House holiday rentals in Hilton Head Island

The charming cottage features a low country style exterior with reclaimed wood siding and a corrugated metal roof. A welcoming front porch is adorned with seating. Surrounding landscaping includes shrubs and trees, enhancing the serene setting within the historic district.

4.99 out of 5 average rating, 386 reviews

Bluffton Farm Cottage: Come for the Holidays

(STR21-00116) Located in the Old Town Bluffton Historic District, our charming cottage is a short walk from art galleries, boutiques, gift shops, restaurants, parks, historic houses, and the May River. Hilton Head Island beaches and bike trails, dozens of golf courses, two National Wildlife Refuges, a variety of coastal/ocean opportunities, and many outdoor activities are nearby. Only 35 minutes from Savannah, the cottage is ideal place for couples trips, friends getaways, or family vacations.

A charming beach cottage is framed by mature trees and lush landscaping. A pathway of gravel leads to the entrance, featuring a well-maintained lawn. An American flag is displayed prominently, enhancing the welcoming atmosphere of the exterior.

5 out of 5 average rating, 50 reviews

Curlew Cottage steps to sand & shops. NFL Ticket!

Welcome to Curlew Cottage! This beautifully renovated 50's beach house is a rare find. It is nestled 4 houses from the beach in a canopy of trees with a large screened porch for outdoor living. The cottage is 2 blocks north of Coligny Plaza, with many dining options, live music and hundreds of shops. It is 80 steps to the pristine sands of the Atlantic Ocean through a beach access shared by only 10 homes, so close to everything but away from the crowds! One dog is allowed on a case by case basis

A private balcony features blue Adirondack chairs arranged around a metal table, overlooking a natural lagoon surrounded by lush green foliage. Sunlight filters through the trees, enhancing the peaceful ambiance of the outdoor space.

4.97 out of 5 average rating, 72 reviews

Sea Pines Home! Walk to Beach | Lagoon View & Pool

✨Top 5% of Homes on Airbnb✨ "ISLAND LIFE" is a charming 3/2 Sea Pines Bungalow - a short walk to the beach/next to neighborhood pool! Nestled just inside the Ocean Gate, this retreat stands alone on an oversized wooded lot! Enjoy a private balcony that overlooks a large, natural lagoon that is teeming with wildlife! ● Short Walk or Bike to Beach! ● 3 bedrooms / 2 bath ● Private Home - Big Wooded Lot ● On Wildlife Lagoon ● Next to Pool ● Family Friendly ● 4 SmartTVs ● PS4 ● Beach Gear Provided

5 out of 5 average rating, 12 reviews

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

Location; location; location! Awaken your senses in this cottage surrounded by natural beauty of pines, pond, and blue herons. 5 min walk to Sea Pines pristine beach. 2-mile bike to the beach club and Nature Reserve full of wildlife. Luxurious interior and cozy outdoor porch, plush king bed, queen sofa bed sleep 4. cathedral ceiling, dog friendly, free bikes, beach chairs and cart, perfect for couples, solo travelers, or small families looking to create a luxurious Hilton Head Island experience.

A two-story house features a light-colored exterior with a metal roof and a front balcony. The driveway provides access to two garages, with landscaped greenery and grass surrounding the property, enhancing the overall curb appeal.

4.86 out of 5 average rating, 376 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

✔wlk to beach 500 yrds, bike, boat, tennis, golf ✔pet-ok✔5beds✔gourmet kitchen☼sundeck✔ping pong table &games✔screened outdoor area with grill&table✔Spectrum&AppleTV*Roku&WiFi✔W&D✔Busn traveler ready✔2 garages✔private yard space✔1st-floor kitchen, living room with love seat and cal king sofa✔semi-open sitting room aka bdrm with cal king sofa, adjacent small closet, powder room✔sun porch✔2nd floor 2 bdrms with a queen✔master bdrm with king bed Tempurpedic, wlk-in cl and bath with ♥♥shower, 2Z AC

A spacious living room features vaulted ceilings and a ceiling fan. Two leather sofas face a wooden coffee table, with a decorative bowl in the center. A 55-inch Smart TV is mounted above a modern fireplace, and large glass sliding doors provide natural light and access to the backyard.

