House holiday rentals in Hilton Head Island

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, 386 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King beds*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, 138 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 Dunes House is 5-10 min by bike or 15 min walk. Beach towels/umbrella/chairs not provided. Pool/spa heat unavailable after 6/1/26

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, 106 reviews

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

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, 123 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 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

Located less than a mile inside the Sea Pines front gate this updated Carolina Place home has lagoon views framed by high ceilings and South Carolina live oaks. This scene can be enjoyed on the elevated back deck complete with comfortable outdoor seating, and a full size grill. Inside there is plenty of room for the whole family with 3 bdr and a sleep-in den area. This home offers a semi-open, fully-stocked kitchen, indoor and outdoor dining, board games, high speed internet, and cable TV.

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, 147 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.

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, 122 reviews

Cozy beach house w/Private Heated Pool near park

Short walk to Singleton beach or Burkes beach. This oversized 4 bedroom 4 ensuite is the perfect retreat close to everything the Island has to offer. The home features a screened in pool with TV and adjacent ping pong table. The open concept living space is perfect for entertaining with access to a large porch and grill. The property is steps away from Chaplin Park that hosts Tennis, Playground, Soccer, Baseball, Basketball, Trails and Fields for the kids to play. Sleeps 12.

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, 102 reviews

6 BR, Sleeps 26, Beach Time

Just a short walk down Folly Field to the beach & locally managed by the Owner. This brand new beach house has 6 bedrooms and 4 full bathrooms. Linens, Bath Towel sets & Pool Towels included. An Amazing bunk room/play room with 6 full size bunk beds, high end furnishings, fully equipped kitchen, dining for the entire crew, 2 huge balconies with lovely lagoon views, large outdoor living area with television and shaded pool. We have thought of everything & we are at your service!

5 out of 5 average rating, 77 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.

4.93 out of 5 average rating, 30 reviews

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.

Home in Shipyard

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

Gourmet Coffee Lovers Paradise. And, over 1000 *5* star reviews! You found the perfect vacation home where you can enjoy a private pool with a spacious layout. Comfortably sleep 8 in 4 private bedrooms. The kitchen is fully equipped with everything needed to prepare a gourmet meal. You can enjoy dining in the large formal dining room, the sunroom adjacent to the kitchen, or outside. *The pool and spa can be heated for an additional fee.

Superhost

5 out of 5 average rating, 3 reviews

Free Daily Activities + Walk to Beach!

🏆 We're a Superhost located in Hilton Head Island with 700+ fantastic property reviews. Voted LowCountry's Best year after year, your group is sure to enjoy your next Hilton Head Island escape in this stunning property. 🏝️ 6-Minute Walk to Fish Haul Beach | 7-8 Minute Walk to Port Royal Sound ☀️ Beautiful View | Features a Tesla Charger ⛳️ Save even more when you book6 Hammock Breeze and receive $300 in complimentary daily activities!

Popular amenities for house rentals in Hilton Head Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.86 out of 5 average rating, 65 reviews

~Couples Paradise~Villa W/Pool~Beachfront Resort

Superhost

A bright living area features high ceilings and large windows with light filtering through blinds. A comfortable sectional and a wicker chair surround a central coffee table. Soft textures are evident in the area rug and throw pillows, creating a welcoming environment.

Home in Shipyard

4.86 out of 5 average rating, 7 reviews

Blue Heron Dunes

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.

4.93 out of 5 average rating, 54 reviews

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

5 out of 5 average rating, 9 reviews

The living room is designed with a large sectional couch and two blue accent chairs, with a neutral-toned area rug underneath. A flat-screen TV is mounted on the wall, and a mixture of shelves and decorations adds to the inviting space.

Home in Shipyard

Spacious 4Bd/3Ba Pet/Beach/Pool/Tennis/Pickleball

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, 104 reviews

Private pool/spa : pool heat available : Kg master

4.9 out of 5 average rating, 31 reviews

96 Forest Drive in Sea Pines

A colorful dining area features sturdy wooden tables and benches, set beneath a shaded canopy. Tropical palm trees and a sandy path leading to the beach can be seen in the background, providing a relaxed atmosphere for guests.

4.91 out of 5 average rating, 80 reviews

Apartment in Hilton head resort

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, 78 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, 30 reviews

Starfish Beach House with Pool and Bikes

A community pool area is surrounded by lush greenery, featuring a large swimming pool with a gentle slope and steps for easy access. Several lounge chairs are positioned around the pool, providing relaxation spots, while a shaded area with umbrellas is visible. Safety floats are present in the water.

5 out of 5 average rating, 28 reviews

Sea Pines Serenity!

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.

4.93 out of 5 average rating, 88 reviews

Hilton Head Island Beach Cottage/House

5 out of 5 average rating, 11 reviews

1 Baynard Park - Sea Pines, Lagoon Views, Elegant

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, 53 reviews

Sea Pines Villa - Walk to Beach, Golf and Tennis

5 out of 5 average rating, 19 reviews

Home in Bluffton

Casa Del Café, Walk to Old Town

A modern home is surrounded by lush greenery, featuring large glass windows that invite natural light. A spacious outdoor area includes multiple lounge chairs and umbrellas, along with a large dining table. A pool area is visible, enhancing the outdoor living experience.

5 out of 5 average rating, 11 reviews

Island Paradise Getaway

Private house rentals

A spacious beach house is presented with a bright exterior, featuring multiple balconies and staircases leading to the front entrance. The property is surrounded by palm trees and includes a fenced-in area with a private pool nestled in the front yard.

4.92 out of 5 average rating, 63 reviews

Luxury 7BR Beach House w/ Pool, Hot Tub &Game Room

4.97 out of 5 average rating, 29 reviews

Hilton Head Island Beach House - Sea Pines Resort

An outdoor area features a heated private pool surrounded by a spacious patio and lounge chairs. The home, with updated siding, has a shaded seating area and a barbecue grill. Lush greenery and colorful flowers enhance the tranquil ambiance.

4.84 out of 5 average rating, 109 reviews

Palmetto Dunes House: Private Pool, PDBeach, Golf

The exterior of the house presents a modern coastal design, featuring a spacious deck with multiple seating areas, a large umbrella, and a grassy surrounding. Large glass doors invite natural light into the interior while a BBQ grill is visible on the deck.

5 out of 5 average rating, 34 reviews

RBC Heritage Right In Your Backyard

5 out of 5 average rating, 19 reviews

Sea Pines Home w Large Deck | Great for Couples!

A bright living area features a light-colored sofa and a comfortable blue accent chair. A coffee table with a tufted top stands in the center. Large glass doors lead to an outdoor deck, allowing natural light to fill the space.

5 out of 5 average rating, 147 reviews

Walk to Harbour Town: Airy Treehouse w/ Bikes

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.

4.84 out of 5 average rating, 168 reviews

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

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.