid-twentieth century, thoughtful planning guided the transition to residential neighborhoods, resorts, and protected green spaces.

  • What is the history of Hilton Head?

    Hilton Head holds histories shaped by Indigenous communities, European colonization, and plantation-era developments worked by enslaved Africans. The island has preserved Gullah heritage and played roles in the Civil War, evolving into a popular coastal destination.

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