Holiday rentals in Hilton Head Island

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Top-rated holiday rentals in Hilton Head Island

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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 Shipyard
4.98 out of 5 average rating, 160 reviews

Beach Resort 2B Luxury Golf Lagoon View Pickleball

Gated Beach & Golf Resort! ✨Top 5% Airbnb Guest Favorite✨ Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis – across the street HGTV Decorator designed Panoramic Golf & Lagoon Views! Big Porch Lush Landscape 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/Drive to Beach Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

Top guest favourite
An aerial view captures a cluster of modern buildings with red roofs, surrounded by lush greenery. Sailboats are docked in the marina, with a scenic waterfront area in the background. A glimpse of residential areas and palm trees adds to the inviting atmosphere.
Guest suite in Shelter Cove
4.93 out of 5 average rating, 367 reviews

Prime Spot: Harbour, Dining, Shops & Beach

Stay in the heart of it all at this upscale, centrally located guest suite (256 sq ft) with independent entrance, total privacy, queen bed and full bath (no kitchen). Step outside to waterfront restaurants, live music, bars, shops, and summer weekly fireworks. Supermarkets and more dining are just a 10-minute walk away. Enjoy a free shuttle to attractions within 2-mile radius (April–September). Golfing, biking, fishing, and water sports all nearby, free access to Palmetto Dunes Beach community.

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, 342 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 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, 340 reviews

Oceanfront Luxury! KING BED 65"TV Pickleball & BAR

✨Top 1% Airbnb Home✨ PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony - Watch Sunrise / Hear Waves! Beachfront Pool, Bar & Grille FREE Pickleball, Tennis, Gym, Volleyball & More HGTV Designer Renovation KING BED + Two 65" SmartTVs Spa Bath Expanded Bedroom w/Blackout Sleeping Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

Top guest favourite
Home in Sea Pines
4.99 out of 5 average rating, 139 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 light-filled living area features a white sofa complemented by a blue accent chair. A decorative table with a tray of flowers and a plush area rug enhances the space. Large glass doors open to a balcony, offering expansive views of the ocean.
Apartment in Hilton Head Island
4.98 out of 5 average rating, 161 reviews

My Blue Heaven, Direct Ocean Front View

Welcome to our ocean front rental, a haven for couples seeking a romantic and stylish getaway. With its breathtaking ocean view, five-star reviews, and recent remodel in 2023, this rental promises an unforgettable experience. Our guests have praised the attention to detail, the stunning view, and the overall ambiance of the space. Rest assured that your stay will be nothing short of extraordinary. Step out onto the balcony and take in the fresh sea breeze as you relax in the swinging chair.

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, 210 reviews

Oceanfront Luxury! KING BED Pickleball + Beach Bar

✨Airbnb top 10% Home ✨ PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Oceanfront Balcony See & Hear the Waves! Sunrise over Ocean 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 Beachfront Pool w/Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Trolley Stop - April-Sept

Guest favourite
Apartment in Hilton Head Island
4.87 out of 5 average rating, 255 reviews

Shore To Please! Oceanview couples retreat w/bikes

Stylish beach retreat with ocean views and modern Scandinavian design! This newly renovated villa is just steps from the beach and within walking distance of great shops, restaurants, and entertainment. Enjoy a beautifully stocked kitchen, new flooring, a walk-in shower, and a separate bedroom with a desk—perfect for remote work. Dine with an ocean view on the balcony or at the kitchen island. Beach chairs and two bikes included for exploring. First-floor location with easy beach access!

Guest favourite
The outdoor space features a year-round heated pool surrounded by lush greenery, with a clear view of the ocean. Umbrellas offer shade over picnic tables, while tall trees enhance the serene atmosphere of the beachside setting.
Villa in Hilton Head Island
4.96 out of 5 average rating, 114 reviews

Oceanfront Scandi Oasis Amazing View & Heated Pool

Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

Superhost
A view from the patio showcases palm trees swaying gently in the breeze, with sandy beach and ocean visible in the distance. Outdoor high-top table and chairs are positioned for guests to enjoy the surroundings.
Apartment in Hilton Head Island
4.81 out of 5 average rating, 121 reviews

Ocean View! 2 Min to Beach~Updated~2 Bikes #132

AWESOME OCEAN VIEWS! 1 bedroom, 1 bath condo in a gated resort with Pool! Air vent in bedroom, updated fully equipped kitchen, new paint, new ceiling fans, newer bedding with new mattress and newer couch, beach chairs, so many upgrades and it comes with 2 bikes! Close to Coligny shopping and restaurants and minutes to the beach! You just can't go wrong with this condo. Super clean and maintained! 2 TV's, DVD, Radio and awesome views! New patio furniture! The pool is not heated.

Guest favourite
A neatly arranged bedroom features a spacious bed with a light-colored knitted blanket. Natural light filters through a nearby window, illuminating the room. Decorative wall art, displaying leaf motifs, complements the neutral color palette, while a circular mirror adds depth and brightness.
Apartment in Hilton Head Island
4.89 out of 5 average rating, 277 reviews

Anchor at the Beach ⛱ Eat & Shop at Coligny plaza!