4.99 out of 5 average rating, 135 reviews

“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops

Privately-owned 2000 SF one-level home sits on a wooded corner lot conveniently located inside the entrance of Sea Pines Resort. This 3 BR, 2BA home was extensively renovated in August 2020, with inviting French-inspired coastal decor for a relaxing cozy feel. "Sea La Vie" chalet is within walking distance to grocery stores, shops, and restaurants. A short drive or bike ride takes you to the private Beach Club, housing oceanfront dining and bar, upscale facilities, and wide beaches. Bienvenue!

A private pool area is framed by lush greenery and palm trees, featuring a turquoise swimming pool with a pink float. Two sun loungers are positioned beside the pool, with a shaded cabana offering seating and a dining area.

4.98 out of 5 average rating, 121 reviews

Resort-Style Pool, Cute House 88 Steps to Sand

Experience the best of island life in a resort-style setting. Recently renovated, this classic home offers comfortable living by a MAGNIFICENT beach for a memorable family-friends getaway. 1st floor features a screened in porch; open living-dining area; a well-stocked kitchen; three bedrooms (3rd bedroom with separate hallway) and two bathrooms. The new private pool space is where you can expect additional relaxation around pool, cabana with dining area, KitchenAid grill and outdoor seating.

4.95 out of 5 average rating, 125 reviews

A spacious living area is accentuated by vaulted ceilings and large windows, allowing natural light to fill the room. Comfortable sofas are arranged around a central coffee table, with decorative cushions adding color. A lamp and a decorative vase create a welcoming ambiance in this inviting space.

Home in Palmetto Dunes

Lovely 3BR in Palmetto Dunes w/ new pool & spa

Lovely 3 BR home on #2 tee of the Fazio golf course in Palmetto Dunes Resort. Near tennis/pickleball center, general store, & restaurants. Newer pool and spa. Quartz countertops. Two King BRs, 3rd BR with 2 Queens. Flat screen TVs, cable, ROKU in all BRs. Doorbell cam at front door porch with recording capability for host/guest safety. Beach access @ Omni resort and the Dunes House a 5-10 min ride by bike or 15 min walk. Beach towels/umbrellas/chairs not provided. Pool/spa heat for extra fee.

The front exterior of the house features a welcoming porch with a central decorative door and flanking windows. Flowering plants are suspended from the eaves, while well-maintained shrubs frame the entrance. A clear pathway leads to the door, inviting guests into the home.

4.96 out of 5 average rating, 127 reviews

Encanto of the Lowcountry in Old Town Bluffton

Welcome to the Heart of the Lowcountry - Bluffton South Carolina! Come stay in this vibrant & luxurious 2 BED / 2 BATH recently renovated home and enjoy the coastal way of life with cool river breezes as you discover the hub of businesses, shopping and community gatherings of eclectic Old Town. Spend time in the sun and sand on the nearby beaches of Hilton Head Island or visit the downtown waterfront of Historic Beaufort. Lots of local fun & activities! Welcome to Encanto of the Lowcountry.

An outdoor relaxation area features a heated pool surrounded by lounge chairs. Two cushioned armchairs with decorative pillows are positioned beside a small table near a hot tub, all set against a backdrop of lush greenery and tall trees.

5 out of 5 average rating, 65 reviews

Walk to Beach-Amazing New Home-Hot Tub-Heated Pool

Maximum 16 guests. Welcome to Sea Mist Manor-A quick walk to one of Hilton Head Islands best beaches.. Our family has created an amazing ocean getaway. Featuring upscale furnishings & decor from local shops. Creature comforts include-high end hot tub-infra red sauna-arcade-fun kids room-golf themed room.. We welcome you with open arms to Sea Mist Manor-A Seaside Extravaganza! As seasoned hosts, achieving 6+yrs of Airbnb Super Host status, rest assured you're in good hands.

The exterior of a two-story villa features a light-colored facade and a welcoming entrance with steps leading to the front door. Lush greenery lines the path, with manicured shrubs and palm trees enhancing the natural setting. Large windows are present throughout the structure.

