Holiday rentals with outdoor seating in Pinehurst

4.98 out of 5 average rating, 162 reviews

The exterior of a rustic cottage is framed by a large tree, with a well-kept lawn and flower beds. A paved pathway leads to the front porch, where seating is arranged under the shelter of the roof, inviting guests to enjoy the outdoors.

Cottage in West End

Juniper Pines Cottage

A very nice place to stay! Nestled in a peaceful, yet convenient area near Pinehurst "home of golf", North Carolina, our cottage invites the traveler to a pleasantly rustic setting. Built in 1943, our lovely cabin is completely renovated and filled with country charm. ATTENTION!!! PLEASE READ THIS & HOUSE RULES BEFORE SENDING INQUIRY. *PROFILE VERIFICATION MUST INCLUDE GOVERNMENT ID (ie, state issued license) *FOR THE HEALTH & SAFETY OF ALL GUESTS, WE MAINTAIN A NO PETS, NO EXCEPTIONS POLICY.

Cottage in Southern Pines

The entrance to a charming cottage is framed by lush greenery and well-maintained landscaping. A stone pathway leads to the front door, while a gravel driveway guides visitors through vibrant shrubs and trees.

4.96 out of 5 average rating, 384 reviews

The Ace Cottage - Tiny-home Feel, Close to golf

Unwind in the privacy of this adorable tiny-home! Just over a mile from downtown Southern Pines and less than 15 min to the famous Pinehurst Resort. Features a King size Nectar bed, Fire TV, WiFi, shower with tankless water heater a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge w/ freezer, toaster oven, and electric skillet), beautiful stone patio, professional landscaping, pet yard access, brand new floors, and a large driveway. The perfect spot for a quiet night!

The living area features a comfortable gray couch with orange and gray accent pillows, paired with an accent chair in a geometric pattern. A rectangular coffee table sits on a soft area rug, illuminated by soft lamp light and natural light from the window.

4.99 out of 5 average rating, 137 reviews

Long Drive On No. 5 - 1BR Condo, GREAT Golf Views

Renovated, centrally located condo in Pinehurst - only a 10 minute walk to the Pinehurst Golf Clubhouse! "Long Drive On No. 5" is a newly renovated, second-story one-bedroom condo perfectly located on hole #16 of Pinehurst No. 5 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy & luxurious finishes combined with an excellent location make this condo perfect for a weekend golf getaway or an extended stay!

4.94 out of 5 average rating, 135 reviews

A dining area features a wooden table surrounded by four chairs, set against a white brick wall with decorative letters spelling 'EAT.' Built-in cabinetry and a small wine cooler are present, contributing to the open and bright space illuminated by natural light from the window.

Villa in Pinehurst

A Cozy Retreat on No. 5

Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.

Farm stay in Southern Pines

The exterior of the cozy barn cottage features a brick facade and white paneling, complemented by a shaded porch with seating. Two stable doors are visible, surrounded by lush greenery and tall trees, creating a serene country atmosphere.

4.99 out of 5 average rating, 193 reviews

Finally Home Farm Bed and Barn

Bring your horse and your golf clubs! Welcome to Finally Home Farm Bed and Barn! A private 1 bedroom barn converted into a quaint cottage. Located on a peaceful farm just 2 miles from downtown Southern Pines, 1 mile from the back gate of Ft. Bragg and next to Weymouth Woods State Park, Finally Home Farm is the perfect place to explore all the Sandhills has to offer. *We are horse ($40) and dog friendly ($50) pet fee with Pre-Approval. Please include this info in your pre-booking.

Guest suite in Downtown Southern Pines

A quaint exterior of a bungalow is shown, framed by tall trees and lush greenery. A trellis is visible, adding charm to the entrance. Natural light filters through the scene, creating a warm ambiance in the garden area.

4.92 out of 5 average rating, 500 reviews

Cozy Studio in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this charming small, yet quaint & cozy self contained studio/efficiency which is attached to a 1930's bungalow. Just steps to our idyllic downtown. (Literally 1 block). Guests will have the entire studio for their private use. (bed, bath, kitchenette) Central heating and air with thermostat 1 bed / 1 bath. Private entrance. Street parking. 'Strict' No Smoking Policy

4.94 out of 5 average rating, 140 reviews

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

**Pool CLOSED for the season** Welcome to Lakeview Landing, located in the heart of Pinehurst golf! With a second story view of Lake Pinehurst, guests can relax on the balcony or enjoy the community pool! This quiet neighborhood shares close proximity to several great golf courses and has easy access to the BEST parts of Pinehurst: historic downtown, Fair Barn + Harness Track, Pinehurst Resort + Clubhouse, etc. Plus, it's a quick drive to nearby Southern Pines + Aberdeen!

Guest house in Southern Pines

The Tudor Revival Carriage House is set amongst tall Longleaf Pines, with warm lighting emanating from its windows. The structure features a gravel driveway, dual garage doors, and is complemented by lush greenery around its perimeter.

