Vacation rentals in Hilton Head Island

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Top-rated vacation rentals in Hilton Head Island

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Top guest favorite
A dining table is set for six with blue plates and clear glasses. The kitchen is visible in the background, featuring white cabinets and major appliances. A light fixture illuminates the space, while a cozy living area is accessible through an open doorway.
Condo in Hilton Head Island
4.86 out of 5 average rating, 318 reviews

Gorgeous villa, private beach access, HH Resort

Indulge in our serene & beautiful 2 bedroom beach villa with a comfy king bed. Private terrace off the master bedroom and located on the top floor so no noise above you. Our oceanside gated Resort community awaits you with private beach access-just a short walk over our picturesque boardwalk and all resort amenities are included. Shelter Cove shops, restaurants & supermarket are nearby and we are next door to Palmetto Dunes golf course. Great for families or couples. Perfect mid island location!

Top guest favorite
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.
Condo in Hilton Head Island
4.96 out of 5 average rating, 315 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! 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 favorite
Condo in Hilton Head Island
4.96 out of 5 average rating, 310 reviews

Ocean & Marsh View KING BED 65"TV Bar Pickleball!

✨ Airbnb Guest Favorite ✨ 2-3 min walk to Beach Beachfront Building Quiet Views of Coastal Marsh, Ocean & Trees - Not Parking Lot! KING BED + Big SmartTVs HGTV Decorator Designed Coastal Decor Private Top Floor Balcony Beach Chairs + Ice Chest Provided Couples Retreat! Well designed 540 square foot condo RESORT: 4 Beach Boardwalks! Huge Oceanfront Pool Beachfront Bar & Grille Sports Bar 2nd Pool FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rentals Gated w/24 Hour Security!!

Top guest favorite
Apartment in Bluffton
4.99 out of 5 average rating, 429 reviews

Guest House on Lawrence Street

UPDATED LUXURY & FASTIDOUS CLEANLINESS in one of historic OldTown Bluffton’s coziest carriage houses. OldTown’s vibe is just plain fun. Stoll to wide variety of super restaurants, night life, art galleries, boutiques, antebellum homes & lush waterfront parks on the idyllic May River. Built in 2018 w/ quartz counters, private bedroom w/ plush king-size bed, upscale bath w/ soaking tub, bright living/dining room, full kitchen w/ gas cooktop, romantic rocking-chair porch up in moss-draped oaks.

Guest favorite
Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.
Apartment in Hilton Head Island
4.82 out of 5 average rating, 177 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate renovated baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

Top guest favorite
A view from the balcony captures the serene ocean and beach during sunset. Vibrant colors reflect across the water, while lush greenery and trees frame the picturesque scene. The elegance of natural beauty is enhanced by a lantern hanging nearby.
Condo in Hilton Head Island
4.95 out of 5 average rating, 274 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your balcony. Natural beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!a

Guest favorite
A clear view of the ocean is visible from the balcony, showcasing a sandy beach lined with colorful umbrellas. Gentle waves roll onto the shore, and distant figures can be seen enjoying the beach. Lush greenery frames the foreground, enhancing the coastal scene.
Condo in Hilton Head Island
4.89 out of 5 average rating, 99 reviews

Oceanfront, 3rd floor, unobstructed ocean views

Direct oceanfront! Perfect for a couples get away, week vacation or anything in between. Take a walk across the street to Coligny Square where there are more than 60+ shops and restaurants. Ride your bike on more than 100 miles of trails. Onsite parking, pool and free wifi. Just bring your bathing suit and a towel! We provide the rest for you to have a relaxing vacation; beach chairs, umbrella, cooler, all kitchen spices, a Coffee Bar, shampoo, conditions, body wash and tide pods!

Guest favorite
A bright living area features a comfortable sofa and additional seating, including a wicker chair. A coffee table sits on a decorative rug, while large sliding glass doors allow natural light and views of the outdoors. Simple decor adds a relaxed beach ambiance.
Condo in Hilton Head Island
4.94 out of 5 average rating, 161 reviews

Stay by the Beach ⛱ Eat & Shop at Coligny plaza!