5 out of 5 average rating, 46 reviews

The Caddyshack - Perfect Location!

Welcome to The Caddyshack! Centrally located in Shipyard, this fully renovated 2 bedroom 2.5 bath villa overlooks the tee box on the 3rd hole of the Brigatine golf course. Watch the day's last golfers go by while the sun's final rays set from the back porch. Enjoy the many miles of walking/biking trails, the nearby Shipyard Beach Club, Coligny Plaza shops & restaurants, golf and more. The Caddyshack has been recently renovated and is ready for you. Join us soon!

5 out of 5 average rating, 70 reviews

Sea Pines house ~ Golf Sim / Putting Green / Games

Centrally located in HHI 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 & lounging areas, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 king beds and 4 double beds), 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 Hilton Head Island.

Popular amenities for house rentals in Hilton Head Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 121 reviews

An inviting living space features a sectional sofa, a wooden coffee table, and a dining area with several chairs. Natural light illuminates the room through multiple windows, highlighting the coastal-inspired decor and airy layout. A chandelier complements the open, relaxed atmosphere.

Home in Palmetto Dunes

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

A serene pool area is surrounded by lush greenery, featuring a spacious swimming pool with lounge chairs nearby. Colorful umbrellas provide shade, and a stone patio extends around the pool, inviting relaxation and outdoor enjoyment.

4.98 out of 5 average rating, 52 reviews

Sea Pines - S. Beach Charmer - Private Pool/Spa

A serene lagoon scene is presented, featuring calm water bordered by leafy trees. Palm trees stand prominently in the foreground, while charming homes line the water's edge under a clear blue sky, providing a tranquil backdrop.

4.92 out of 5 average rating, 73 reviews

Updated! Sea Pines Lagoon View Oasis

A pristine pool area is surrounded by lush greenery, featuring a spacious pool and a relaxing spa. Poolside seating includes turquoise chairs and an umbrella. A dining table with outdoor chairs is situated nearby, all on a textured stone patio.

4.98 out of 5 average rating, 103 reviews

Private pool/spa : pool heat available : Kg master

A light-filled living area showcases a spacious sectional sofa accented with patterned cushions. A wooden coffee table sits in front, complemented by a contemporary chair. Large windows surround the room, offering views of the surrounding greenery, while a flat-screen TV is mounted on a white entertainment unit.

4.83 out of 5 average rating, 40 reviews

The Ocean Lily of Sea Pines

The outdoor area features a private pool with a cozy seating arrangement nearby. A fire pit with glowing embers is central to the setting, surrounded by large loungers and a dining table. A large umbrella shades the outdoor seating, while a whimsical inflatable swan floats in the water.

5 out of 5 average rating, 27 reviews

Marsh Views | Pool, HotTub, Game Room&Pet Friendly

A shaded outdoor patio area is furnished with a large table and comfortable chairs. A green umbrella provides protection from the sun, while lush trees and a well-manicured landscape create a serene view of the golf course in the background.

5 out of 5 average rating, 31 reviews

Brand New Sea Pines Remodel - Minutes To Beach!

A cozy screened-in porch is displayed with four Adirondack chairs surrounding a glass-topped table. A vibrant blue area rug features a leaf pattern, while large glass windows provide expansive views of the tidal marsh and lush greenery outside.

4.9 out of 5 average rating, 20 reviews

Lagoon & Tidal Marsh Views w/Screened-In Porch

Weekly house rentals

A woman stands alone on a wide, sandy beach, gazing toward the calm ocean. In the distance, a couple is seated under a blue umbrella. The sky is overcast, creating a serene atmosphere over the expansive shoreline.

4.97 out of 5 average rating, 77 reviews

Sandfiddler Cottage ~ Seapines ~ Hilton Head

A screened pool area showcases a serene blue swimming pool, framed by large glass doors offering views of the surrounding greenery. Relaxing lounge chairs are positioned nearby, and natural light floods the space, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 15 reviews

27 Kingston: Spacious Shipyard Home, Private Scree

Superhost

A private pool area is surrounded by lush greenery, featuring a rectangular pool with a wading area and lounge chairs. Two red Adirondack chairs are positioned nearby, along with a large umbrella for shade. Palm trees further enhance the serene outdoor space.

