Holiday rentals in Hilton Head

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Top-rated holiday rentals in Hilton Head

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Guest favourite
Apartment in Hilton Head Island
4.96 out of 5 average rating, 55 reviews

Oceanfront Luxury! KING BED Beach Bar + Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨ Ocean Sunrise / Hear the Waves ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball HGTV Decorator Renovation KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM WiFi 515 Mbps Coastal Décor TOP FLOOR w/Elevator Couples Escape! Beach Chairs, Boogie Boards, Ice Chest & More! RESORT No Resort Fees Beachfront Pool w/Tiki Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)

Guest favourite
A dining table is set for four, featuring blue and white dishware and glassware. A comfortable living area showcases a sectional couch, two accent chairs, and a large TV mounted on the wall. Natural light filters in through glass doors, leading to an outdoor space.
Townhouse in Hilton Head Island
5 out of 5 average rating, 14 reviews

Folly Fun! Permit # 076134

Enjoy a quiet and relaxing 2 bedroom 2 1/2 bath condo just a Stone's Throw from Folly Field Beach. Conveniently located near several shopping plazas, you will find everything you need for your stay. If cooking is your thing, a gas grill and new appliances compliment a fully stocked kitchen. You can take a short walk to the beach or just lounge by the community pool. 4 beach chairs, 4 beach towels, a beach umbrella and beach wagon are also available for your use. Just bring your bathing suit!

Top guest favourite
A private balcony overlooks a pool surrounded by lounge chairs and lush greenery. The ocean is visible in the distance, framed by tall trees under a clear blue sky. The space includes a small round table with two chairs.
Apartment in Hilton Head Island
4.9 out of 5 average rating, 173 reviews

⭐Direct Oceanfront Villa Steps to Beach w/ Pool⭐

Welcome to Ocean Pearl Villa. Sit back, relax and listen to the crashing of the waves, while relaxing on your private balcony of our two bedroom, two bath beautiful oceanfront condo. Ocean Pearl is located in Beachwood Place, a 24 unit gated private complex, on Hilton Heads finest South Forest Beach & only 3 minute walk to Coligny Plaza, the heart of Hilton Head's restaurants, Shopping & family activities. You will enjoy the wonderful accommodations and spectacular views at 2H Beachwood Place.

Top guest favourite
The image captures a private heated pool beneath a covered patio. Comfortable lounge chairs surround the pool, and an outdoor dining area features a large table with chairs. A shaded umbrella stands above the table, while greenery and a grill are visible, enhancing the outdoor setting.
Home in Hilton Head Island
5 out of 5 average rating, 117 reviews

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.

Top guest favourite
A bright dining area offers a view of the ocean through open doors leading to a private beachfront balcony. Coastal décor is present on the round table, complemented by neutral tones and natural light streaming in from the outdoors.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 354 reviews

Oceanfront KING BED 65"TV Beach Bar Pickleball GYM

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

Top guest favourite
A renovated kitchen features modern stainless steel appliances including a microwave, oven, and dishwasher. White cabinetry and granite countertops create a clean aesthetic. Ample storage is provided by drawers and cabinets, while laminate flooring adds a warm touch to the space.
Apartment in Hilton Head Island
4.99 out of 5 average rating, 223 reviews

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.

Top guest favourite
A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 217 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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**

Guest favourite
Apartment in Hilton Head Island
4.85 out of 5 average rating, 47 reviews

Beachfront Bliss: 1BR Villa at Admiral's Row

Retreat to an oceanfront haven where the Atlantic is your backyard. This Admiral’s Row villa offers a bright, coastal interior designed for relaxation. Guests enjoy premier resort amenities, including the largest pool on Hilton Head, basketball courts, and a playground. Perfectly situated near world-class golf and waterfront dining like Hudson’s, this villa combines the privacy of a condo with the excitement of a full-scale resort. Book now to catch the next sunrise over the waves.

Superhost
Apartment in Hilton Head Island
4.8 out of 5 average rating, 179 reviews

Beach Front Villa Oak Tree Lined Views to Water

3 Min Walk to the Beach - Your personal paradise awaits! Whether you’re visiting for a weekend getaway or a long-term snowbird retreat, this beautiful beachfront villa is sure to please. You’ll stay just steps from the beach and enjoy lagoon views and amenities this quiet gated community offers, including 24-hour security, pools, a sauna, tennis, and more! 3 Min Walk to the Beach 3 Min Drive to Hilton Head Distillery 12 Min Drive to Shelter Cove Harbor

Superhost
The living area features a spacious brown leather sofa and a coffee table placed on a patterned rug. A kitchen island with three high stools is visible, along with modern appliances in a sleek kitchen. A ceiling fan is installed above for air circulation.
Apartment in Hilton Head Island
4.82 out of 5 average rating, 55 reviews

Stunning Condo 4U - Beach & Pool Getaway - King Bd

Hilton Head Island Beach and Tennis Resort along Folly Field Beach; a Beachfront Oceanside Resort. Resort has direct Beach Access. No need to get in a car or ride a bike to the beach!! Beach Comfort & Gorgeous 1-Bedroom Condo This villa is in Building 'B'...(#B-209) 2nd Floor ...100 yards to the Islands largest pool and extra wide Island Beach. FULLY REMODELED ! King Bed coming June 28th!!! (photos will depict Queen until we can update photos)

Top guest favourite
Apartment in Hilton Head Island
4.95 out of 5 average rating, 21 reviews

Steps to Beach, Water Views, 3 Pools & Hot Tub

Escape the crowds and discover the "quiet side" of Hilton Head. Our freshly renovated (Oct 2025) second-floor end unit offers a rare dual-view experience: watch the sunrise over the Atlantic (peek-a-boo view) and the calm lagoon right from your private screened porch. Whether you’re here for a romantic retreat or a family adventure, you’ll enjoy a bright, coastal-chic sanctuary just steps from the pristine shores of the Port Royal Sound.

Top guest favourite
Apartment in Hilton Head Island
4.94 out of 5 average rating, 144 reviews

Subtropical Stunner-King bed & bikes! Central Air!

Wake up to breathtaking ocean views in this beautifully renovated 3rd-floor villa, the perfect escape for two. Enjoy an open-concept design with a plush King bed, cozy Queen sleeper, a fully equipped modern kitchen, and a spa-style walk-in shower. Sip coffee on your private balcony, stroll the beach just steps away, or bike to nearby shops and restaurants — beach chairs and bikes included for your adventure.

Popular amenities for Hilton Head holiday rentals

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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