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Holiday rentals in Hilton Head

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Top-rated holiday rentals in Hilton Head

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Top guest favourite
A panoramic view from the balcony showcases the sparkling ocean and expansive blue sky. Below, palm trees dot the landscape, while the beach is glimpsed in the distance. A pool area is visible, framed by well-maintained greenery, with parking spaces filled with vehicles.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 198 reviews

Ocean View KING BED 65"TV Beach Bar Pickleball GYM

✨Airbnb Top Guest Favorite✨ Oceanfront Building Ocean & Pool View from Balcony Steps to Beach Bar & Pool FREE Gym, Pickleball Tennis Volleyball & More! 100% NEW HGTV Designer Renovation KING BED 75" & 65" SmartTVs Beach Chairs, Boogie Boards, Ice Chest & More Marble Kitchen/Spa Bath Top Floor WiFi 557 Mbps Elevator RESORT: No Resort Fees Huge Oceanfront Pool Tiki Beach Bar & Grille- Feb-Nov Sports Bar Bike Rental Gym & Tennis Gated 24/7 Security Free Island Trolley (Apr-Sept) 4 Beach Boardwalks

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!

Guest favourite
Sunset is captured through a cluster of palm trees, creating a warm glow against the backdrop of the sandy beach. The scene highlights the silhouettes of the trees as the day transitions to twilight, offering a serene and tranquil atmosphere.
Villa in Hilton Head Island
4.9 out of 5 average rating, 31 reviews

Fabulous view!

Gorgeous oceanfront Villa! Steps from the ocean! This 2-bedroom 2 full newly remodeled baths direct beach access Villa with private balcony that offers views of the beach, ocean and pool. Sit and enjoy coffee, wine, a good book or whatever else you like while enjoying the sight and sound of waves, passing boats and, if you are lucky, dolphins! Inside you will relax in the newly painted living room that has been artfully arranged to take maximum advantage of the view and the flat-screen T.V.

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, 355 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 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.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 227 reviews

Oceanfront Luxury! KING BED Beach Bar & Pickleball

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

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 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.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 359 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! 💕

Top guest favourite
A stunning sunrise illuminates the ocean, casting a warm golden glow across the water's surface. Rays of sunlight stretch outward, reflecting off the gentle waves. The shoreline is visible, framed by soft grasses, enhancing the tranquil morning scene.
Apartment in Hilton Head Island
4.99 out of 5 average rating, 197 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, 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! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! 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**

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!

Our newly renovated 2 BR/2 BA Fiddler's Cove villa is available for rent! Located on the quiet third floor, 24E is spacious and modern. The kitchen features new cabinets, quartz countertops, GE appliances, and floating shelves. Behind barn doors are the washer, dryer, and pantry. Updated bathrooms have new vanities and tile. The dining area includes a coffee/wine bar and seating for six. The living area has a queen sleeper sofa, side chairs, and a 65-inch TV.

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

Escape the crowds and discover the "quiet side" of Hilton Head. Our freshly renovated (Oct 2025) second-floor end unit offers a rare dual-view experience: watch the sunrise over the Atlantic (peek-a-boo view) and the calm lagoon right from your private screened porch. Whether you’re here for a romantic retreat or a family adventure, you’ll enjoy a bright, coastal-chic sanctuary just steps from the pristine shores of the Port Royal Sound.

Top guest favourite
An open concept living area showcases wood-paneled ceilings and large windows, allowing natural light to fill the space. A sectional couch faces a TV, while a wooden dining table is set for meals. Sliding glass doors open to views of the backyard.
Home in Hilton Head Island
4.97 out of 5 average rating, 58 reviews

Sea Pines Villa - Walk to Beach, Golf and Tennis

This pristine Sea Pines villa has undergone significant renovations and upgrades, enhancing your stay with modern comforts and amenities. Just a five-minute stroll to the beach, this property is perfect for beach vacations and golf trips. Enjoy views of the tree-lined lagoon and renowned Atlantic Dunes Golf Course. The villa offers a private, professionally maintained putting green, and private tennis courts are only steps away.

Popular amenities for Hilton Head holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Hilton Head

Guest favourite
An expansive pool deck is illuminated with soft lighting, showcasing a private pool and built-in spa. A lounge area with multiple chairs is present, and a covered seating area is visible in the background. The setting sun casts warm hues over the space.
Home in Hilton Head Island
5 out of 5 average rating, 5 reviews

Upscale Retreat w Pool & Spa | Palmetto Dunes

Guest favourite
Flat in Hilton Head Island
5 out of 5 average rating, 8 reviews

SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest

Guest favourite
The living room features a gray couch and a blue upholstered lounge chair. A wooden coffee table sits in front of them. Natural light enters through sliding glass doors, leading to a balcony. Coastal-themed artwork adorns the walls.
Apartment in Hilton Head Island
4.94 out of 5 average rating, 16 reviews

Beautifully renovated 2 bed/2 bath beach villa.

Guest favourite
Apartment in Hilton Head Island
4.96 out of 5 average rating, 56 reviews

Oceanfront Luxe KING BED 75TV Beach Bar Pickleball

Superhost
Home in Hilton Head Island
4.85 out of 5 average rating, 13 reviews

8 Hollyberry - Sea Pines Home with community pool

Guest favourite
Apartment in Hilton Head Island
4.89 out of 5 average rating, 73 reviews

Beach Elegant - Oceanfront Resort - Updates 4 You

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

Guest favourite
A cozy living area is shown with a light-colored sofa and decorative pillows. A coffee table sits on a patterned area rug, with a side chair nearby. Natural light filters in through large glass doors, leading to a shaded balcony with outdoor seating.
Apartment in Hilton Head Island
4.86 out of 5 average rating, 59 reviews

Port Royal Village 302 - Walk to Beach

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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