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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 small outdoor balcony features a round table with two chairs, adorned with floral cushions. Two blue cups sit atop a light blue placemat, with a view of lush greenery and trees visible in the background.
Apartment in Sea Pines
5 out of 5 average rating, 36 reviews

Steps to Ocean & Marina in Sea Pines-bikes-pool!

Free Bikes-Pool-Tennis! 2 bedroom, 2 bath Bluff Villas condo located in the heart of South Beach within the Sea Pines Resort. Steps from the beach, marina, pool & famous Salty Dog Cafe. Both baths Newly tiled/renovated amenities: - 4 bikes to use on Sea Pines' perfectly maintained wide bike paths - Pool 3 min next door(incl)-open Mem Day wknd - 1 hour/day + free walk on time-tennis at So Beach Racquet Club - new world class Pickleball facility! (reas rates) - 4 beach chairs & wagon - Spectrum

Guest favourite
The exterior of the villa features a modern design with natural wood siding. A spacious deck is adorned with a railing and small plants, providing a welcoming entrance. Large windows allow natural light into the home, surrounded by lush greenery.
Bungalow in Sea Pines
4.98 out of 5 average rating, 124 reviews

Sea Pines Resort , 5 Minute Walk to the Beach!

Completely renovated AMAZING villa.This 1 bedroom 1 bath villa is a short 5 min.(400 yards ) walk to the stunning beach!The master bedroom has a king bed and the living room sofa is queen sleeper.The kitchen is updated with stainless steel appliances and a beautiful oyster shell chandelier hangs over a 4 seat dining table.Enjoy your time on large screened in porch with privacy shades that overlooks a small lagoon & enclosed outdoor shower.Free Amazon Prime and HBO.Private pool for guests

Guest favourite
The exterior of the cottage is depicted, showcasing a two-story design with light-colored siding, surrounded by landscaped shrubs and greenery. A pathway leads to the entrance, flanked by a wooden railing, inviting access to the home.
Cottage in Shipyard
4.92 out of 5 average rating, 125 reviews

Shipyard! - Private Beach & Golf! Pet Friendly!

This 2 bed 2.5 bath cottage features access to great community amenities including private beach access and the Shipyard beach club. Within the Shipyard gates, enjoy 27 holes of championship golf courses, biking trails, restaurants, bars, spas, and the Sonesta Resort. Dozens of restaurants offering up Hilton Head Island's famous local seafood, craft beer, and "The Bank" are a stones throw away. Shopping and site seeing are a walk or bike-ride away at Coligny Plaza and Celebration Park.

Top guest favourite
The exterior of a charming villa is presented, featuring a light-colored facade and multiple balconies. A prominent sign reading 'Crown Reef at Port Royal' adds character to the landscape, while surrounding greenery and trees enhance the natural appeal of the setting.
Apartment in Hilton Head Island
4.98 out of 5 average rating, 40 reviews

Luxury Beach & Golf Villa - 5 min walk from Beach!

Location! Location! This stylish 3BR, 3.5B villa is located in a picturesque setting just a quick walk to one of the best beaches on the island, and minutes from amazing golf and tennis/pickleball. Gorgeous! Spacious! Renovated! The open layout is bright and stylish; while the fully equipped kitchen has new stainless steel appliances, plus all the tools to prepare a delicious meal. Better yet, use the shared outdoor grill & eat on your private deck after a great day at beach or golf!

Guest favourite
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.
Apartment in Hilton Head Island
4.89 out of 5 average rating, 108 reviews

Oceanfront, 3rd floor, King Bed

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 favourite
A living area is furnished with plush, neutral-toned seating that provides comfort. A large glass door reveals views of the tranquil outdoor space. Art and a wall-mounted television enhance the atmosphere, while a dining area is visible in the background.
Apartment in Harbour Town
4.9 out of 5 average rating, 30 reviews

SeaPinesVilla - Harbor Town, Free Bikes, Pets OK

Stroll to Harbour Town to enjoy the Lighthouse, dining and marina in just a few short minutes from this lovely, updated 2 bedroom Racquet Club Villa. 2335 has a tranquil lagoon view and guests can enjoy on-site pool and tennis and the ease of a neighborhood trolley stop. Located on the first floor and with sleeping for 6, this property is a great addition to our group. This property is pet friendly upon approval, but with all hard surface flooring, immaculately clean.

Guest favourite
Home in Sea Pines
5 out of 5 average rating, 17 reviews

LARGE Private Pool & Spa ~ Designer Decorated

Escape to Island Time, a 4BR/3BA retreat in Sea Pines, just 0.5 miles to the beach & 0.7 miles to the Beach Club. This spacious home features a private heated pool & spa, golf course views, a screened-in porch, and multiple indoor & outdoor living areas. Enjoy the grill (cleaned before arrival, propane included) and a Solo Stove fire pit (guest provides firewood). Experience the perfect blend of relaxation and Lowcountry charm—book your stay today!

Guest favourite
A light-filled living area features a cream-colored sofa with decorative cushions, complemented by a round wooden coffee table. In the backdrop, a mirrored wall enhances the spacious feel, while a vibrant beach-themed artwork adds a touch of coastal charm.
Flat in Hilton Head Island
4.89 out of 5 average rating, 36 reviews

First Floor - 50 Yards to Sand- Partial Oceanview

This Hilton Head Beach & Tennis Resort FIRST FLOOR, one-bedroom retreat with an ocean view from the patio. Direct beach access from the complex, less than 50 yards from the sand! In room work station. Multiple restaurants in the complex as well as bike rentals. Including a network of pedestrian trails to explore and world-class golf all within easy reach of home. Mini golf 2 minutes away. Short drive to Coligny, Harbortown, etc

Superhost
Apartment in Hilton Head Island
4.67 out of 5 average rating, 12 reviews

MyStay at 3255 Seascape – Steps to Beach & Pool!

