Holiday rentals in Hilton Head Island

A bright living area features a light-colored sofa with a navy throw blanket. A glass coffee table stands on a patterned rug, while a tall lamp provides additional lighting. Art prints are displayed on the wall, and a balcony extends into the greenery beyond.

4.9 out of 5 average rating, 116 reviews

Modern Villa, Walk to Beach & Coligny Plaza

Don’t miss this modern-coastal 2 bedroom, 2.5 bath villa right in the heart of Hilton Head, making it the ultimate beach getaway! Walk into an open concept, 2-story villa with a balcony overlooking lush palmetto trees. Cool off and relax in one of the 2 on-site swimming pools. Just a 7 minute walk to the beach and newly developed Lowcountry Celebration Park & Playground. Also a 10 minute walk to Coligny Plaza’s shops and restaurants! The possibilities are endless during your time on the island.

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, 334 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! 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 candle is displayed on a table, surrounded by seashells, with a sunset view of the ocean in the background. The warm colors of the sky reflect off the water, while a cup is placed nearby, adding to the serene atmosphere of the balcony.

4.99 out of 5 average rating, 102 reviews

Luxury OceanView KING BED 75"TV Bar Gym Pickleball

✨Top 5% Airbnb Home✨ BIG OCEAN VIEWS FROM LIVING ROOM & BALCONY! Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar! FREE Pickleball, Tennis, Gym & More HGTV Featured Decorator 100% NEW Luxury renovation KING BED + 75" & 65" Smart TVs Expanded Bedroom Luxe Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley Stop

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, 291 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!

Home in Hilton Head Island

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, 104 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 light-filled living area features a white sofa complemented by a blue accent chair. A decorative table with a tray of flowers and a plush area rug enhances the space. Large glass doors open to a balcony, offering expansive views of the ocean.

4.98 out of 5 average rating, 159 reviews

My Blue Heaven, Direct Ocean Front View

Welcome to our ocean front rental, a haven for couples seeking a romantic and stylish getaway. With its breathtaking ocean view, five-star reviews, and recent remodel in 2023, this rental promises an unforgettable experience. Our guests have praised the attention to detail, the stunning view, and the overall ambiance of the space. Rest assured that your stay will be nothing short of extraordinary. Step out onto the balcony and take in the fresh sea breeze as you relax in the swinging chair.

Flat in Hilton Head Island

Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.

4.83 out of 5 average rating, 186 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

This 2nd floor villa has breathtaking, unobstructed ocean views from the living room and master bedroom. Walk to Coligny! Two bedroom suites (new mattresses and ceiling fans), with separate renovated baths. Beautiful maple hardwood & tile floors throughout. Fully appointed kitchen boasts granite countertops, maple cabinets, and stainless steel appliances. New Washer/Dryer. Jim Says "I personally stay in each of my units to ensure they are maintained to my highest level of expectations."

4.99 out of 5 average rating, 664 reviews

A well-lit living area features a comfortable sofa and a patterned armchair, surrounded by large windows allowing natural light. A coffee table holds magazines and a decorative tray, while plants add a touch of greenery. The kitchenette is visible in the background, enhancing the open layout.

Guest house in Bluffton

Lowcountry Retreat Carriage House

Located in a quiet neighborhood, minutes from Old Town Bluffton, where you can find unique shops, art galleries, & great places to eat - many with live music! A stroll through the neighborhood will take you past a local park with playground, workout area, & walking paths. There are many ponds to enjoy the local wildlife, wetland areas, and beautiful oak trees. It's so peaceful! Convenient to Hilton Head, Beaufort, and Savannah, it's the perfect spot for exploring, shopping, or relaxing!

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.

5 out of 5 average rating, 336 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.

Villa in Hilton Head Island

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.

4.96 out of 5 average rating, 107 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.

A sunlit living space features a navy blue sofa and an elegant dining table surrounded by four chairs. Large sliding glass doors provide access to the oceanfront balcony, where views of the beach and coastal landscape can be seen in the distance.

4.98 out of 5 average rating, 205 reviews

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨Airbnb top 1% Home ✨ Oceanfront Balcony 100% New Luxury Renovation HGTV Featured Decorator KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR w/Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT Beachfront Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball 2nd Pool Bike Rental Gated w/24 Hour Security Free Trolley Stop Bradley Beach

Guest house in Hilton Head Island

A combined living and sleeping area features a gray couch with decorative pillows, a small coffee table, and a light-colored area rug. A twin bed with a white quilt and pillows is visible in the background, with large windows draped in yellow curtains allowing natural light to enter.

4.92 out of 5 average rating, 256 reviews

Alli B's Air B and B-Great Country access off 278

Your family will be close to everything when you stay at this centrally-located place. No gate fees or parking fees- right off of 278- central located between Bluffton and HHI under foot of bridge. Farm like experience -family owned 30 years . Quiet . Pet friendly . Beds-two twin -can pull together if wish -one couch(Not a sofa bed) and one mattress under a bed that can be moved out . Property has several buildings , Guest apt is above garage. NOTE: SEE Space info below

Popular amenities for Hilton Head Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Hilton Head Island

4.98 out of 5 average rating, 40 reviews

Apartment in Sea Pines

Sea Pines Condo, 2 Bdrm/2Ba w/Bikes! Pets welcome!

Flat in Hilton Head Island

A vibrant sunrise is captured over the Atlantic Ocean, with the sun rising above the horizon. Silhouetted palm trees in the foreground create a contrast against the warm hues of orange and red in the sky, reflecting the tranquility of the scene.

4.88 out of 5 average rating, 34 reviews

Oceanfront Villa-Great Spring and Summer Prices!

5 out of 5 average rating, 19 reviews

Home in Sea Pines

Sea Pines Home w Large Deck | Great for Couples!

Superhost

A private backyard scene features a newly designed pool with a surrounding deck, complemented by tropical plants. The spacious home showcases large windows allowing natural light to flood the interior, with a patio area providing outdoor seating near the pool.

Home in Palmetto Dunes

5 out of 5 average rating, 7 reviews

Extravagant Hilton Head Luxury Home Private Pool

Villa in Hilton Head Island

An expansive balcony features a cushioned sofa and side chairs, centered around a wooden coffee table. A glass-topped dining table is positioned nearby, suitable for outdoor meals. Light-colored flooring provides a pleasant contrast to the wooden railings and surrounding greenery.

4.9 out of 5 average rating, 41 reviews

Walk to the Beach! Coastal Villa w Large Balcony!

4.91 out of 5 average rating, 79 reviews

A colorful dining area features sturdy wooden tables and benches, set beneath a shaded canopy. Tropical palm trees and a sandy path leading to the beach can be seen in the background, providing a relaxed atmosphere for guests.

Home in Palmetto Dunes

Apartment in Hilton head resort

5 out of 5 average rating, 23 reviews

Home in Sea Pines

Sea Pines hut, 5-min walk to beach, dog friendly.

A welcoming living area is presented, featuring a comfortable sofa and a round dining table with two chairs. A wall-mounted television is visible. Natural light floods in through sliding glass doors, offering a view of palm trees and outdoor seating.