Holiday rentals with outdoor seating in Pinehurst

4.98 out of 5 average rating, 163 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, 378 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!

A cozy living area is depicted, featuring a dark blue sofa facing a large television. Two light armchairs are positioned beside a wooden console, which holds books and decorative items. An intricate wall decoration and soft lighting create a calm ambiance.

4.95 out of 5 average rating, 253 reviews

* Top Rated - Guest Fave - Golf Front Condo *

Welcome to your perfect Pinehurst retreat! This clean, comfy ground-floor condo is ideal for golf trips, weekend getaways, or longer stays. Enjoy a well-stocked kitchen, cozy furnishings, and a screened porch with peaceful fairway views - a prime spot for morning coffee or evening wine. Super close to the Village, great dining and shops, the Fair Barn, harness track and Pinehurst Resort; just 10–15 minutes to Southern Pines and Aberdeen. Peaceful, walkable, and a consistent guest favorite!

4.96 out of 5 average rating, 126 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, 189 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, 486 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

A spacious living area features a deep sectional sofa and large dining table, surrounded by large sliding glass doors offering views of the outdoors. A 70" Smart TV is mounted on the wall, providing entertainment options for relaxed gatherings.

4.88 out of 5 average rating, 102 reviews

Comfortable Pinehurst Golf Condo - Walk to Resort

A perfect place to call home while exploring Pinehurst. Convenient location within a few minute walk to Pinehurst Resort Clubhouse and Cradle short course. A spacious 2 bedroom / 2 bathroom (4 beds) in quiet surroundings awaits to enjoy the tranquil beauty of Pinehurst. - Keyless Entry - On-site Parking - First Floor Unit - New Furnishings - Poker Table - Fully Equipped Kitchen - 2 Covered Patios - Golf Putting Mat - Hi-speed WiFi, 3 Smart TVs - Kid-friendly w/ pack n’ play

4.94 out of 5 average rating, 132 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!

4.98 out of 5 average rating, 815 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, 293 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, 162 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 bright studio condo features a king-size bed with a soft blue blanket and a mirrored circular light fixture above. Two comfortable armchairs and a desk with a chair are positioned near a sliding glass door that leads to a private deck with views of the golf course.

4.99 out of 5 average rating, 161 reviews

To The Green On #17 - Studio w/ GREAT Golf Views!

PERFECT LOCATION - only a 5 minute walk to the Pinehurst Golf Clubhouse! "To The Green On #17" is a second-story studio condo perfectly located on hole #17 of Pinehurst No. 3 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy yet luxurious finishes combined with an excellent location make this studio condo perfect for a weekend golf getaway or an extended stay!

Popular amenities for Pinehurst outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A warmly colored dining area is highlighted by a large round table surrounded by eight black leather chairs. Natural light enters through tall arched windows, complementing the rich orange walls and decorative white wainscoting. A classic chandelier hangs above, adding elegance.

4.99 out of 5 average rating, 144 reviews

The Ross Retreat - In Pinehurst

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, 104 reviews

Perfect golf getaway - quick drive to all courses

A view of a well-maintained golf course is captured, with a serene lake reflecting the sky. In the foreground, a flowering tree showcases delicate blossoms against a backdrop of tall pines, completing the peaceful landscape.

4.99 out of 5 average rating, 110 reviews

A Golf Front SFH 3 BR 2 BA in Pinehurst#6

An open living and dining area features high, vaulted ceilings supported by wooden beams. A brick fireplace is centered on the wall, accompanied by cozy seating arrangements on a plush area rug. A dining table is set with decorative accents, and large windows offer natural light.

4.97 out of 5 average rating, 75 reviews

Ivy Kirk Cottage in the Village of Pinehurst

A welcoming living space showcases games and relaxation with a poker table, stylish seating, and a vibrant mural of Pinehurst. Outside, Adirondack chairs face a scenic golf view, inviting guests to relax in the spacious backyard with modern amenities and comfortable furnishings.

4.96 out of 5 average rating, 106 reviews

The 19th hole | Sleeps 12 | 3 mins to Pinehurst

5 out of 5 average rating, 108 reviews

The exterior of a two-story cottage is shown, featuring a white clapboard façade with dark roofing. A covered porch is seen at the front, furnished with a small round table and four chairs, surrounded by landscaping with young plants and mulch.

Home in Southern Pines

New 5 Bedroom Cottage on Pine Needles Golf Course

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, 103 reviews

The Gallery - 2 bd Boutique Southern Pines Cottage

5 out of 5 average rating, 21 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

Apartment rentals with outdoor seating

5 out of 5 average rating, 58 reviews

A spacious outdoor pool is surrounded by a chain-link fence, with several lounge chairs arranged along its perimeter. Lush green grass and trees frame the area, while multiple buildings can be seen in the background, contributing to a serene environment.

Apartment in Carthage

Golf Getaway, 5 miles to Pinehurst

Apartment in Southern Pines

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.

4.96 out of 5 average rating, 196 reviews

Tanglewood Farm B&B Horse Farm- The Fox Den Suite

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, 80 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, 9 reviews

The Pinehurst Perch

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.

Apartment in Downtown Southern Pines

4.75 out of 5 average rating, 36 reviews

Slice of Seclusion in Downtown Southern Pines

A spacious living area is featured, furnished with a light-colored sofa and two decorative armchairs. Two lamps provide soft lighting, illuminating floral artwork on the wall. A wooden coffee table, adorned with magazines, is centered on a vibrant area rug. The kitchen is visible in the background.

Apartment in Whispering Pines

5 out of 5 average rating, 4 reviews

Lakefront Living in Whispering 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, 12 reviews

Pied-à-Terre Pinehurst

Condo rentals with outdoor seating

Superhost

The living area features a comfortable brown sofa and a blue-green accent chair, positioned on natural wood flooring. A coffee table sits in the center, with a decorative plant and a book. Large windows allow natural light, framed by light fabric curtains.

4.86 out of 5 average rating, 136 reviews

Cozy Golf-Front Condo 3 mins to PCC clubhouse

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.

4.91 out of 5 average rating, 92 reviews

Golf-front gem in beautiful Pinehurst, NC!

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, 107 reviews

Greenside Getaway️! Walk to Clubhouse and Cradle!

A unique treehouse structure is surrounded by lush greenery, featuring expansive glass windows that provide views of the landscape. A set of wooden stairs leads to the entrance, while manicured shrubs enhance the natural setting.

4.94 out of 5 average rating, 35 reviews

Treehouse Retreat on Pinehurst Golf Course

A living area features comfortable seating arrangements, including a gray sofa and an accent chair. Natural light filters in through large sliding glass doors, which open to a balcony. A flat-screen TV is positioned on a white entertainment unit, with a decorative tray and plants on the coffee table.

5 out of 5 average rating, 135 reviews

Clean & Updated2BD, 2BA, Condo! Free Pool, WIFI

A well-lit bedroom features a spacious bed with white linens and decorative pillows. A wooden nightstand is positioned beside the bed. A large mirror reflects the space, and natural light enters through a window, highlighting the calming light green walls.

4.97 out of 5 average rating, 35 reviews

Elegant Golf Front Condo w/ King, Walk to Village

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.

4.93 out of 5 average rating, 81 reviews

Charming Pinehurst Golf Front Condo