Holiday rentals in Hilton Head
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Top-rated holiday rentals in Hilton Head
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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.
*New* Easy Breezy at Hilton Head Beach & Tennis
Newly renovated in March ‘26 and brand new,from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa - with all of the amenities needed to enjoy a relaxing stay at the Hilton Head Beach & Tennis resort. Our villa is located just steps from the only elevator in the building. Our resort offers the largest pool on the island, several restaurants, a large playground & picnic area, on site bike rental, 24 hour gated security, 8 lighted tennis courts, and 6 pickleball courts.
Ocean View! Remodeled! Steps to beach/Pool/Bar
FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!
98 Sandcastle Ct
98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.
Oceanfront Luxury! KING BED 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
Few mins walk to beach 1st flr pools hot tub pball
Ready for a beach vacation with a side of golf, pickleball and biking? Welcome to our newly renovated 1st floor villa in Fiddler's Cove. STR Permit# 24587. Our villa is a 6-7 minute walk to Folly Field beach with private beach access. THE best sunrises, just a few minutes away. Surrounded by world class golf courses and fantastic restaurants. Onsite amenities include 2 pools, a hot tub, racquetball, pickleball, tennis and gym. Pools open from March 1 - October 31 and hot tub open year round.
Oceanfront Luxury! KING BED Beach Bar & Pickleball
PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨See the Ocean Sunrise & Hear the Waves! ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball, Basketball, Volleyball 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 No Resort Fees! Beachfront Pool w/Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)
Luxury KING BED + 65"TV Beach Bar FREE Pickleball
✨Airbnb Top 5% Guest Favorite✨ Oceanfront Building BIG Ocean View from Balcony Steps to Beach Bar & Pool FREE Gym, Pickleball Tennis Volleyball & More! 100% NEW HGTV Designer Renovation! KING BED 75" & 65" SmartTVs Beach Chairs, Boogie Boards, Ice Chest & More Marble Kitchen/Spa Bath Top Floor WiFi 557 Mbps Elevator RESORT: No Resort Fees Huge Oceanfront Pool Tiki Beach Bar & Grille (Mid Feb-Nov) Sports Bar Bike Rental Gated 24/7 Security Free Island Trolley (Apr-Sept) 4 Beach Boardwalks
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.
Luxury 3-Bdrm HHI Art Loft Townhome
Located in the private Spanish Wells area of Hilton Head Island, one of the most sought after vacation destinations in the world. Eight minute drive to Hilton Head Island beaches, golf/tennis, restaurants, bars, bike trails, and countless shopping, entertainment, and outdoor exploration activities. Kick back and relax in this calm, stylish townhome with distinct spaces for everyone. Home Owners have appointed the home with original and collected art. Convenient to Savannah & Bluffton.
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! 💕
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**
Popular amenities for Hilton Head holiday rentals
Other great holiday rentals in Hilton Head
Luxury Beach & Golf Villa - 5 min walk from Beach!
3BR for 8 Golf & Beach Retreat @ Links 8B!
Sea Pines Home w Large Deck | Great for Couples!
Charming 3BR / 2 bath beach bungalow with hot tub!
Walk to Harbour Town: Airy Treehouse w/ Bikes
Luxe Family Gem-Heated Pool~Walk to Beach~Elevator
Pet friendly condo with amazing Broad Creek views
SeaPines - Private Beach Path, Private Pool, Bikes
Frequently Asked Questions
Where is Hilton Head located?
Hilton Head is an island town along the Atlantic coast of South Carolina, set within the Lowcountry region. It is known for sandy beaches, maritime forests, and coastal wetlands.
When is the best time to visit Hilton Head?
Late spring and early fall are often recommended for pleasantly warm weather and vibrant local events. Summer is popular for beach activities, while winter and early spring have cooler temperatures and lighter crowds.
How old is Hilton Head?
Communities on Hilton Head trace histories back thousands of years, with Indigenous peoples living on the island long before European exploration in the 1500s. Modern development expanded in the twentieth century, especially as it became a resort destination.
Why was Hilton Head built?
Initially, Hilton Head was settled for agriculture and trade, becoming known for crops produced on plantations. Its transformation into a resort area was guided by interest in coastal recreation, natural beauty, and the desire to preserve local ecology.
What are some things to do near Hilton Head?
Travelers can explore sandy beaches, wildlife preserves, and nature trails near Hilton Head. The area has golf courses, bike paths, and opportunities to experience local Gullah culture, waterfront dining, and art galleries.
How is the weather near Hilton Head?
Hilton Head has mild winters, with temperatures typically from 40–61°F (4–16°C), and warm summers around 74–92°F (23–34°C). Rainfall is more common in late spring and summer, so visitors often pack layered clothing and light rain gear.
How was Hilton Head built?
Hilton Head’s landscape was shaped by natural processes and later developed for agriculture, with plantation systems built and worked by enslaved labor. In the mid-twentieth century, thoughtful planning guided the transition to residential neighborhoods, resorts, and protected green spaces.
What is the history of Hilton Head?
Hilton Head holds histories shaped by Indigenous communities, European colonization, and plantation-era developments worked by enslaved Africans. The island has preserved Gullah heritage and played roles in the Civil War, evolving into a popular coastal destination.
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- Coligny Beach Park
- Savannah Historic District
- Forsyth Park
- Harbour Town Golf Links
- Hunting Island State Park Beach
- North Beach, Tybee Island
- Tybee Beach Pier and Pavilion
- Angel Oak Tree
- Bonaventure Cemetery
- Harbour Town Lighthouse
- Wormsloe Historic Site
- Shelter Cove Towne Centre
- Edisto Beach State Park
- Hunting Island State Park
- Skidaway Island State Park
- Oatland Island Wildlife Center
- Cathedral of Saint John the Baptist
- Jepson Center for the Arts
- Savannah College of Art and Design
- Fort Pulaski National Monument
- Kiawah Beachwalker Park
- Seabrook Island Beach
- Owens-Thomas House
- Tybee Island Light Station