4.7 out of 5 average rating, 10 reviews

Newly Updated Home. Private Pool. Steps to

An outdoor space features a newly installed pool surrounded by lounge chairs and a dining area. A putting green, marked with golf holes, lies nearby. The home is set against a backdrop of tall trees, creating a serene environment.

4.87 out of 5 average rating, 45 reviews

Heels in the Sand- Private Pool & Putting Green

A dining area features a reclaimed wood table surrounded by cross-back chairs. A shelving unit holds decorative items and books. Natural light brightens the stylish living room in the background, where plush seating and tasteful decor can be seen.

5 out of 5 average rating, 23 reviews

Steps to the Beach - Perfect All-Season Getaway

A welcoming living area showcases a comfortable gray sofa adorned with decorative pillows. A light wood coffee table is positioned in front, while a casual chair and a dining table with high stools are visible. Soft, natural light floods the space, enhancing the inviting ambiance.

4.89 out of 5 average rating, 37 reviews

NEW! Excellent Remodeled Best Beach & Tennis Villa

The exterior of The Yellow Cottage is showcased with a welcoming front porch framed by palm trees and landscaped greenery. A gentle pink sky serves as a backdrop, accentuating the cottage's charming architectural features and inviting ambiance.

4.99 out of 5 average rating, 78 reviews

Old Town Bluffton 'The Yellow Cottage' w Golf Cart

The exterior of a multi-story villa showcases a well-maintained structure with multiple balconies and walkways. Lush greenery and landscaping are visible along the pathway, leading to the entrance. A blue vehicle is parked nearby, and a clear sky is seen above.

4.88 out of 5 average rating, 8 reviews

3bd/3ba -Ocean Palms & Westin access & daily golf

Private house rentals

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.

5 out of 5 average rating, 27 reviews

Starfish Beach House with Pool and Bikes

The spacious living area features high ceilings and a fan above. A soft gray sofa is positioned beside a coffee table with decorative items. The wall is adorned with a large flat-screen TV, and a fireplace adds a focal point. Large windows allow natural light to fill the space.

4.98 out of 5 average rating, 42 reviews

Sea Pines Home - Family Friendly, Great location!

A serene outdoor space is featured, showcasing a swimming pool surrounded by lounging chairs. The deck overlooks a tidal marsh with natural greenery and distant power lines visible. Soft blue and green cushions add a touch of color to the neutral-toned furniture.

4.93 out of 5 average rating, 28 reviews

(14) Views, Pool, Shuffleboard, Ping Pong

An open concept living area showcases wood-paneled ceilings and large windows, allowing natural light to fill the space. A sectional couch faces a TV, while a wooden dining table is set for meals. Sliding glass doors open to views of the backyard.

4.98 out of 5 average rating, 49 reviews

Sea Pines Villa - Walk to Beach, Golf and Tennis

A blue exterior of a house is framed by tall palm trees and lush greenery. A wooden deck with seating is visible, offering a welcoming outdoor space. The surrounding landscape features well-maintained shrubs, contributing to a calm and natural ambiance.

5 out of 5 average rating, 64 reviews

A WAVE FROM IT ALL! Rest, Relax, Recharge!

A light-colored two-story house is surrounded by lush greenery, featuring a welcoming entryway with a covered porch. Large windows allow for ample natural light, and decorative landscaping enhances the exterior appeal.

5 out of 5 average rating, 23 reviews

Old Town Bluffton Getaway

5 out of 5 average rating, 17 reviews

An open-concept living area is shown with stylish wood-style flooring. A comfortable sofa faces a large dining table with light-colored chairs. A well-equipped kitchen is visible in the background, featuring modern appliances. Ample lighting enhances the welcoming ambiance throughout the space.

Home in Palmetto Dunes

Palmetto Dunes Renovated Villa

Superhost

The outdoor space features a well-lit pool area surrounded by spacious brick-laid patio and green grass. The pool includes a spa and lounge chairs, set against a two-story brick home with illuminated windows, creating a welcoming ambiance.