Holiday rentals with outdoor seating in Hilton Head Island

4.89 out of 5 average rating, 228 reviews

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March ‘26 and brand new,from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa - with all of the amenities needed to enjoy a relaxing stay at the Hilton Head Beach & Tennis resort. Our villa is located just steps from the only elevator in the building. Our resort offers the largest pool on the island, several restaurants, a large playground & picnic area, on site bike rental, 24 hour gated security, 8 lighted tennis courts, and 6 pickleball courts.

4.84 out of 5 average rating, 264 reviews

A spacious screened porch equipped with a dining table and chairs offers a relaxing area for gatherings. Two ceiling fans provide comfort, and a fireplace adds a cozy touch. A large window showcases the private backyard, enhancing the connection to the outdoors.

Home in Shipyard

Private Beach Access-Pet Friendly-Hot Tub!

Welcome to The Beach House-A Family Fun Home! Immerse yourself in the ambiance of your 4-bdrm oasis, featuring a separate Bunk House for added privacy. Luxuriate in your hot tub under the stars in the HUGE backyard with Fire Pit and Covered Grill pole barn. Challenge your friends and family to ping pong or unwind in the screen porch with fireplace and dining area. With a Gorilla Cart at your disposal, hauling beach gear is a breeze. Get ready for endless fun and memories at your beach getaway!

A spacious studio apartment is shown, featuring a king size bed draped in a patterned quilt. A dresser and lamp are positioned nearby, while a modern kitchen area is visible in the background. Natural light fills the room, highlighting the warm wooden flooring.

4.99 out of 5 average rating, 218 reviews

Sunset on the May / Historic Old Town Bluffton

Spacious studio apartment sits above a detached garage with your own private entrance located in the heart of Old Town Bluffton. A short stroll to nearby restaurants, boutiques and unbelievable sunsets on May River. New king size bed, appliances and large sectional couch. Full kitchen with plenty of space to relax and store your things. Nice size bathroom, full shower and an abundance of amenities like private fire pit, outdoor grill and patio table for your enjoyment. HH Beaches minutes away!

4.99 out of 5 average rating, 462 reviews

Guest House on Lawrence Street

UPDATED LUXURY, FASTIDIOUS CLEANLINESS in historic OldTown Bluffton’s coziest carriage house. OldTown’s vibe is just plain fun. Stoll 2 blocks to super restaurants, night life, art galleries, boutiques, antebellum homes & lush waterfront parks on the idyllic May River. New in 2018 w/ quartz counters, private bedroom w/ plush king-size bed, upscale bath w/ soaking tub, bright living/dining room, full kitchen & romantic rocking-chair porch up in moss-draped oaks. Read our Reviews—guests love it!

A renovated kitchen features modern stainless steel appliances including a microwave, oven, and dishwasher. White cabinetry and granite countertops create a clean aesthetic. Ample storage is provided by drawers and cabinets, while laminate flooring adds a warm touch to the space.

4.99 out of 5 average rating, 221 reviews

Few mins walk to beach 1st flr pools hot tub pball

Ready for a beach vacation with a side of golf, pickleball and biking? Welcome to our newly renovated 1st floor villa in Fiddler's Cove. STR Permit# 24587. Our villa is a 6-7 minute walk to Folly Field beach with private beach access. THE best sunrises, just a few minutes away. Surrounded by world class golf courses and fantastic restaurants. Onsite amenities include 2 pools, a hot tub, racquetball, pickleball, tennis and gym. Pools open from March 1 - October 31 and hot tub open year round.

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, 104 reviews

Governor’s Quarters Pet Friendly, Fenced in Yard

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 mins from the SeaPines Beach Club and HarbourTown Golf Links and the heated community pool! Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, HarbourTown Lighthouse, & most importantly- the beach!

An aerial view captures the villa and surrounding area, highlighting the proximity to the beach. The ocean is visible in the background, while the spacious grounds feature multiple buildings and a parking area. Nearby greenery enhances the coastal atmosphere.

4.88 out of 5 average rating, 163 reviews

Ocean View 1-bdrm. Steps to the Beach. Sleeps 6.

