Holiday rentals in Hilton Head Island

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Top-rated holiday rentals in Hilton Head Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Sea Pines
4.99 out of 5 average rating, 143 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 private balcony features two weathered gray rocking chairs, offering a view of scenic landscaping and the ocean in the distance. Sunlight filters through nearby trees, creating a serene outdoor space that invites relaxation.
Flat in Hilton Head Island
5 out of 5 average rating, 26 reviews

Ocean Front Condo w/ Private Water Front Balcony

Never let the ocean views out of sight or from the comfort of your sun lit living room or your private waterfront balcony with a coffee watching an amazing sunrise or a cocktail watching the day melt away at this beautifully redecorated Sea Side Villa condo. Coligny Plaza is just up the block. This beachfront location, is steps from white-sand beaches and the on-site outdoor pool. Thoughtful interior upgrades include all new furniture, a new bedroom mattress and box spring and new smart TVs.

Guest favourite
A spacious living area is presented with large windows offering views of the surrounding greenery. Two armchairs and a sectional sofa provide comfortable seating, while a circular coffee table sits on a patterned rug. Soft lighting is provided by floor lamps, enhancing the inviting atmosphere.
Townhouse in Hilton Head Island
4.91 out of 5 average rating, 212 reviews

Stylish Tennis-Golf- Beach Retreat-Renovated!

Welcome to my home! The condo is located in a lush gated community with tennis, golf, and beach, south end of the island, close to all the tourist attractions. Things you can do without getting in your car: stroll on the beach, have a meal at the Sonesta resort, suntan at the community pool, play golf or tennis, ride bicycles. Pet's MUST be included in reservation dropdown at booking. Approval for 2nd dog prior to booking with additional fee charged. Pets are not allowed on the furniture.

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, 344 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
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, 117 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 large, colorful turtle sculpture is seen in a natural outdoor setting. The turtle features a intricately designed shell in earthy tones and vibrant blue flippers, perched on a textured rock with white, oval shapes resembling eggs located at its base.
Flat in Hilton Head Island
4.95 out of 5 average rating, 128 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, 111 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.

Superhost
An aerial view presents the resort's beachfront location, featuring a wide sandy beach leading to the ocean. The resort complex is surrounded by lush greenery and landscaped areas. On-site, lagoon-style pools are visible along with palm trees and sun loungers, depicting a tranquil vacation atmosphere.
Apartment in Hilton Head Island
5 out of 5 average rating, 3 reviews

Marriott Barony Beach 2BR/2Bath Sleeps 8

Beautiful two bedroom, two bath villa that sleeps 8 at Marriott's Barony Beach Club on Hilton Head Island. Condo is 1,300 sq. ft. with king bed in the master, two queens in BR2, sofa bed in the living room, two full bathrooms, fully equipped kitchen, dining area, washer and dryer, flat screen TV's, private balcony, Jacuzzi tub, and free Wifi Internet. Resort is on the beach and has heated indoor & outdoor pools, kid's pool, hot tubs, sauna, gym, & free parking.

Top guest favourite
Home in Sea Pines
5 out of 5 average rating, 82 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
Home in Hilton Head Island
5 out of 5 average rating, 5 reviews

Private Pool + Golf Views | Relaxing HHI Retreat

Designer-renovated 3BR coastal home in Palmetto Dunes with private heated pool and stunning golf course views. Just a 9-minute walk to the beach, this spacious retreat sleeps 8 and features a gourmet kitchen, screened porch, and outdoor dining. Enjoy resort perks including golf, tennis, biking, and lagoon activities. Beach gear included. Perfect for families, golf trips, and relaxing Hilton Head getaways near Shelter Cove, dining, and more.

Guest favourite
The treehouse is nestled among lush greenery, elevated on stilts to enhance views of the surrounding nature. A spacious deck extends from the front, featuring a swing chair suspended from the overhang. Brick pathways lead to the entrance, framed by vibrant landscaping.
Treehouse in Sea Pines
5 out of 5 average rating, 17 reviews

Roxy’s Hideaway | Harbour Town RBC Heritage Oasis

Roxy’s Hideaway — brand new Sea Pines Treehouse, steps from Harbour Town & RBC Heritage! Enjoy exclusive comfort in nature, close to shopping, dining and more. Pet-friendly and ideal for high-end travelers, including pro athletes. Experience unmatched service and bespoke amenities—now including an EV charger. Relax in our hammock throne, surrounded by nature and serene unaugmented ocean views, with pool access at the Harbour Town Pool!

Luxe
Home in Sea Pines
5 out of 5 average rating, 5 reviews

44 Heritage, Sea Pines: Retreat on 11th Tee of HT

Set alongside the 11th tee box of the famous Harbour Town Links, this exclusive villa on Hilton Head Island is the perfect home base for your next golf vacation or family getaway. When you’re not out on the golf course, take a refreshing dip in the South Beach community pool or head down to the sandy beach. In the evening, check out South Beach Marina Village. Copyright © Luxury Retreats. All rights reserved.

Popular amenities for Hilton Head Island holiday rentals

When is the best time to visit Hilton Head Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$188 SGD$192 SGD$229 SGD$258 SGD$255 SGD$298 SGD$304 SGD$260 SGD$229 SGD$220 SGD$217 SGD$210 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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