4.98 out of 5 average rating, 259 reviews

Historic Southern Pines Carriage House

Just minutes from Pinehurst and only one mile from downtown Southern Pines, this Tudor Revival Carriage House keeps you close to golf and activities! Enjoy a peaceful setting surrounded by an acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Enjoy area golf courses or stop in when visiting Penick Village, the Carolina Horse Park or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO PARTIES.

A spacious living area features a gray sectional sofa with colorful cushions, complemented by a wooden coffee table. Floor-to-ceiling windows admit natural light, while the wood flooring adds warmth to the room. A dining area is visible in the background.

4.98 out of 5 average rating, 827 reviews

The Knotty But Nice Treehouse of Pinehurst

Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.

A comfortable sitting area includes a gray sectional sofa paired with a round coffee table, adorned with small decorative items. Natural light enters through patio doors leading to a private garden. A queen bed with a light coverlet is positioned nearby, enhancing the cozy ambience.

4.98 out of 5 average rating, 300 reviews

Pinehurst #6 Garden Getaway

A warm welcome to our cozy 1 BR/1 BA apartment in the Pinehurst #6 community. It has a queen bed and a queen sofa bed if needed. We are close to the Village of Pinehurst and dozens of amazing Golf courses. We are less than 2 miles from First Health Moore Regional Hospital. Nearby you can enjoy shopping, dining, 4 local breweries and a winery. We also offer housekeeping for only $ 10 a day. PLEASE LET ME KNOW, when booking IF YOU NEED THE SECOND BED.

An open living area showcases a pair of brown leather sofas facing a wall-mounted television. A wooden dining table with four chairs occupies one corner, while large windows with sheer curtains offer a view of the outside. A patterned area rug sits beneath the seating arrangement.

4.94 out of 5 average rating, 170 reviews

Fairway Condo

This updated condo is located on the 17th hole fairway of the Pinehurst No. 5 Golf Course. It is perfect for golfers as well as travelers visiting Pinehurst area. It is minutes away by car to the Pinehurst Clubhouse and local restaurants. It features a 55 inch smart television in the living room, and a television and two double beds in each bedroom. It also features a custom built golf bag rack to keep your equipment safe and secure during the night.

A spacious studio is illuminated by natural light, featuring two large beds with plush bedding. A comfortable seating area is positioned near a window, with views of the lush outdoors. Modern furnishings and a breakfast bar complement the inviting layout of the space.

4.98 out of 5 average rating, 133 reviews

The Lucky Lie - Entire Condo in Pinehurst

Come relax at the luxurious Lucky Lie! This beautifully renovated studio condo is located just off the beaten path on Pinehurst No. 3, but still perfectly situated for an easy approach into downtown Pinehurst and the surrounding Sandhills. Unwind after your rounds on the porch over looking No. 3, 16th fairway, relax in front of the electric fireplace, or knock out some work in the dedicated workspace, the Lucky Lie has what you're looking for!

Popular amenities for outdoor seating rentals in Pinehurst

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.93 out of 5 average rating, 69 reviews

A modern kitchen and dining area feature sleek dark cabinetry and stainless steel appliances. A wooden table with bench seating is positioned nearby. A decorative clock and a vase with flowers add a touch of warmth to the space illuminated by natural light.

Home in Southern Pines

New Pines Retreat

A spacious outdoor area features a game table set with large red, white, and blue Connect Four and Jenga-style games. The background showcases a wooden fence and tall trees, providing a natural setting for leisurely entertainment.

4.99 out of 5 average rating, 109 reviews

Perfect golf getaway - quick drive to all courses

A unique tree house is set among tall pine trees, featuring a wraparound deck and steps leading to the entrance. The structure is elevated, with large windows allowing natural light inside. The exterior displays flags representing the United States and Maryland.

4.92 out of 5 average rating, 73 reviews

Chesapeake Tree House - golf front retreat

The exterior of the home displays a welcoming single-story structure set on a spacious lawn. A paved driveway leads to a two-car garage. A covered front porch, adorned with hanging plants, provides a shaded entryway, surrounded by lush greenery and blooming flowers.

5 out of 5 average rating, 94 reviews

Cheerful Eclectic Pinehurst home

Home in Downtown Southern Pines

A cozy living room features a leather sofa complemented by colorful cushions. A wooden coffee table is set on a light area rug, with decorative items arranged on top. Dark green walls provide a backdrop for wall art and plants, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 107 reviews

The Gallery - 2 bd Boutique Southern Pines Cottage

A charming historic home is framed by lush greenery and features a front porch with a rocking chair. The exterior is painted in soft yellow with dark shutters. An American flag hangs beside the door, enhancing the inviting entrance.

5 out of 5 average rating, 117 reviews

Historic 5 bedroom cottage walk to village & golf!

5 out of 5 average rating, 29 reviews

A single-story home is framed by lush greenery and tall pine trees, creating a peaceful ambiance. The front yard features well-maintained grass and colorful shrubbery. A covered porch with seating is visible, inviting guests to relax outdoors.

Home in Southern Pines

The Cottage on Midland

Home in Downtown Southern Pines

A cozy living area features a gray sofa and a light accent chair, complemented by a rustic wooden coffee table. Natural light pours in through two windows, and soft area rugs add texture to the floor. An artwork depicting a horse adds a charming touch.