Enjoy the Ocean views from the balcony of this newly remodeled 1-bedroom condo. Comfortable furnishing throughout. Perfect for a couple or family. The condo sleeps 6 with a queen bed in the private bedroom, sleeper sofa, and galley style bunks in the hallway. The kitchen is fully stocked. Enjoy dining outside as you enjoy the ocean view from the 2nd. floor balcony. The bathroom with tub/shower can be accessed from the bedroom or hallway. Beach chairs, umbrella, and cooler are provided.

4.92 out of 5 average rating, 115 reviews

BEACH PATH At Hilton Head Beach and Tennis Resort

🏖🏖🏖 Book your Summer trip with us!!!! Experience the ultimate beach getaway at our charming villa located within the gated Hilton Head Beach and Tennis. This oceanfront property boasts the largest oceanfront pool on the island, beach volley ball , tennis courts, pickle ball, bike rentals, a playground, grill/picnic area and three delightful restaurants. Nestled-mid island, our villa is conventiently located two miles from Shelter Cove/Palmetto Dunes. Trolley pickup onsite.

Villa in Hilton Head Island

The outdoor space features a year-round heated pool surrounded by lush greenery, with a clear view of the ocean. Umbrellas offer shade over picnic tables, while tall trees enhance the serene atmosphere of the beachside setting.

4.97 out of 5 average rating, 123 reviews

Oceanfront Scandi Oasis Amazing View & Heated Pool

Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

4.89 out of 5 average rating, 174 reviews

Available 6/7! King Bed/pools/3 blocks to beach

Stay just minutes from the beach and Coligny Plaza in this cozy, first-floor condo. Enjoy a renovated bathroom, a full kitchen with washer and dryer, and a Keurig for your morning coffee. The community has both an indoor and outdoor pools - updated in 2025. Our unit is the perfect home base to explore everything Hilton Head Island has to offer. This is the A unit of a lockout condo; the B unit may be occupied during your stay, but both are private and separately accessed.

4.95 out of 5 average rating, 137 reviews

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!

5 out of 5 average rating, 117 reviews

Condo in Sea Pines

5 Star Location-Harbourtown-Walkable Area

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Popular amenities for Hilton Head Island outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

Home in Hilton Head Island

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, 112 reviews

6 BR, Sleeps 26, Beach Time

Home in Hilton Head Island

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, 117 reviews

98 Sandcastle Ct

Superhost

5 out of 5 average rating, 3 reviews

51 Night Heron - Sea Pines, Dogs Welcome, EV Charg

A charming circular home is nestled among tall trees, featuring a spacious deck with white lounge chairs. The wooden steps lead up to the entrance, showcasing large windows that allow ample natural light. The surrounding greenery enhances the sense of privacy and seclusion.

4.98 out of 5 average rating, 91 reviews

Harbour Town Tree House | Deer Island | HT Pool

4.95 out of 5 average rating, 130 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

4.89 out of 5 average rating, 18 reviews

Private Pool ~ Cabana ~ 5 Deer Run Lane

Home in Hilton Head Island

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, 37 reviews

Steps to the Beach - Perfect All-Season Getaway

4.85 out of 5 average rating, 115 reviews

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.

Home in Palmetto Dunes

Palmetto Dunes House: Private Pool, PDBeach, Golf

Apartment rentals with outdoor seating

An inviting living space is seen, featuring a light gray sofa and a coffee table, with soft lighting from the lamps. A dining table is positioned nearby, complemented by two modern bar stools at a counter. The kitchen area is visible in the background.

4.84 out of 5 average rating, 187 reviews

Best of Bluffton

A living area features a comfortable sofa and stylish coffee table placed on a patterned rug. Natural light filters through the large window, illuminating the decor. A kitchenette with modern appliances is visible, along with sliding glass doors leading to an outdoor deck.

4.99 out of 5 average rating, 169 reviews

Charming carriage house in Bluffton

A balcony table is set with two clear wine glasses and a single pink rose in a vase. Green foliage and palm trees frame a view of the ocean and beachfront, creating a serene atmosphere against a clear blue sky.