Oceanfront building with a side view of the ocean from the balcony. Park your car and walk to everything. This beautiful 2 bed/2 bath beach condo is perfect for your family vacation or romantic getaway. No streets to cross to get to the beach! Location, location, location. Gated entry, private, and just a 5-minute walk to all the amenities of Coligny Plaza (70 Shops & Restaurants). I also provide beach chairs, umbrella, and beach cart for your convenience during your stay!

Top guest favourite
Apartment in Sea Pines
5 out of 5 average rating, 108 reviews

5 Star Location-Pool, Walk to Dining/Shops/Marina

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Popular amenities for Hilton Head Island holiday rentals

When is the best time to visit Hilton Head Island?

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Frequently Asked Questions

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

    Hilton Head Island has a range of neighborhoods where visitors often stay, including Sea Pines, Palmetto Dunes, and Forest Beach. These areas are known for access to beaches, dining, and activities for all types of travelers.

  • What are the best things to do in Hilton Head Island with kids?

    Families frequently explore interactive museums, join dolphin-watching cruises, or play at local beaches and parks. Mini-golf courses and bicycling along shaded pathways add to the fun.

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

    Explore the sandy beaches, kayak through scenic waterways, and visit Harbour Town for its lighthouse and harborside shops. Golf courses, cycling trails, and nature preserves are often recommended.

  • How is the weather in Hilton Head Island?

    Hilton Head Island has mild winters with temperatures around 40–61°F (4–16°C), and warmer, humid summers reaching 90–92°F (32–34°C). Rainfall occurs year-round, with the heaviest showers often in summer months.

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

    Harbour Town is known for its lighthouse and waterfront shops, while Coligny Beach Park is a popular spot for families. Pinckney Island National Wildlife Refuge draws visitors interested in birdwatching and nature walks.

  • What are some hiking trails in Hilton Head Island?

    Enjoy walking or biking trails in Sea Pines Forest Preserve, or explore the scenic paths at Pinckney Island National Wildlife Refuge. These areas feature marsh views and opportunities to spot local wildlife.

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

    Families often enjoy beach days, kayaking, biking, and visiting interactive museums. Mini-golf, playgrounds, and boat excursions are also frequently suggested.

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

    Many visitors explore nearby historic towns or take guided nature excursions in surrounding areas. Local waterways and coastal preserves around the island are also popular for day trips.

  • Are there any pet friendly accommodations available in Hilton Head Island?

    Hilton Head Island has pet-friendly stays in areas such as Forest Beach, South Beach, and Folly Field. Many rentals welcome dogs and are near dog-friendly parks or beaches.

  • What are some local tips for visiting Hilton Head Island?

    Consider renting bikes, as cycling paths connect many attractions and neighborhoods. Local traditions include sunrise beach walks and sampling seafood at waterfront restaurants; bringing insect repellent is also suggested for marsh areas.

  • What is Hilton Head Island known for?

    Hilton Head Island is known for its sandy beaches, golf courses, and scenic marshland. The area also has a distinct blend of natural beauty, outdoor activities, and coastal food traditions.

  • What are the best hidden gems to explore in Hilton Head Island?

    Visitors often uncover quieter spots like Mitchelville Freedom Park, which shares local history, or the Audubon Newhall Preserve with its tranquil nature trails. Locally owned art galleries around the island reveal regional talent.

  • What are the best foods to try in Hilton Head Island?

    Fresh seafood dishes such as shrimp and crab are frequently suggested, along with traditional Lowcountry specialties like she-crab soup and shrimp and grits. Local barbecue and pecan pie also feature on many menus.

  • What should I bring for a trip to Hilton Head Island?

    Pack beachwear, sunscreen, and a hat for sun protection, along with comfortable shoes for biking or walking. Bringing a light rain jacket and insect repellent is useful, especially if you plan to explore marshes or parks.

  • What is the nightlife in Hilton Head Island like?

    Nightlife on Hilton Head Island has laid-back bars, live music venues, and outdoor patios, especially in areas such as Coligny Plaza and Shelter Cove. Many spaces blend local food and entertainment for a relaxed evening experience.

  • What are the most popular events or festivals in Hilton Head Island?

    Hilton Head Island frequently hosts the Heritage Golf Tournament, outdoor music and food festivals in spring and summer, and art shows throughout the year. Local markets and sporting events are also popular gathering points.

  • Are there family friendly vacation rentals in Hilton Head Island?

    Many vacation rentals on Hilton Head Island welcome families, especially in Palmetto Dunes, Sea Pines, and Forest Beach. These areas have access to beaches, parks, and entertainment suited for guests of all ages.

  • When is the best time to visit Hilton Head Island?

    Late spring and early fall are frequently suggested for pleasant temperatures, fewer crowds, and outdoor activities. Many visitors also enjoy summer for its lively beach atmosphere and seasonal events.

Quick stats about holiday rentals in Hilton Head Island

  • Total holiday rentals

    Explore 6,570 holiday rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island holiday rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 147,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,420 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 1,060 rentals that welcome pets

  • Holiday rentals with a pool

    5,760 properties feature pools

  • Rentals with dedicated workspaces

    3,610 properties have a dedicated workspace

  • Wifi availability

    6,520 of Hilton Head Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Monthly stays 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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