House holiday rentals in Hilton Head Island

4.99 out of 5 average rating, 390 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: Enjoy a Low Country Summer

(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.

4.99 out of 5 average rating, 136 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 serene backyard oasis is illuminated by soft lighting, showcasing a modern pool and hot tub. A pergola offers shaded seating, surrounded by lush landscaping and palm trees, creating a tranquil atmosphere perfect for relaxation and evening gatherings.

5 out of 5 average rating, 42 reviews

Luxury Beachside 6BR Coastal Paradise~Pool/Hot Tub

Step into paradise at this luxurious 6BR, 5BA beach house just 30 steps from Hilton Head’s quietest and most beautiful beach! Modern meets coastal charm in this beautifully renovated home, featuring a resort-style backyard with a pool, hot tub, and pergola with an outdoor TV. Sleeps 16 & dog friendly! Perfect for large families or groups. Enjoy unbeatable beach access and stylish comfort in the charming Folly Field neighborhood just minutes from world-class dining, golf, and island adventures.

4.94 out of 5 average rating, 122 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

Offered by owner /manager. Master bath w/ walk in shower, spacious bright open concept LR, DR, kitchen, w/ private cozy courtyard. Designer inspired coastal chic for the beachy atmosphere. Sit and relax in the courtyard, lounge in the sun while having an afternoon drink and BBQ. Watch golfers at the driving range or Trent golf course just a short walk from the villa. Go for a swim in 1 of 5 community pools. Under 10 minute walk to Palmetto Dunes beach or call seasonal dune buggy for a ride.

4.99 out of 5 average rating, 236 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!

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, 29 reviews

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

Welcome to The Heron Hideaway- your Luxury Hilton Head Getaway. Stay low country in this exclusively designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from SeaPines Beach Club and 6 mins from the Harbourtown Golf Links. Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, pool access, HarbourTown Lighthouse, & most importantly- the beach!

A modern two-story home is presented, featuring blue and white exteriors with large windows. A custom 6-seater golf cart is parked in the driveway, surrounded by manicured landscaping, including palm trees and shrubbery.

4.96 out of 5 average rating, 105 reviews

5 Bedroom Home w/ Private Pool & 6Seater Golf Cart

This professionally decorated 5 bedroom 4 bath single family home has a private heated pool, elevator, and custom 6 seater Alpha Club Car golf cart. This home is located on the north end of Hilton Head Island with a 5 minute walk or 2 minute golf cart ride to the less crowded Folly Field Beach area. 91 Sandcastle is the perfect vacation rental spot on Hilton Head Island because of its proximity to the beach, restaurants, golf courses and everything else this amazing island has to offer.

4.8 out of 5 average rating, 5 reviews

Walk to beach - 2BD/2BA retreat

Relaxing getaway for family and friends. Brigantine Quarters, located in Shipyard Plantation is one of the most picturesque properties on Hilton Head. With golf, shopping, dining, biking, and the beautiful beach nearby, BQ is your ideal vacation resort destination. 7 min walk to beach Pickleball/Tennis courts Grilling stations 2 outdoor pools 24 hr security guard Call Palmetto Bikes to reserve bikes in advance and your bikes will be in front of your condo when you arrive.

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

5 out of 5 average rating, 3 reviews

An expansive pool deck is illuminated with soft lighting, showcasing a private pool and built-in spa. A lounge area with multiple chairs is present, and a covered seating area is visible in the background. The setting sun casts warm hues over the space.

Home in Palmetto Dunes

47 Haul Away Estate @ Palmetto Dunes | Pool & Spa

Experience refined elegance at 47 Haul Away by Host & Home, a luxurious Palmetto Dunes estate with captivating golf course views. Unwind on the expansive pool deck with a private spa, outdoor bar, and grill, perfect for entertaining. Inside, enjoy a chef’s kitchen, a private office, and multiple sophisticated living spaces. Conveniently located near Hilton Head’s pristine beaches, world-class golf, and premier dining, this property offers the ultimate in Lowcountry luxury.

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, 47 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!

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.

Popular amenities for house rentals in Hilton Head Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 99 reviews

98 Sandcastle Ct

A contemporary three-story home is surrounded by lush landscaping, featuring a wide driveway leading to a two-car garage. Large windows provide ample natural light, while the front porch offers a welcoming entrance to the residence.

5 out of 5 average rating, 18 reviews

Luxury Beach Getaway/outdoor oasis-5 min. to beach

The outdoor area features a private pool surrounded by a sun-soaked patio. Comfortable lounge chairs are arranged on the pool deck, offering ample seating. The multi-level home showcases a spacious upper balcony with railings, enhancing the tranquil ambiance and inviting outdoor living space.

4.91 out of 5 average rating, 11 reviews

39 Oak Court: Sea Pines Luxury! 5 BR, 5.5 BA, Pool

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

4BR Shipyard Home w/ Private Pool + Beach Access

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, 46 reviews

Heels in the Sand- Private Pool & Putting Green

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

An aerial view captures a spacious backyard featuring a sparkling pool surrounded by lounge chairs. Lush green grass complements the area, while a putting green is visible to the right. The two-story house is prominently showcased, along with a garage and lush landscaping.

4.86 out of 5 average rating, 7 reviews

Coastal Oasis - 200 yards to Beach! (Both Units)

Weekly house rentals

5 out of 5 average rating, 3 reviews

Beach Bungalow in Sea Pines’ Night Heron Community

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, 29 reviews

Starfish Beach House with Pool and Bikes

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!

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.

4.8 out of 5 average rating, 25 reviews

Coastal Bliss

The entrance of the cottage features a light blue door surrounded by a wooden deck, framed by lush greenery and tall trees. A small sign reading 'Home' hangs next to the door, indicating a welcoming atmosphere.

4.81 out of 5 average rating, 27 reviews

17 Night Heron · Elegant, Stylish Beach Cottage

A bright living area is presented with a cozy arrangement of a spacious sofa and a gray loveseat. Natural light filters through window treatments, highlighting a round coffee table and decorative accessories. A console table with a mirror and a soft lamp complete the inviting space.

4.94 out of 5 average rating, 83 reviews

Hilton Head Island Beach Cottage/House

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.

4.91 out of 5 average rating, 22 reviews

Lagoon & Tidal Marsh Views w/Screened-In Porch

Private house rentals

A heated pool with a water slide is featured in the foreground, surrounded by lounge chairs positioned on a deck. The pool exhibits a distinctive shape, with clear blue water reflecting sunlight. Nearby, two multi-story houses are visible in the background.

4.96 out of 5 average rating, 23 reviews

The Beach House

A dining table is set with elegant dishes and glassware, creating a welcoming atmosphere. A bottle of wine sits in the center, surrounded by decorative accents. Soft natural light filters through large windows, enhancing the room's serene ambiance.

4.95 out of 5 average rating, 41 reviews

(22)Hot Tub, Pool &Tennis, Sauna, Patio

5 out of 5 average rating, 10 reviews

Short walk to Beach!

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 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!

4.98 out of 5 average rating, 81 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

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, 20 reviews

Oceanfront condo with elevator and gated entrance!

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.