Park your car and walk to everything! This beautiful 2 bedroom/1.5 bath 2-storey beach villa is perfect for your family vacation, couple's getaway, or remote work location! This location can't be beat. Just across the street from a public beach access path, and a 5-minute walk to all the amenities of Coligny Plaza (70 Shops & Restaurants) & the brand new Low Country Celebration Park! I also provide beach chairs, umbrella, and beach cart for your convenience during your stay

Guest favorite
The living area showcases a light blue sofa adorned with decorative pillows, complemented by a brown ottoman. A wooden table sits beside an equipped kitchenette featuring modern appliances. Large glass doors allow natural light and provide access to the outside balcony.
Condo in Hilton Head Island
4.78 out of 5 average rating, 206 reviews

BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN

Freshly decorated in coastal decor, this beachfront condo sleeps up to 4 and is located right by Coligny, Hilton Head's chicest neighborhood. Freshly furnished unit includes a spacious king bed and queen sofa sleeper, both fitted with luxurious memory foam mattresses. Just a three minute walk to sandy beaches, and you can catch a glimpse of gentle tides from your own private balcony! The villa is full of amenities including beach chairs, beach umbrella, games and much more.

Top guest favorite
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.
Condo in Hilton Head Island
4.99 out of 5 average rating, 163 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 favorite
A welcoming living area features a light-colored sofa adorned with decorative pillows. A round coffee table sits on a textured area rug. A large mirror and a potted plant enhance the space, while natural light enters through the door opposite the seating.
Guesthouse in Bluffton
4.97 out of 5 average rating, 792 reviews

Bluffton's Tropical Carriage House Getaway

Embrace the inviting atmosphere of this detached garage apartment. The guesthouse features an open-concept living/*kitchenette/sleeping area, a tropical design, a private entry, a luxury king mattress and blackout window treatments. This southern style hood offers ample sidewalks, ponds for fishing, a playground, and a park. Quaint Old Town Bluffton is a 3 minute drive or 20 minute walk to a number of shops and restaurants. Permit # STR21-00119

Top guest favorite
A serene beach scene features a boardwalk leading to the water, surrounded by soft sand and lush greenery. The sky is expansive, showcasing soft clouds merging with blue hues. The shoreline is visible in the distance, offering a peaceful atmosphere.
Condo in Hilton Head Island
4.98 out of 5 average rating, 130 reviews

Beach condo with pool and stunning nature views

Your peaceful and stylish condo is on Hilton Head’s hidden gem beach, with nature views, lush landscaping, 3 pools, a hot tub, and tennis. This newly remodeled 2-bed/2-bath unit features lagoon and sea views, a screened-in sunroom, new LG appliances, quartz counters, a stocked kitchen, in-unit laundry, 65" TV in the living room, 58"/55" TVs in bedrooms, beach gear (cart, umbrellas, toys), 400 MB Internet—and no cleaning fee!

Popular amenities for Hilton Head Island vacation rentals

When is the best time to visit Hilton Head Island?

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Your guide to Hilton Head Island

All About Hilton Head

There are 24 golf courses and 12 miles of soft-sand beaches spread over Hilton Head Island’s 25,000 acres. Add scenic walking trails, breezy, tropical weather, and an obsession with tennis and there’s a good chance you’re here to recreate and relax. This is an island of swaying palms, easy resort-style living, and the Southern flare for hospitality for which this neck of the woods is known. Hilton Head Island is also steeped in history, with a prominent Gullah-Geechee influence that infuses this little corner of the lowcountry with a cultural richness. There are also restaurants serving traditional Southern fare, oyster shucking stalls, and folk music and artisan wares steeped in West African tradition. With so much layered history everywhere you look, you may have come here to play, but you’ll likely leave having learned a lot too.


Top things to do in Hilton Head Island

Learn about Gullah culture

The Gullah-Geechee people of Hilton Head and the surrounding lowcountry are the descendants of enslaved West Africans who, due to the remoteness of their island plantations, managed to preserve their heritage and cultural identity throughout the centuries. Take a boat tour along the waterways that link these island communities, go on a trail walk led by a Gullah elder, or savor Gullah culture in one of the best ways possible — by tasting its influence on so much of Southern cuisine.