4.85 out of 5 average rating, 247 reviews

Priceless Ocean View, King Bed, Heated Pool

4.95 out of 5 average rating, 37 reviews

Apartment in Sea Pines

Sea Pines Villa – Walk to Beach, Pool, & Salty Dog

Large windows frame stunning ocean views, allowing natural light to flood the room. A flat-screen TV is positioned on a glass stand opposite the windows, with a white shelving unit displaying decorative items. The space features maple hardwood flooring and a sliding glass door leading to an outdoor area.

4.83 out of 5 average rating, 192 reviews

Jim's Stunning Direct Ocean Front 2BR Villa

Superhost

A wooden boardwalk extends across sandy terrain, leading towards a serene coastal view. Lush green grass is visible on both sides, with a calm ocean horizon meeting a partly cloudy sky above.

4.83 out of 5 average rating, 135 reviews

Quiet Life by the Beach

A cozy living space is depicted with a blue sectional sofa adorned by decorative pillows. A dining table is set with plates and wine glasses, while large sliding doors provide access to a private balcony, allowing natural light to fill the room.

4.91 out of 5 average rating, 98 reviews

1BR/1BA-HHBT/Direct Beach Access

4.88 out of 5 average rating, 8 reviews

Steps to the Surf! Top-Floor w/Stunning Ocean View

Condo rentals with outdoor seating

An open living area features plush seating, including a blue chair, a light sofa, and a coffee table. Natural light filters through sliding glass doors that lead to a patio. A wall-mounted flat-screen TV is visible, and a dining area with a round table is nearby.

4.96 out of 5 average rating, 142 reviews

Island Song 2:Updated; 2B/2B; 7 min walk to Beach!

A vibrant sunrise is captured over the Atlantic Ocean, illuminating the horizon with warm hues of orange and yellow. The sun's rays radiate across the calm water, casting reflections on the sandy beach below.

4.96 out of 5 average rating, 216 reviews

Ocean Overlook - The Ultimate Vacation Experience

A wooden boardwalk leads through grassy dunes towards the beach. The path extends toward the calm ocean, under a gray sky. Soft sand is visible at the boardwalk's end, inviting guests to access the beachfront.

4.96 out of 5 average rating, 355 reviews

Ocean View & Steps to Beach! Remodeled HHBT Condo

4.98 out of 5 average rating, 142 reviews

A living area is characterized by a comfortable seating arrangement, featuring a light-colored sofa and a patterned armchair. A wooden coffee table is placed centrally, and a television is mounted above a decorative fireplace. Large windows provide views of the outdoor deck and surrounding greenery.

Condo in Shipyard

1BR/2BA condo w/private beach access in Shipyard

A sunlit living space features a navy blue sofa and an elegant dining table surrounded by four chairs. Large sliding glass doors provide access to the oceanfront balcony, where views of the beach and coastal landscape can be seen in the distance.

4.97 out of 5 average rating, 223 reviews

Oceanfront Luxury! KING BED Beach Bar & Pickleball

A modern kitchen area is showcased with stainless steel appliances and white cabinetry, complemented by a light wooden countertop. A cozy seating area is indicated by a curved sofa, while a large television sits on a wooden stand, enhancing the welcoming ambiance.

4.89 out of 5 average rating, 227 reviews

Top Floor- Ocean Views- Coastal Living

4.9 out of 5 average rating, 268 reviews

A calm bedroom features a spacious bed with a pink patterned quilt, complemented by a decorative beach-themed sign above. Two white closet doors are visible along one wall, while a bedside table holds a lamp. Coastal decor accents enhance the serene atmosphere.

Condo in Palmetto Dunes

HHI. Easy Direct Beach Access. 3 pools- 1 indoor.

The living area features a spacious sectional sofa arranged around a small coffee table. Natural light enters through the sliding doors, leading to an outdoor balcony. A decorative wall piece adds visual interest above the sofa, while a lamp and potted plant contribute to the inviting setup.