House holiday rentals in Hilton Head Island

4.99 out of 5 average rating, 387 reviews

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.

Home in Bluffton

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

The spacious backyard features a large heated sports pool surrounded by a well-manicured lawn. Deck chairs in vibrant colors are arranged along the poolside, while a covered deck is accessible from the house. Lush trees provide shade, enhancing the relaxing outdoor environment.

5 out of 5 average rating, 19 reviews

Sweet Carolina~Pool~Fenced Yard~FirePit

Located in the prestigious Sea Pines Resort, Sweet Carolina Retreat has the amenities needed for that perfect beach vacation. This home has the rare combination of a spacious outdoor oasis along with a large fenced back yard with grass for 2 or 4 legged guests. Relax in the large sports pool or hot tub, and gather with your guests around the fire pit or outdoor bar. All of this is walking distance to the beach and an easy bike ride to Harbour Town (lighthouse) and South Beach Marina (Salty Dog).

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, 377 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.

4.99 out of 5 average rating, 235 reviews

A serene bedroom is presented with a light color palette. A spacious bed adorned with soft blue pillows is positioned in front of a large window with white blinds. A wooden bench sits at the foot of the bed, featuring neatly arranged towels. A side table with lamps and a decorative piece enhances the inviting space.

Home in Bluffton

Old Town Bluffton Home + Golf Cart No Cleaning Fee

This is Bluffton Living at its finest! This luxurious southern coastal home is located in the heart of Old Town Bluffton just a couple blocks from the Promenade & includes a new Golf Cart at no additional charge. Master is on the main floor. Walking distance to wonderful local hot spots including the coffee shops, wine bar, high end/casual restaurants, and charming boutiques. Our home has it all w/ a full kitchen w/ stainless steel appliances, Traeger grill, dishwasher, washer/dryer, & More!

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.

4.83 out of 5 average rating, 161 reviews

Luxe Family Gem-FREE Heated Pool~Walk to Beach~BBQ

Step into the spacious and fun 6BR 4Bath family oasis nestled in a tranquil neighborhood just a few steps away from pristine sandy beaches, restaurants, and exciting attractions. Explore the island from this prime location or lounge the day away next to the luxury swimming pool. ✔ 6 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Patio (Heated Pool, Fire Pit, BBQ) ✔ Deck ✔ Games (Beer Pong, Cornhole) Arcade ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Beach Accessories ✔ Parking See more below!

5 out of 5 average rating, 151 reviews

The exterior of a charming cottage is highlighted by vibrant string lights illuminating the porch and expansive windows. Large beams support the peaked roof, while surrounding trees create a natural, serene setting. A fish symbol decorates the entrance, welcoming guests to the tranquil retreat.

Home in Daufuskie Island

Glenn's Greenish Daufuskie Cottage

STR-007307-2025 Perfect get away on Daufuskie Island, SC with a view of the Inner coastal Waterway. Rent a golf cart, private quiet beaches and get away from it all. This cottage is great for families, workshops, reunions and retreats. Beautiful sunset views. The island is only accessible by ferry or boat. Beautiful views. Marshside Seashell Labyrinth directly across. You must rent a golf cart You for sure want to bring your bug spray of choice. wiki.officialdaufuskie

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!

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

The brand new remodel at "The Pines" is complete! This stunning getaway is located in Greenwood Forest and offers a modern coastal vibe with 3 bedrooms and 3 bathrooms. "The Pines" also boasts an open floor plan with two Master suites. You’re going to love the location right on the 5th green and 6th tee of Harbour Town Golf Links, where you and your guests will also soak in the breathtaking Carolina sunsets right from the expansive back deck!

Popular amenities for Hilton Head Island house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.85 out of 5 average rating, 142 reviews

An outdoor deck features a shapely pool surrounded by lounging chairs. Lush greenery and palm trees are visible in the background, offering a view of the golf course. A purple umbrella stands next to the pool, providing shade.

Home in Palmetto Dunes

Palmetto Dunes Home on 1st Tee Fazio Golf Course

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

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 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 spacious outdoor pool area features lounge chairs arranged around a large swimming pool, with several guests enjoying the water. Two hot tubs are visible nearby, surrounded by palm trees and blue umbrellas. The ocean can be seen beyond the pool, creating a serene backdrop.

5 out of 5 average rating, 18 reviews

Oceanfront condo with elevator and gated entrance!

A shaded balcony is furnished with two woven chairs and a small table, complemented by a decorative area rug. Lush greenery is visible beyond the railing, providing a natural backdrop, while large windows allow for ample light to fill the space.

4.98 out of 5 average rating, 120 reviews

Cozy beach house w/Private Heated Pool near park

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, 21 reviews

Lagoon & Tidal Marsh Views w/Screened-In Porch

A pool area is framed by lush palm trees, with an inground pool featuring step-like edges. Loungers are positioned alongside, and a blue umbrella offers shade. Beyond the pool, a sandy beach is visible, merging with the horizon under a clear blue sky.

4.93 out of 5 average rating, 14 reviews

109 Dune Lane - Oceanfront Paradise

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 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 living room displays a light, airy ambiance with large sliding glass doors leading to a private balcony. A plush couch is complemented by decorative pillows, and a patterned ottoman adds texture. Natural light filters through the windows, enhancing the inviting atmosphere.

4.84 out of 5 average rating, 58 reviews

~Couples Paradise~Villa W/Pool~Beachfront Resort

5 out of 5 average rating, 3 reviews

Luxury Sea Pines Home, Lagoon Views on Hilton Head

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!

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 serene view of a calm lake reflects surrounding trees and a building, creating a peaceful atmosphere. The shoreline is lined with pine needles, and the sight is illuminated by natural sunlight, showcasing the area's tranquility.

5 out of 5 average rating, 8 reviews

2 bd Ocean Palms Villa @ Westin property with golf

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.

4.93 out of 5 average rating, 30 reviews

Private Pool/Spa | Golf | Exq. Coffee | Seascape

Private house rentals

A charming, single-story home is nestled among tall trees, featuring a light green exterior. Flower pots adorn the front entrance, and a welcoming pathway leads to the door. The lush yard is bordered by greenery, enhancing the tranquil setting of the property.

5 out of 5 average rating, 17 reviews

100 5-star reviews don’t lie. ;)+Dog-friendly!

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

A clear, inviting pool is surrounded by a spacious patio, featuring tropical landscaping and comfortable seating. The home's large glass windows provide a view of the wooded area beyond, while a deck with shaded seating is visible in the background.

4.9 out of 5 average rating, 67 reviews

Private [Heated] Pool on Golf Course Mins to Ocean

The living area features an open layout with a cozy sofa and patterned armchairs surrounding a wooden coffee table. Natural light streams through large sliding glass doors that provide a view of the pool and outdoor seating area. Neutral tones and decorative accents create a welcoming environment.

4.89 out of 5 average rating, 35 reviews

Modern Serenity - Steps to Beach and Coligny Plaza

The spacious kitchen features modern cabinetry and large islands topped with elegant marble. Three pendant lights hang above the central island, while high-end appliances are positioned throughout. A stylish dining area is visible, creating a functional yet inviting cooking space.

4.79 out of 5 average rating, 24 reviews

Coastal Bliss

4.97 out of 5 average rating, 79 reviews

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.

Home in Bluffton

Old Town Bluffton 'The Yellow Cottage' w Golf Cart

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

A modern home with a unique architectural design sits amidst lush greenery. Warm light emanates from the large windows, highlighting the inviting entrance. A spacious driveway leads up to the house, surrounded by tall trees reflecting the evening sky.