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Holiday rentals in Hilton Head

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Top-rated holiday rentals in Hilton Head

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Guest favourite
Apartment in Hilton Head Island
4.96 out of 5 average rating, 57 reviews

Oceanfront Luxe KING BED 75TV Beach Bar Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨ Ocean Sunrise / Hear the Waves ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball HGTV Decorator Renovation KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM WiFi 515 Mbps Coastal Décor TOP FLOOR w/Elevator Couples Escape! Beach Chairs, Boogie Boards, Ice Chest & More! RESORT No Resort Fees Beachfront Pool w/Tiki Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)

Top guest favourite
A wooden boardwalk leads to a sandy beach, where beach umbrellas dot the shoreline. Soft waves lap at the shore beneath a clear blue sky with fluffy clouds, creating a serene coastal scene.
Townhouse in Hilton Head Island
4.98 out of 5 average rating, 164 reviews

Beachfront Resort 2b Golf Lagoon Pickleball Tennis

✨Top Airbnb Guest Favorite Home✨ Gated Beachfront Golf Resort! Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis - across street HGTV Decorator designed Panoramic Golf & Lagoon Views XL Double Porch Lush Scenery - Tons of Wildlife! Coastal Décor Sunny 1st Floor End Unit KING BED + 2 QUEENS 3 XL SmartTVs FAST WIFI & CABLE Chef's Kitchen Washer/Dryer BBQ Beach Cart, Chairs, Boogie Boards, Ice Chest Walk/Bike to Beach Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

Top guest favourite
Home in Hilton Head Island
5 out of 5 average rating, 88 reviews

Sea Pines house ~ Golf Sim / Putting Green / Games

Town of Hilton Head Island STR Permit Number: 064406 Centrally located in Hilton Head Island just within the gates of Sea Pines, with golf simulator, outdoor putting green, 2 game rooms, and a backyard area with games, outdoor dining, fire table & seating, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 kings and 4 doubles), this luxurious space will offer unparalleled comfort, amenities, and the perfect location for you to use as your central base to enjoy the best of HHI.

Top 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
4.99 out of 5 average rating, 81 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!

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.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 305 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!

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 out of 5 average rating, 118 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.

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.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 356 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 FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

Top guest favourite
A modern kitchen features a spacious marble countertop with seating for four. Well-appointed cabinetry and updated appliances are visible, enhancing the kitchen's functionality. Soft lighting illuminates the area, creating a welcoming environment for cooking and dining.
Villa in Hilton Head Island
5 out of 5 average rating, 37 reviews

Prime Waterview! Hilton Head Shelter Cove Marina

Permit 073816 Enjoy easy access to everything Hilton Head has to offer from this centrally located Condo in the heart of Shelter Cove Marina. Not only will you have breathtaking views of the sunset and the marina right from your balcony, but you also have many amenities right at your doorstep! Shelter Cove is one of the main attractions on Hilton Head Island with many shops, restaurants, weekly entertainment and water sports. You also have access to the private Palmetto Dunes Beach community.

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.
Flat in Hilton Head Island
4.99 out of 5 average rating, 353 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.

Top 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.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 217 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**

Top guest favourite
An ocean view is captured from the fifth floor, showcasing a sandy beach with gentle waves lapping at the shore. Lush greenery and a playground area are visible in the foreground, framed by nearby buildings and an inviting blue sky.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 75 reviews

Island Club 4502-Beautiful Ocean View

Our two bedroom ocean view villa will comfortably sleep 5-7. Our unit has an oversized balcony. The master suite includes a king size bed and master bath. The guest room includes two full size beds with its own bath. The Island Club maintains gas grills from a picnic area. The Island Club has nine free tennis courts, a large heated pool with a children's pool, a tanning pool, fitness center, hot tub, basketball, and bike rentals. Check out our condo's reviews at VRBO 513502.

Superhost
Treehouse in Hilton Head Island
5 out of 5 average rating, 4 reviews

Waterfront Tree House | HT Pool | Private Office

One of our newest homes, see our over 1000 *5*-star reviews. Calibogue Escape-Harbour Town Treehouse in Sea Pines Sailboats, Dolphins, Sunsets, what else could you ask for? This treehouse offers floor-to-ceiling windows with unparalleled views and the perfect setting for a perfect escape. Located on a dead-end street on Deer Island, just steps from Hilton Head’s Harbour Town and the Yacht Basin, this hideaway could not be more perfect.

Popular amenities for Hilton Head holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Hilton Head

Top guest favourite
Flat in Hilton Head Island
4.96 out of 5 average rating, 26 reviews

Stunning Ocean View | King Bed | Beach/Pool Resort

Guest favourite
A cozy balcony area features two rattan chairs with soft blue cushions positioned around a small round table. A decorative star emblem is mounted on the wall, complemented by a potted plant. Natural light filters through the screened enclosure, enhancing the tranquil atmosphere.
Apartment in Hilton Head Island
4.78 out of 5 average rating, 23 reviews

PR Sound Beach+ POOL Views | Coastal Cottage Charm

Top guest favourite
Apartment in Hilton Head Island
4.96 out of 5 average rating, 78 reviews

Sea la Vie @Fiddler's Cove - Fitness Room

Top guest favourite
Apartment in Hilton Head Island
4.95 out of 5 average rating, 22 reviews

Steps to Beach, Water Views, 3 Pools & Hot Tub

Guest favourite
The living room features a spacious sectional sofa with decorative throw pillows, complemented by a blue accent chair. Floor-to-ceiling windows provide ample natural light and views of the surrounding landscape. Neutral-toned decor and artwork depicting fish enhance the coastal ambiance.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 81 reviews

Ocean Views at Villamare, Steps to the Beach!

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.
Apartment in Hilton Head Island
4.99 out of 5 average rating, 82 reviews

Pet friendly condo with amazing Broad Creek views

Top guest favourite
Flat in Hilton Head Island
4.97 out of 5 average rating, 30 reviews

Amanzi | Stylish Seaside Gem | Beach, Pool, Gym

Guest favourite
An expansive balcony features a cushioned sofa and side chairs, centered around a wooden coffee table. A glass-topped dining table is positioned nearby, suitable for outdoor meals. Light-colored flooring provides a pleasant contrast to the wooden railings and surrounding greenery.
Villa in Hilton Head Island
4.92 out of 5 average rating, 51 reviews

Walk to the Beach! Coastal Villa w Large Balcony!

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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