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Vacation rentals in Hilton Head Island

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Popular amenities for Hilton Head Island vacation rentals

Self check-in
Beachfront
Free parking on premises
Gym
BBQ grill

Hilton Head Island beach vacation rentals

Guest favorite
A scenic view is presented from the balcony, showcasing a coastal landscape with sprawling greenery and a sandy beach in the distance. The sky is clear with soft clouds, enhancing the tranquil atmosphere of the surroundings.
Condo in Hilton Head Island
4.93 out of 5 average rating, 187 reviews

OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6

Guest favorite
An aerial view captures a large pool shaped like a star, surrounded by lounge chairs. The pool area is complemented by umbrellas and seating, with a sandy beach and the ocean visible in the background under clear blue skies.
Condo in Hilton Head Island
4.89 out of 5 average rating, 204 reviews

Easy Breezy at Hilton Head Beach & Tennis

Guest favorite
A spacious oceanfront pool area is surrounded by lush green landscaping, featuring lounge chairs and a shallow entry. A winding path leads toward the beach, with the ocean visible in the background, flanked by tall trees creating a serene atmosphere.
Villa in Hilton Head Island
4.93 out of 5 average rating, 107 reviews

Modern Oceanfront Villa With Views and Heated Pool

Guest favorite
A modern kitchen area is showcased with stainless steel appliances and white cabinetry, complemented by a light wooden countertop. A cozy seating area is indicated by a curved sofa, while a large television sits on a wooden stand, enhancing the welcoming ambiance.
Condo in Hilton Head Island
4.88 out of 5 average rating, 200 reviews

Top Floor- Ocean Views- Coastal Living

Guest favorite
A bright and airy living space is presented with light wood paneling and modern furnishings. A comfortable sofa is adorned with decorative pillows, while a farmhouse dining table accommodates six. The kitchen features white cabinetry and a blend of patterned tiles, enhancing the open layout.
Condo in Hilton Head Island
4.92 out of 5 average rating, 106 reviews

BEACH PATH At Hilton Head Beach and Tennis Resort

Top guest favorite
A decorative shelving unit displays an assortment of illuminated lighthouses in various colors. The vibrant lighting creates a calming ambiance, highlighting unique designs in each lighthouse. Darker corners contrast with the radiant colors, enhancing the visual appeal of the arrangement.
Condo in Hilton Head Island
4.98 out of 5 average rating, 173 reviews

"Beach Time" - a cozy HHI Condo, steps from beach

Top guest favorite
A serene view of a sunset over the ocean is framed by a railing, with silhouettes of trees in the foreground. The horizon displays vibrant orange and yellow hues against a deepening blue sky, providing a tranquil backdrop to the surrounding landscape.
Villa in Hilton Head Island
4.93 out of 5 average rating, 366 reviews

Direct Ocean Front S. Forest Beach

Top guest favorite
A three-story building is depicted with multiple balconies overlooking a paved driveway. Lush palm trees line the area, providing a tropical feel. The sky is partly cloudy, suggesting a bright atmosphere. Parking spaces are visible, adding convenience for guests.
Condo in Hilton Head Island
4.98 out of 5 average rating, 266 reviews

Coastal King Beach Flat Convenient to Everything!

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Hilton Head Island fishing vacation rentals

Top guest favorite
A bright and modern kitchen space is complemented by a dining table with four chairs. Stainless steel appliances and white cabinetry provide a clean look. A comfortable seating area with two chairs is positioned near a window, enhancing the room's natural light.
Apartment in Bluffton
4.99 out of 5 average rating, 171 reviews

May River Cottage on Lawrence street, old Town.

Guest favorite
An inviting living space features a sectional sofa, a wooden coffee table, and a dining area with several chairs. Natural light illuminates the room through multiple windows, highlighting the coastal-inspired decor and airy layout. A chandelier complements the open, relaxed atmosphere.
Home in Hilton Head Island
4.94 out of 5 average rating, 116 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Top guest favorite
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
4.97 out of 5 average rating, 305 reviews

Oceanfront Luxury! KING BED 65"TVs Pickleball BAR!

Guest favorite
A modern living area features a comfortable gray sofa paired with colorful accent chairs. A coffee table sits atop a textured area rug, while large windows provide natural light. A dining table with chairs and a small balcony view enhances the inviting space.
Condo in Hilton Head Island
4.84 out of 5 average rating, 182 reviews

Beach Time! Retro-Mod Family Beach Fun

Guest favorite
A clear view of the ocean is framed by lush palm trees and greenery, highlighting the vibrant blue water and serene coastal landscape. A bright sky enhances the tranquil atmosphere, providing a picturesque backdrop to the beach scene.
Condo in Hilton Head Island
4.96 out of 5 average rating, 296 reviews

Ocean View Luxury! KING BED 65" TV Bar Pickleball GYM

Guest favorite
A spacious bedroom features a comfortable bed with striped bedding and decorative pillows. Natural light enters through double windows. A cozy sitting area with a TV, a small table, and a plant adds functionality. A ceiling fan and wooden beams enhance the architectural detail.
Apartment in Bluffton
4.92 out of 5 average rating, 185 reviews

One Bed Carriage Hse, Winnie's Corner in Old Town.

