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.

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.

4.87 out of 5 average rating, 378 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

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 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 a 5-10 min ride by bike or 15 min walk. Beach towels/umbrellas/chairs not provided. Pool/spa heat for extra fee.

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.

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, 28 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 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, 163 reviews

Luxe Family Gem-Heated Pool~Walk to Beach~Elevator

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!

The open-concept living space features handmade Saltillo tiles and a vaulted ceiling. A comfortable couch and a fireplace are visible along with a large dining table. A staircase leads to the upper level, enhancing the spacious layout. Sliding glass doors provide access to the outdoor area.

4.98 out of 5 average rating, 94 reviews

Governor’s Quarters: Stately Sea Pines Stay on HHI

Welcome to Governor's Quarters- your Luxury Hilton Head Getaway Stay Lowcountry in this stately-designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 minutes 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!

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

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.

5 out of 5 average rating, 3 reviews

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!

Popular amenities for Hilton Head Island house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 3 reviews

Beach Bungalow in Sea Pines’ Night Heron Community

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.

4.85 out of 5 average rating, 142 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

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

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 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, 25 reviews

Steps to the Beach - Perfect All-Season Getaway

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)

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

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, 29 reviews

Starfish Beach House with Pool and Bikes

A well-maintained outdoor pool area is surrounded by lush greenery and palm trees. Multiple lounge chairs with blue umbrellas are positioned around the pool. A wooden staircase leads down to the pool, creating an inviting pathway through the landscaped garden.

5 out of 5 average rating, 25 reviews

3 bd/3 bath Villa with daily golf & Westin access

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 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 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!

An airy living space is highlighted by soft white sofas and a large rug featuring ocean-themed designs. A ceiling fan hangs above, while natural light floods in through expansive glass doors. The room includes a cozy fireplace and a wooden coffee table in the center.

5 out of 5 average rating, 25 reviews

Sal and Babs Sea Pines Sanctuary

A serene screened porch is featured, showcasing two wicker chairs with blue and white striped cushions and a round dining table. Lush greenery surrounds the area, while soft natural light filters through the screens. A glimpse of outdoor seating can be seen in the background.

5 out of 5 average rating, 71 reviews

SeaPines,2 main suites/screen porch/6 bikes

Private house rentals

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, 9 reviews

Short walk to the 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 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

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, 51 reviews

Sea Pines Villa - Walk to Beach, Golf and Tennis

4.98 out of 5 average rating, 80 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

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.

5 out of 5 average rating, 17 reviews

Palmetto Dunes Renovated Villa

The spacious kitchen features a large quartzite island with seating for four. Modern stainless steel appliances are integrated into white cabinetry. A bowl of yellow flowers and citrus fruits adds a fresh touch to the elegant countertop, while natural light enhances the inviting atmosphere.