MyStay at 3255 Seascape offers the perfect Hilton Head escape in South Forest Beach. Steps from the sand, this bright, renovated villa features stunning lagoon views, a fully stocked kitchen, and spacious bedrooms. Enjoy two pools, a private beach cabana, and easy access to Coligny’s shops, dining, and Celebration Park. Beach gear included—just bring your flip-flops! Book now and make unforgettable island memories.

Top guest favourite
A comfortable seating area includes a cozy gray sofa with patterned throw pillows. A bamboo coffee table sits in the center, surrounded by natural light from sliding glass doors leading to a balcony. Vibrant green plants add a touch of nature to the space.
Villa in Hilton Head Island
4.96 out of 5 average rating, 209 reviews

Private Beach on Sound | 3 Pools/Spa | Free Tennis

Make the most of beachfront living at this sunny retreat. Our community is closer to the water than any other resort on the island. Pack the cooler and take a short stroll to the beach. Sea’ la Vie is a ground-floor (no stairs) unique escape destination with top-of-the-line comforts of any 5-star rental or hotel. Our villa has been renovated from top to bottom.

Guest favourite
A balcony view is presented, showcasing a wooden table and chair set. A small potted plant sits on the table, with a backdrop of sandy beach and ocean waves reflecting sunlight. Lush greenery and palm trees are visible in the surrounding area.
Apartment in Palmetto Dunes
5 out of 5 average rating, 20 reviews

Luxury Oceanfront Penthouse at Villamare

Beautifully renovated oceanfront Villamare penthouse with panoramic ocean views. This spacious retreat offers a full kitchen, comfortable living area, and two bedrooms with Smart TVs and charging stations. Guests enjoy direct beach access plus two oceanfront pools with hot tubs, a fitness center, and the only indoor pool at an oceanfront resort on Hilton Head.

Guest favourite
Villa in Palmetto Dunes
4.87 out of 5 average rating, 183 reviews

Coastal Charm - Beach, pickleball, golf, pets

Welcome to your spacious and airy single-level townhome in the beautiful Palmetto Dunes Resort! With no interior stairs, this relaxing retreat is perfect for families, couples, and even your well behaved furry friends.

Popular amenities for Hilton Head Island holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Hilton Head Island's top sights

Hilton Head Island Beach & Tennis Resort

17 locals recommend

Folly Field Beach

53 locals recommend

Hilton Head Resort

7 locals recommend

Palmetto Dunes Oceanfront Resort

4 locals recommend

Coligny Plaza Shopping Center

278 locals recommend

The Sea Pines Resort

14 locals recommend

Other great holiday rentals in Hilton Head Island

Top guest favourite
A bright living area features a high ceiling and large glass doors leading to a deck, surrounded by greenery. A cozy blue sofa, a flat screen TV, and a decorative fireplace are present, along with a dining table set for six, inviting relaxation and comfort.
Townhouse in Sea Pines
4.97 out of 5 average rating, 38 reviews

Cozy 3BR/2BA in Sea Pines - Pool, Beach, Golf, Ten

Guest favourite
A spacious living area is furnished with a comfortable couch, a wicker armchair, and a coffee table. A large smart TV is positioned on a media console. Natural light enters through sliding doors, leading to an outdoor seating area, with a view of the pool.
Villa in Hilton Head Island
4.8 out of 5 average rating, 10 reviews

Charming Condo Overlooking Pool, Minutes to Beach!

Top guest favourite
A spacious living area features a soft blue sectional sofa complemented by patterned throw pillows. A glass coffee table sits in the center, adorned with a small plant and books. Natural light streams in through sliding glass doors, enhancing the inviting atmosphere.
Apartment in Palmetto Dunes
4.91 out of 5 average rating, 113 reviews

Luxury Condo King bed Pool &Ocean views hot Tub

Apartment in Hilton Head Island
4.64 out of 5 average rating, 33 reviews

Ground-floor 2BR with pool - walk to beach

The exterior of the villa is showcased, featuring a well-maintained garden with green grass and shrubs. The building displays multiple windows and a stairway entrance. A sign detailing property information is positioned nearby, offering clear views of the surrounding landscape.
Apartment in Sea Pines
5 out of 5 average rating, 4 reviews

Sea Pines villa steps to the beach

Apartment in Hilton Head Island
4.5 out of 5 average rating, 16 reviews

2BR Oceanview | Balcony | Pool | Hot Tub

Guest favourite
A wooden deck extends towards the water, offering seating under a blue and white striped umbrella. Lush greenery and coastal grass are visible on either side, with calming views of the water in the distance framed by clear blue skies.
Home in Harbour Town
4.95 out of 5 average rating, 150 reviews

Ocean-View Treetop Escape w/ Fire Pit!

Top guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 6 reviews

Brand New Lux Condo - Ocean View! Steps to Beach!

When is the best time to visit Hilton Head Island?

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Avg. price£112£114£136£153£152£177£180£155£136£130£129£124
Avg. temp10°C12°C16°C19°C23°C27°C28°C28°C25°C20°C15°C12°C

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 £15 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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