4.95 out of 5 average rating, 111 reviews

Bourbon On Bennett, Bespoke Townhome in DTSP

Apartment rentals with outdoor seating

4.96 out of 5 average rating, 198 reviews

A cozy living area is presented, featuring two tan accent chairs and a dark sofa. A wood coffee table is centered on a patterned rug. The kitchen area includes a bar with two brown stools, equipped with modern appliances and tasteful decor.

Flat in Southern Pines

Tanglewood Farm Horse Farm- The Fox Den Apartment

A comfortable living area showcases a light gray sofa adorned with blue pillows, accompanied by a black chair. A decorative coffee table sits on a patterned area rug. Natural light floods the space through large windows, highlighting a cozy electric fireplace and contemporary artwork on the wall.

5 out of 5 average rating, 84 reviews

Captain’s Choice

A spacious living area features a gray sofa, accent chairs, and a glass coffee table. Large sliding doors provide natural light and scenic views of the outdoors. A dining table is set with blue placemats and white napkins, enhancing the inviting atmosphere.

5 out of 5 average rating, 10 reviews

The Pinehurst Perch

A welcoming entrance features a pathway leading to a covered porch. The pathway is bordered by natural stone landscaping, complemented by lush green plants and shrubs on either side. The exterior of the home showcases a light-colored siding and decorative shutters.

Flat in Southern Pines

Charming Basement Apartment

A welcoming living area features a light-colored sofa and two patterned armchairs arranged around a wooden coffee table. A neutral area rug covers the hardwood floor, and a fireplace provides a focal point. Natural light enters through a window with soft drapes.

4.8 out of 5 average rating, 5 reviews

Great Golf Getaway - Pinehurst

Superhost

An arched brick gate in a purple hue opens into a private courtyard, lined with wooden fencing and greenery. Paved brick pathways meander through the garden, featuring a variety of plants and neatly arranged flower beds, creating an inviting outdoor space.

Flat in Downtown Southern Pines

4.78 out of 5 average rating, 40 reviews

Slice of Seclusion in Downtown Southern Pines

4.97 out of 5 average rating, 97 reviews

A well-appointed studio features a queen bed with a white blanket, a dark blue sofa, and a stylish rug in varied colors. A small table with two chairs and a potted plant enhance the space. Natural light fills the room through a large window adorned with dark curtains.

Flat in Southern Pines

Private&Comfortable Studio for 2 in Southern Pines

A remodeled bathroom features a marble countertop with a pink vanity and organized storage drawers. Soft lighting enhances the space, which connects to a cozy sleeping area seen through an open door. Elegant wall decor and a rug complement the soothing atmosphere.

5 out of 5 average rating, 15 reviews

Pied-à-Terre Pinehurst

Apartment rentals with outdoor seating

A welcoming living space features a comfortable sofa, two armchairs, and a coffee table set on a patterned rug. Natural light fills the room through sliding glass doors, which offer a view of the outdoor deck with additional seating and green surroundings.

4.9 out of 5 average rating, 93 reviews

Golf-front gem in beautiful Pinehurst, NC!

A spacious living area is presented with a large, dark sectional couch complemented by assorted cushions. A circular wooden coffee table is positioned in front, and natural light enters through expansive glass doors that offer views of the outdoor space. A small area rug and bookshelf enhance the comfort.

5 out of 5 average rating, 28 reviews

Pinehurst Playground on the Lake

An aerial view captures the Greenside Getaway's proximity to Pinehurst's golf courses. Surrounding trees provide a lush backdrop, while visible golf paths indicate convenient access. The layout highlights the condo's location relative to nearby amenities, enhancing the overall sense of accessibility and leisure.

4.98 out of 5 average rating, 110 reviews

Greenside Getaway️! Walk to Clubhouse and Cradle!

A cozy living area is presented with a blend of soft gray sofas and armchairs arranged around a wooden coffee table. A decorative rug lies beneath, complemented by a wall clock and tasteful wall art. Natural light enhances the welcoming atmosphere.

5 out of 5 average rating, 136 reviews

New updated 2BD,2BA, Condo! Free Pool, WIFI etc.

A bright living room features a cream-colored sofa with decorative pillows, accompanied by a green accent chair. A glass coffee table is centrally placed on a light rug, and a television is mounted on a stand. Natural light enters through large windows with sheer drapes.

4.91 out of 5 average rating, 88 reviews

Charming Pinehurst Golf Front Condo

Apartment in Whispering Pines

A cozy living room features a comfortable sectional sofa adorned with decorative pillows. A tufted ottoman sits at the center of a colorful area rug. A bookshelf filled with various games and DVDs is complemented by a TV on a media console, with two wooden chairs positioned nearby.

4.94 out of 5 average rating, 34 reviews

Welcome to Backyard Retreat!

4.95 out of 5 average rating, 259 reviews

* Top Rated - Guest Fave - Golf Front Condo *

A comfortable living area is presented with a green sofa adorned with colorful throw pillows and a cozy knit blanket. A coffee table sits centrally on a patterned rug, complemented by a chair featuring a teal throw. Natural light filters through large windows, enhancing the space.