Holiday rentals in Hilton Head

5 out of 5 average rating, 53 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)

Villa in Hilton Head Island

5 out of 5 average rating, 8 reviews

New Listing! Penthouse Oceanfront Sea Cloisters Co

Relax and enjoy the best of Hilton Head from this oceanfront 3BR/3BA penthouse at Sea Cloisters. Located mid-island off Folly Field Road, this bright and spacious condo offers breathtaking ocean views, a fully stocked kitchen, and easy beach access just steps away. With two king bedrooms on the main level and a loft with one queen bed and one full bed, there’s plenty of room for families or groups of friends (sleeps 6 total). Enjoy the direct ocean view from the master bedroom, unwind in the co

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.

4.99 out of 5 average rating, 79 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!

A tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.

4.97 out of 5 average rating, 305 reviews

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!

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.

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.

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.

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

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.

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.

Flat in Hilton Head Island

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.

4.99 out of 5 average rating, 351 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.

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.

4.96 out of 5 average rating, 357 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! 💕

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.

4.99 out of 5 average rating, 195 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**

Superhost

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

Treehouse in Hilton Head Island

5 out of 5 average rating, 3 reviews

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.

Popular amenities for Hilton Head holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Hilton Head

Flat in Hilton Head Island

A spacious living area features comfortable seating arrangements, including a cozy sectional sofa and armchairs. Large glass doors provide access to the balcony, with views of the outdoors. The room is bright, complemented by a flat-screen TV and decorative shelving.

5 out of 5 average rating, 43 reviews

#4203 Renovated/1BR/2BA/Direct Ocean Views/Sofa Bd

A private residence is set among tall trees, featuring a spacious patio area with a circular pool at its center. A barbecue grill and poolside loungers are visible, surrounded by natural landscaping, creating a serene outdoor retreat.

4.95 out of 5 average rating, 38 reviews

Starfish Beach House with Pool and Bikes

The exterior of a charming villa is presented, featuring a light-colored facade and multiple balconies. A prominent sign reading 'Crown Reef at Port Royal' adds character to the landscape, while surrounding greenery and trees enhance the natural appeal of the setting.

4.98 out of 5 average rating, 47 reviews

Luxury Beach & Golf Villa - 5 min walk from Beach!

5 out of 5 average rating, 18 reviews

Beach Villa at Westin: Free Golf, Pickleball, Pool

An inviting open-concept living area features a dining table set for four, complemented by a soft rug beneath. A modern kitchen is visible in the background, with sleek cabinetry and appliances, while a comfortable seating area showcases a leather sofa and glass coffee table, illuminated by ceiling fans.

5 out of 5 average rating, 29 reviews

Luxurious, Dog Friendly Ground Fl Villa Fazio Golf

Island in Hilton Head Island

An open-concept living area features wooden floors and a high ceiling with exposed beams. Comfortable seating is arranged around a central island and a large dining table. Natural light fills the space through multiple windows, showcasing vibrant décor and an inviting atmosphere.

5 out of 5 average rating, 7 reviews

Netflix Featured Island Getaway: Old House Cay

A covered patio area features a heated swimming pool with clear water. A dining table with several chairs sits nearby, complemented by comfortable seating. The backdrop includes a tranquil body of water and charming buildings, creating a serene outdoor ambiance.

4.84 out of 5 average rating, 172 reviews

Luxe Family Gem-Heated Pool~Walk to Beach~Elevator

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.