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 Summer Vacation

(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.

5 out of 5 average rating, 9 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 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, 134 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.

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.

4.94 out of 5 average rating, 121 reviews

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.

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.

4.99 out of 5 average rating, 232 reviews

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 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.

4.95 out of 5 average rating, 125 reviews

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 is a 5-10 min ride by bike and a 15 min walk. Beach towels/umbrellas/chairs not provided. Pool/spa not heated.

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.

4.84 out of 5 average rating, 140 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Beautiful home located in Palmetto Dunes Resort. Deck with pool overlooking the first tee of Fazio Golf course with fantastic views of the sunset. Carolina room makes a great 5th bedroom. Private Cul-De-Sac street. Short walk to the beach, general store and tennis center. Enjoy all the amenities of the resort including its beaches, three golf courses, fishing, kayaking, tennis, pickleball, bike trails, restaurants and Dunes Buggy shuttle. Perfect for family beach trips or golf getaways.

4.75 out of 5 average rating, 4 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.

The image showcases a collage highlighting different areas of the Hilton Haven property. The top left features a wall mural of Hilton Head Island with a comfortable seating area. The top right displays a game room with a pool table. The bottom left shows the golf simulator setup with a putting green, while the bottom right exhibits the outdoor dining space and putting green in the backyard.

5 out of 5 average rating, 68 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.

A two-story house features a light blue exterior with white trim and black shutters, showcasing a spacious driveway. A six-person black golf cart is parked in front, contrasting against the landscaped area with tropical plants and a nearby streetlamp.

4.93 out of 5 average rating, 216 reviews

Enjoy time with family and friends

Home sleeps up to 22 guests (17 Beds) depending on sleeping arrangements and is in a Gated Community, Short walk to the Beach . Home has 5 Bedrooms plus bonus room with Bunk Beds, 4 Baths.. Open concept.. There is a deck of the living room with table and chairs also to enjoy. The heated screened pool and BBQ are for your enjoyment. Rear yard is fenced. 6 person golf cart available for rental at discounted rates. Dill Dinkers indoor pickleball close by.

4.93 out of 5 average rating, 15 reviews

FREE Pool Heat - Luxury Home - Pet Friendly

Escape to Hideaway, a cozy 2BR/2BA retreat in Sea Pines! Sleeps 6 guests with a private heated plunge pool (heated to 86°F in spring & fall), stylish interiors, & pet-friendly amenities. Relax in the open-concept living space, enjoy the outdoor patio with a grill & loungers, & explore Hilton Head’s beaches just 0.7 miles away. A perfect blend of privacy & coastal charm! 7 Pender Lane

Popular amenities for Hilton Head Island house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of the home is showcased at dusk, featuring a spacious heated pool illuminated in blue. Surrounding the pool are multiple lounge chairs, providing a serene outdoor space for relaxation. The multi-level structure is elegantly designed, with expansive balconies above and a well-lit entrance.

4.96 out of 5 average rating, 96 reviews

5 Bedroom-Beach Access-Pool-Sleeps 14!

An inviting outdoor area features a pool with a waterfall and fire features, framed by a spacious screened-in enclosure. Comfortable seating is arranged beside the pool, providing a scenic view of greenery and natural light filtering through the structure.

5 out of 5 average rating, 18 reviews

17 Firethorn - HGTV "Wow-Worthy", Pool, Fire Pit

An aerial view captures a charming home with a green roof, surrounded by lush trees. A rectangular pool is framed by a stone patio and lined with lounge chairs. A dining area can be seen on the deck, inviting outdoor meals in a serene environment.

4.67 out of 5 average rating, 39 reviews

Hilton Lagoon by AvantStay | Designer Home + Pool

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.

4.86 out of 5 average rating, 22 reviews

Coastal Bliss

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 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, 123 reviews

Encanto of the Lowcountry in Old Town Bluffton

Aerial view of a private backyard featuring a kidney-shaped pool surrounded by a natural stone patio. Comfortable lounge chairs are positioned by the pool, and a covered area with overhead beams houses an outdoor kitchen. A fenced perimeter ensures privacy.

5 out of 5 average rating, 40 reviews

54 Folly Field Rd - Amazing Beach Home with Pool

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

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 serene pool area is featured, surrounded by lush greenery and tall trees. Loungers are arranged neatly around the pool, inviting relaxation. The buildings in the background exude a charming design, with balconies overlooking the pool, enhancing the spacious setting.

5 out of 5 average rating, 5 reviews

2bd 2b Ocean Palms Inc. daily golf & Westin access

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

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!

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, 77 reviews

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, 18 reviews

Oceanfront condo with elevator and gated entrance!

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

Private house rentals

A well-lit bedroom features two spacious beds, each adorned with vibrant blue and green bedding. A decorative wall basket adds a natural touch, while a window with patterned curtains allows for natural light. A small chair and side table enhance the room's functionality.

4.99 out of 5 average rating, 95 reviews

6 BR, Sleeps 26, Beach Time

The exterior of the home features a grand two-story structure with a large covered porch and multiple entry points. Lush landscaping with palm trees enhances the inviting curb appeal. A paved driveway provides access to the garage, surrounded by neatly trimmed bushes and grass.

5 out of 5 average rating, 32 reviews

5 Sandy Beach Trail- Beach House w/ Private Pool

The exterior of the two-story villa showcases a modern design with a light-colored façade and multiple windows. A welcoming entrance is framed by manicured shrubs and greenery, creating an inviting approach. A short pathway leads to the main door, highlighting the tranquil surroundings.

4.96 out of 5 average rating, 27 reviews

Ocean Gate Hideaway! 7 min walk to the beach

5 out of 5 average rating, 9 reviews

Short walk to Beach!

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

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, 78 reviews

Hilton Head Island Beach Cottage/House

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

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.