Golf

With two dozen golf courses on Hilton Head Island, you can rest assured that this is an excellent place to putt. The island is something of a pilgrimage site for golf aficionados, with the pros and fans alike coming down every year for the regular pro tours and annual tournaments. Note that some of the island’s golf clubs are private or membership only, but fear not, there are still more than 15 public courses that anybody can enjoy.

Sea Pines Forest Preserve

Sea Pines Forest Preserve is a haven of natural beauty, wildlife, and history. Wander along wetland boardwalks, hike through forest trails, and watch alligators bask in the marshes. While here, don’t miss the 4,000-year-old Sea Pines Shell Ring, an important indigenous archeological site, and leave some time to get lost in the secret forest, past a vanishing swamp.

Frequently Asked Questions

  • How is the weather in Hilton Head Island?

    Hilton Head Island experiences a subtropical climate. Summers are hot and humid with temperatures around 90°F (32°C), while winters are mild with temperatures around 60°F (15°C). Rainfall is evenly spread throughout the year.

  • What are some of the best things to do in Hilton Head Island?

    Visitors frequently enjoy exploring the Island's pristine beaches, playing golf on its world-class courses, cycling along the numerous bike trails, and observing wildlife at the Pinckney Island National Wildlife Refuge.

  • What is the best time of year to visit Hilton Head Island?

    Spring and summer, particularly April through June, are the most popular times to visit Hilton Head Island. This period coincides with pleasant weather and popular events such as the RBC Heritage PGA golf tournament in April and the Hilton Head Island Art Festival in May.

  • What are the best places to stay in Hilton Head Island?

    Popular areas to stay on Hilton Head Island include the Sea Pines Resort area with its golf courses and beaches, the Palmetto Dunes Oceanfront Resort area for its central location, and the Harbour Town area known for its iconic lighthouse.

  • What are the best places to visit in Hilton Head Island?

    Coligny Beach Park, Sea Pines Forest Preserve, and the Harbour Town Lighthouse are popular places to visit in Hilton Head Island. The Coastal Discovery Museum is also frequently suggested for those interested in local history and ecology.

  • What are some hiking trails in Hilton Head Island?

    Hilton Head Island has several hiking trails such as those found in Sea Pines Forest Preserve, Fish Haul Creek Park, and Jarvis Creek Park. These trails offer opportunities to explore the island's diverse flora and fauna.

  • What are some family activities to do in Hilton Head Island?

    Families can explore interactive exhibits at the Sandbox, an interactive children's museum, enjoy a dolphin-watching tour, visit the Coastal Discovery Museum, or bike along the many pedestrian-friendly trails on the island.

  • What are some of the best day trip ideas in Hilton Head Island?

    Popular day trips from Hilton Head Island include exploring the historic city of Savannah, Georgia, immersing in the natural beauty of Beaufort, South Carolina, and discovering the rich cultural heritage of the Gullah Geechee Corridor.

  • What types of vacation rentals are available in Hilton Head Island?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Hilton Head Island. From over 2,860 condo rentals, over 1,480 house rentals, over 970 villa rentals to over 520 apartment rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Hilton Head Island?

    Yes! Work meets play with ease at over 3,250 vacation rentals in Hilton Head Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about vacation rentals in Hilton Head Island

  • Total vacation rentals

    Explore 6,390 vacation rentals in Hilton Head Island

  • Verified guest reviews

    Over 149,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    5,170 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 1,060 rentals that welcome pets

  • Vacation rentals with a pool

    5,700 properties feature pools

  • Rentals with dedicated workspaces

    3,240 properties have a dedicated workspace

  • Wi-Fi availability

    6,210 of Hilton Head Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront, and Free parking on premises across Hilton Head Island rentals

  • 4.7 Average rating

    Hilton Head Island stays receive an average rating of 4.7 out of 5 from guests

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