Holiday rentals in Hilton Head Island
Find and book unique accommodation on Airbnb
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 $52 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!
Top-rated holiday rentals in Hilton Head Island
Guests agree: these stays are highly rated for location, cleanliness and more.
Sea Pines house ~ Golf Sim / Putting Green / Games
Town of Hilton Head Island STR Permit Number: 064406 Centrally located in Hilton Head Island 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 & seating, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 kings and 4 doubles), 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 HHI.
*Deer Island Treehouse Walkable to Harbor Town*
Floor to ceiling windows adorn this treehouse with friendly deer on a Forest Preserve in Sea Pines. 200 yards walk or bike ride to the famous Harbour Town Lighthouse & Marina with a variety of water sports, dinner cruises, shoppes and restaurants. Take a free seasonal Trolley Ride from the Harbour Town Stop to Sea Pines Beach Club or seasonal Salty Dog Marina & Pool. The Harbour Town Golf Links and Sea Pines Resort Tennis Club are a short walk. Easy beach access to 11 miles of sandy shoreline!
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!
Luxury Oceanview King Villa + Steps to Sand
Ultimate Romantic Luxury for Couples. Recently renovated and perched on the top floor, our King Villa is the architectural “Sweet Spot” of the building. Situated at the unique Y-jut, it offers a Wider, more Expansive Oceanview panorama than any other Oceanview Villa! Being at the 'point' allows you to see further down the coast with total privacy and no neighbors above you. This is the ultimate coastal escape, combining high-end boutique finishes with the quiet serenity of the highest floor.
Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar & Grille FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop
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!
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**
Shipyard Golf: Where Family Memories Shine!
Escape to paradise at 83 Kingston Dunes Road in Hilton Head's prestigious Shipyard Plantation! This charming 3BR/3BA family home sits directly on hole #6 of the scenic Galleon Golf Course, offering stunning fairway views from spacious decks. Perfect for memorable vacations, enjoy golfing, biking trails, lagoons, and just 0.7 miles to pristine beaches and Coligny Plaza. Relax, unwind, and create family memories in this peaceful, pet-friendly retreat!
4BR Coastal Elegance Chef’s Kitchen Steps to Beach
Willoughby House is a newly built luxury coastal retreat just a 3-minute walk from the beach. This spacious 4-bedroom, 3.5-bath home features designer coastal interiors, a gourmet chef’s kitchen, elegant dining for 10+, and a refined family room with fireplace and TV. Enjoy a main-level primary suite, multiple indoor and outdoor living spaces, resort-style amenities, and seamless beach access—perfect for upscale family and group getaways.
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. STR Permit Number: 076320
Waterfront Tree House | HT Pool | Private Office
One of our newest homes, see our over 1000 *5*-star reviews. Calibogue Escape-Harbour Town Treehouse in Sea Pines Sailboats, Dolphins, Sunsets, what else could you ask for? This treehouse offers floor-to-ceiling windows with unparalleled views and the perfect setting for a perfect escape. Located on a dead-end street on Deer Island, just steps from Hilton Head’s Harbour Town and the Yacht Basin, this hideaway could not be more perfect.
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
Stay near Hilton Head Island's top sights
Other great holiday rentals in Hilton Head Island
Starfish Beach House with Pool and Bikes
Oceanfront Luxe KING BED 75TV Beach Bar Pickleball
Oceanfront Hilton Head Villa | Salt & Sunrise
Updated Peaceful Direct Oceanfront 1BR Villa
Private Pool | Golf | Exq. Coffee | Seascape
Renovated 1BR HHI – Walk to Beach & Salty Dog Café
#103 Renovated/1BR/1.5BA/Ocean/Pool Views/Sofa Bed
The Lookout - A Modern Beach Retreat (Oceanfront)
When is the best time to visit Hilton Head Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $214 SGD | $216 SGD | $259 SGD | $263 SGD | $260 SGD | $304 SGD | $309 SGD | $265 SGD | $233 SGD | $224 SGD | $221 SGD | $214 SGD |
| Avg. temp | 10°C | 12°C | 16°C | 19°C | 23°C | 27°C | 28°C | 28°C | 25°C | 20°C | 15°C | 12°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.
Destinations to explore
- Four Corners Holiday rentals
- Atlanta Holiday rentals
- Orlando Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Gatlinburg Holiday rentals
- Savannah Holiday rentals
- Charleston Holiday rentals
- Jacksonville Holiday rentals
- Pigeon Forge Holiday rentals
- Kissimmee Holiday rentals
- North Myrtle Beach Holiday rentals
- Rentals with beach access Hilton Head Island
- Rentals with a firepit Hilton Head Island
- Apartment rentals Hilton Head Island
- Mansion rentals Hilton Head Island
- Rentals with a patio Hilton Head Island
- Hotel rooms Hilton Head Island
- Beach house rentals Hilton Head Island
- Villa rentals Hilton Head Island
- Rentals with a kayak Hilton Head Island
- Serviced apartment rentals Hilton Head Island
- Rentals with a sauna Hilton Head Island
- Rentals with breakfast Hilton Head Island
- Rentals with lake access Hilton Head Island
- Beach apartment rentals Hilton Head Island
- Townhouse rentals Hilton Head Island
- Family-friendly rentals Hilton Head Island
- Rentals with an EV charger Hilton Head Island
- Waterfront rentals Hilton Head Island
- Rentals with a hot tub Hilton Head Island
- House rentals Hilton Head Island
- Rentals with outdoor seating Hilton Head Island
- Rentals with a fireplace Hilton Head Island
- Fitness-friendly rentals Hilton Head Island
- Flat rentals Hilton Head Island
- Rentals with a cinema Hilton Head Island
- Pet-friendly rentals Hilton Head Island
- Rentals with an accessible-height bed Hilton Head Island
- Rentals with an accessible-height toilet Hilton Head Island
- Luxury rentals Hilton Head Island
- Resort rentals Hilton Head Island
- Beachfront rentals Hilton Head Island
- Rentals with a washing machine and dryer Hilton Head Island
- Rentals with pools Hilton Head Island
- Savannah Historic District
- Coligny Beach Park
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- North Beach, Tybee Island
- Tybee Beach Pier and Pavilion
- Harbour Town Lighthouse
- Bonaventure Cemetery
- Edisto Beach State Park
- Wormsloe Historic Site
- Skidaway Island State Park
- Oatland Island Wildlife Center
- Jepson Center for the Arts
- Hunting Island State Park
- Shelter Cove Towne Centre
- Kiawah Beachwalker Park
- Fort Pulaski National Monument
- Cathedral of Saint John the Baptist
- Savannah College of Art and Design
- Seabrook Island Beach
- Owens-Thomas House
- Tybee Island Marine Science Center
- Tybee Island Light Station
- Things to do Hilton Head Island
- Tours Hilton Head Island
- Sightseeing Hilton Head Island
- Food and drink Hilton Head Island
- Art and culture Hilton Head Island
- Nature and outdoors Hilton Head Island
- Things to do Beaufort County
- Tours Beaufort County
- Nature and outdoors Beaufort County
- Food and drink Beaufort County
- Art and culture Beaufort County
- Sightseeing Beaufort County
- Things to do South Carolina
- Sports activities South Carolina
- Nature and outdoors South Carolina
- Art and culture South Carolina
- Entertainment South Carolina
- Sightseeing South Carolina
- Tours South Carolina
- Food and drink South Carolina
- Things to do United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Entertainment United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States