Guest favorite
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
4.97 out of 5 average rating, 140 reviews

Beach Resort Luxury 2b Villa Golf View Pickleball

Top guest favorite
A spacious bedroom features a large bed dressed in neutral linens, flanked by light wood nightstands with lamps. Natural light floods in through multiple windows and skylights. A cozy seating area with light-colored cushions and decorative pillows provides additional comfort.
Home in Bluffton
4.98 out of 5 average rating, 163 reviews

Old Town Bluffton Cottage + FREE Golf Cart!

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Pet-friendly vacation rentals in Hilton Head Island

Superhost
An outdoor deck features a shapely pool surrounded by lounging chairs. Lush greenery and palm trees are visible in the background, offering a view of the golf course. A purple umbrella stands next to the pool, providing shade.
Home in Hilton Head Island
4.84 out of 5 average rating, 134 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Top guest favorite
Bright blue umbrellas are seen shading wooden chairs on a sandy beach. Two bicycles are parked nearby, with gentle waves and an expansive ocean in the background. A tranquil atmosphere is created by the soft beach grass and light shoreline.
Apartment in Hilton Head Island
4.91 out of 5 average rating, 166 reviews

Hilton Head Beach Getaway

Top guest favorite
A combined living and sleeping area features a gray couch with decorative pillows, a small coffee table, and a light-colored area rug. A twin bed with a white quilt and pillows is visible in the background, with large windows draped in yellow curtains allowing natural light to enter.
Guesthouse in Hilton Head Island
4.93 out of 5 average rating, 207 reviews

Alli B's Air B and B-Great Country access off 278

Guest favorite
A serene pool area is surrounded by lush greenery, with a paved walkway leading to the water. Several lounge chairs are positioned near the pool, which is framed by a low fence. Mature trees provide ample shade, enhancing the tranquil atmosphere.
Condo in Hilton Head Island
4.84 out of 5 average rating, 167 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Top guest favorite
The exterior of the bungalow is depicted, surrounded by lush greenery. A wooden deck leads to the entrance, framed by a fence. Clear signage indicates private parking available on the paved area, enhancing the accessibility of the property.
Bungalow in Hilton Head Island
4.95 out of 5 average rating, 108 reviews

Closest to Beach Path, Screened Porch, 1 dog ok

Guest favorite
A spacious dining area showcases a light wood rectangular table surrounded by four upholstered chairs. A centerpiece bowl sits atop the table, and place settings with plates and cloth napkins are neatly arranged. A modern light fixture hangs above, illuminating the open layout shared with the kitchen.
Cottage in Hilton Head Island
4.92 out of 5 average rating, 143 reviews

A "WOW" factor-Palmetto Dunes Retreat in Turnberry

Guest favorite
A two-story house features a light blue exterior with white trim and black shutters, showcasing a spacious driveway. A six-person black golf cart is parked in front, contrasting against the landscaped area with tropical plants and a nearby streetlamp.
Home in Hilton Head Island
4.93 out of 5 average rating, 212 reviews

The Perfect Family Vacation

Guest favorite
The open living area features new reclining furniture arranged around a coffee table. A flat-screen TV is positioned on a media console against the wall. Light-colored tiles and a patterned area rug enhance the spaciousness, complemented by a ceiling fan and decorative shelving.
Villa in Hilton Head Island
4.9 out of 5 average rating, 108 reviews

Walk to the Beach, One Level Villa, COMFY beds

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Quick stats about vacation rentals in Hilton Head Island

  • Total rentals

    6.4K properties

  • Nightly prices starting at

    ﺩ.ﺇ37 before taxes and fees

  • Total number of reviews

    140K reviews

  • Family-friendly rentals

    5.2K properties are a good fit for families

  • Pet-friendly rentals

    1K properties allow pets

  • Rentals with a pool

    5.7K properties have a pool

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.

The best time to stay in a vacation rental in Hilton Head Island

If you want to visit Hilton Head Island at its busiest and most lively time of year, come during the high summer months of June, July, and August. A golf tournament every spring draws throngs of visitors, but otherwise April and May tend to be quieter times to enjoy the calmer side of island life. Visiting in September or October will also mean mild weather and few crowds, though be careful to check the hurricane forecast as tropical storms can hit in late-autumn. The Island quiets down throughout the winter, and if you choose to come at this time of year, you may just find yourself with a 25,000 acre private island resort at your fingertips — though know that it won’t be the best time for swimming in the ocean.

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 970 villa rentals to over 1,480 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • 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.

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