Holiday rentals in Hilton Head

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Top-rated holiday rentals in Hilton Head

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Top guest favourite
Home in Hilton Head Island
4.99 out of 5 average rating, 145 reviews

“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops

Privately-owned 2000 SF one-level home sits on a wooded corner lot conveniently located inside the entrance of Sea Pines Resort. This 3 BR, 2BA home was extensively renovated in August 2020, with inviting French-inspired coastal decor for a relaxing cozy feel. "Sea La Vie" chalet is within walking distance to grocery stores, shops, and restaurants. A short drive or bike ride takes you to the private Beach Club, housing oceanfront dining and bar, upscale facilities, and wide beaches. Bienvenue!

Top guest favourite
A tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 302 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
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, 219 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 private balcony features comfortable seating with decorative cushions and a small round table. The view showcases a serene landscape of marshland and trees under a colorful sky at sunrise, providing an opportunity for tranquil outdoor relaxation.
Apartment in Hilton Head Island
4.85 out of 5 average rating, 118 reviews

Stunning Ocean & Coastal Views | Resort Perks!

Top-floor 2BR/2BA villa with ocean, marsh & golf views. Enjoy stunning sunrises & sunsets from your balcony. 5-min walk to semi-private beach or take the seasonal shuttle. 1 mile to Shelter Cove's dining, shopping & entertainment. Resort-style community with 3 pools, gym, bike rentals & beach access—perfect for families, couples & girls’ trips! ⭐ Guests Love It! ⭐ ★★★★★ "Kim was SUPER responsive! The view was amazing. The beach was beautiful & uncrowded. My boys & I loved the boardwalk!"

Top guest favourite
Flat in Hilton Head Island
4.95 out of 5 average rating, 21 reviews

Stunning Ocean View | King Bed | Beach/Pool Resort

Wake up to ocean views from your private balcony at Hilton Head's #1-rated island resort — with beach access, the largest beachfront pool on HHI, and a king bed waiting for you. This 1BR condo offers a king bed, private balcony, fully equipped kitchen, Wi-Fi, and a sleeper sofa. Watch the sunrise, explore local restaurants, and relax in comfort. Perfect for couples and families or even solo travelers seeking a stylish and peaceful seaside escape. Your perfect beach getaway starts here.

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, 345 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.

Guest favourite
A modern kitchen is presented with white cabinetry and a granite countertop. Stainless steel appliances, including a microwave and stove, complement the design. A small wooden island is positioned in the center, contributing to a spacious and functional layout.
Apartment in Hilton Head Island
4.93 out of 5 average rating, 110 reviews

Your Beach Escape, just one block away!

Best 2 bedroom villa in Fiddler’s Cove! This is a brand new completely renovated 2nd floor villa in Fiddler’s Cove Beach and Racquet Club on the lovely island of Hilton Head. Fiddler’s Cove is a private gated 23-acre resort that has two swimming pools (one Olympic-size), Hot Tub, 10 Clay Tennis Courts, Racquetball, Children's Play areas, barbecues, and much more. Have all the extras to get you to the beach (new beach chairs, umbrella, and beach cart with coolers). Very clean and fresh!

Top guest favourite
A modern townhome exterior features a blend of white wooden siding and dark shingles, creating a striking contrast. Large windows allow natural light to fill the interior, while manicured flower beds enhance the entrance. Two garage doors offer convenient access to each unit.
Townhouse in Hilton Head Island
4.93 out of 5 average rating, 130 reviews

Luxury 3-Bdrm HHI Art Loft Townhome

Located in the private Spanish Wells area of Hilton Head Island, one of the most sought after vacation destinations in the world. Eight minute drive to Hilton Head Island beaches, golf/tennis, restaurants, bars, bike trails, and countless shopping, entertainment, and outdoor exploration activities. Kick back and relax in this calm, stylish townhome with distinct spaces for everyone. Home Owners have appointed the home with original and collected art. Convenient to Savannah & Bluffton.

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, 349 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 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, 350 reviews

Oceanfront Luxury! KING BED Beach Bar + Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves! Beachfront Pool, Tiki Bar & Grille FREE Pickleball, Tennis, Gym & More! 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 2 Bars (1 is Sports Bar!) Gated 24/7 Security Seasonal Island Trolley Stop

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, 188 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**

Top guest favourite
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.
Apartment in Hilton Head Island
4.99 out of 5 average rating, 431 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 holiday rentals

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.

Destinations to explore