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
Home in Sea Pines
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 newly constructed beach house is shown from the front, featuring a light blue exterior and a welcoming porch. Palm trees frame the scene, complemented by manicured landscaping. A driveway leads to a two-car garage beneath the home, creating a spacious entryway.
Home in Hilton Head Island
4.99 out of 5 average rating, 75 reviews

Beach House, Elevator, Sleeps 12

Stroll just a few steps from Fish Haul Beach to discover our haven of relaxation.This newly built beach house boasts 3 bedrooms and 2.5 baths complete with complimentary linens and bath towel sets.Enjoy a fully equipped kitchen, ample dining space,and 2 expansive balconies to soak in the coastal ambiance.Enhance your beach stay with included amenities such as boogie boards,backpack beach chairs and wagons.We've anticipated every need and are dedicated to ensuring your stay exceeds expectations!

Top guest favourite
The open-concept living space features handmade Saltillo tiles and a vaulted ceiling. A comfortable couch and a fireplace are visible along with a large dining table. A staircase leads to the upper level, enhancing the spacious layout. Sliding glass doors provide access to the outdoor area.
Home in Sea Pines
4.98 out of 5 average rating, 100 reviews

Governor’s Quarters Pet Friendly, Fenced in Yard

Welcome to Governor's Quarters- your Luxury Hilton Head Getaway Stay Lowcountry in this stately-designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from the SeaPines Beach Club and HarbourTown Golf Links and the heated community pool! Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, HarbourTown Lighthouse, & most importantly- the beach!

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.

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
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
4.97 out of 5 average rating, 118 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.

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
Apartment in Hilton Head Island
4.95 out of 5 average rating, 131 reviews

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!

Top guest favourite
Apartment in Sea Pines
5 out of 5 average rating, 113 reviews

5 Star Location-Harbourtown-Walkable Area

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.

Top guest favourite
Home in Sea Pines
5 out of 5 average rating, 85 reviews

Sea Pines house ~ Golf Sim / Putting Green / Games

Centrally located in HHI just within the gates of Sea Pines, with golf simulator, outdoor putting green, 2 game rooms, and a backyard area with games, outdoor dining, fire table & lounging areas, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 king beds and 4 double beds), this luxurious space will offer unparalleled comfort, amenities, and the perfect location for you to use as your central base to enjoy the best of Hilton Head Island.

Guest favourite
A private pool area is surrounded by lush greenery and tall trees, providing privacy and a natural setting. The pool features a built-in spa and is bordered by a spacious stone patio. Four lounge chairs are positioned nearby for relaxation.
Home in Hilton Head Island
4.93 out of 5 average rating, 30 reviews

Private Pool/Spa | Golf | Exq. Coffee | Seascape

Gourmet Coffee Lovers Paradise. And, over 1000 *5* star reviews! You found the perfect vacation home where you can enjoy a private pool with a spacious layout. Comfortably sleep 8 in 4 private bedrooms. The kitchen is fully equipped with everything needed to prepare a gourmet meal. You can enjoy dining in the large formal dining room, the sunroom adjacent to the kitchen, or outside. *The pool and spa can be heated for an additional fee.

Top guest favourite
An open concept living area showcases wood-paneled ceilings and large windows, allowing natural light to fill the space. A sectional couch faces a TV, while a wooden dining table is set for meals. Sliding glass doors open to views of the backyard.
Home in Sea Pines
4.96 out of 5 average rating, 55 reviews

Sea Pines Villa - Walk to Beach, Golf and Tennis

This pristine Sea Pines villa has undergone significant renovations and upgrades, enhancing your stay with modern comforts and amenities. Just a five-minute stroll to the beach, this property is perfect for beach vacations and golf trips. Enjoy views of the tree-lined lagoon and renowned Atlantic Dunes Golf Course. The villa offers a private, professionally maintained putting green, and private tennis courts are only steps away.

Popular amenities for Hilton Head Island holiday rentals

When is the best time to visit Hilton Head Island?

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Avg. price$209 SGD$212 SGD$253 SGD$257 SGD$255 SGD$298 SGD$303 SGD$260 SGD$228 SGD$219 SGD$217 SGD$209 SGD
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 6,100 holiday rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 139,540 verified reviews to help you choose

  • Family-friendly holiday rentals

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

  • Pet-friendly holiday rentals

    Find 1,060 rentals that welcome pets

  • Holiday rentals with a pool

    5,250 properties feature pools

  • Rentals with dedicated workspaces

    2,990 properties have a dedicated workspace

  • Wifi availability

    6,090 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

  • 4.8 Average rating

    Hilton Head Island stays are highly rated by guests – averaging 4.8 out of 5!

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