Holiday rentals with outdoor seating in Pinehurst

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.

4.98 out of 5 average rating, 156 reviews

The Ross Retreat - In Pinehurst

Your entire group will enjoy this central location to 40+ golf courses in Moore county with easy access to restaurants and close to grocery stores. This gorgeous home with custom woodwork and backyard oasis is the perfect retreat for families and golfers alike. Enjoy comfortable beds with down pillows and high end mattresses with mattress pads and a fully stocked kitchen in this newly furnished home. If you appreciate the little things like HEPA air filters and quite dishwashers, we got you.

4.95 out of 5 average rating, 261 reviews

* Top Rated - Guest Fave - Golf Front Condo *

Welcome to the heart of Pinehurst! This clean and cozy ground-floor condo is ideal for golf trips, weekend getaways, or longer stays. Enjoy a well-stocked kitchen, comfortable furnishings, and a screened porch with peaceful fairway views - couldn't be more perfect for morning coffee or evening wine! Super close to the Village, A+ dining and shops, the Fair Barn, harness track and Pinehurst Resort; just 10–15 minutes to Southern Pines and Aberdeen. Quiet, walkable, and always a guest favorite!

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, 148 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, 140 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.

4.97 out of 5 average rating, 237 reviews

A cozy sitting area is highlighted by a green sofa with accent pillows. A round wooden coffee table is positioned on a textured orange rug, while a colorful geometric wall provides a vibrant backdrop. A television and air conditioning unit are visible in the space.

Home in Southern Pines

Loft Cottage on Ridge Short & Extended Stays

This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. It is located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This loft unit has a private entrance from the top of the stairs with 1 bedroom (Queen) & 1 bath, a full kitchen, and shared laundry room downstairs in the back of the home. Unit features vintage kitchen! Come stay with us for a short stay or extended stay!

Guesthouse 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, 262 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, 838 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.

4.99 out of 5 average rating, 115 reviews

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

A golf front great view 3 BR 2 Bathrooms with furnishings bungalow situated on Pinehurst #6. This house comes with WIFI and 4 smart TVS (Spectrum cable with golf channel). All 4 beds (1 K, 1 Q, 2 double) are with memory foam mattresses. sofa set, dining table for 8, 55'' smart TV on the wall and washer/dryer combination. Enjoy relaxing on the deck after a great round of golf. Amenities include a full kitchen, coffee maker, cookware, microwave, refrigerator.

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, 306 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, 2 local breweries and wine shops. We also offer housekeeping for only $ 10 a day. PLEASE LET ME KNOW, when booking IF YOU NEED THE SECOND BED.

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.

4.97 out of 5 average rating, 137 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!

A comfortable living room features a brown leather sofa, black-accented chairs, and a rustic coffee table on wooden flooring. Golf-themed decor is displayed on the wall, while light enters through nearby windows, enhancing the welcoming ambiance.

5 out of 5 average rating, 153 reviews

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

Enjoy your stay at a fully renovated 2BR/2BA condo right across from Pinehurst's historic Fair Barn and Harness Track. Situated on No. 5, a short approach shot from the Pinehurst Clubhouse, the Duffer's Drop has everything you need for your golf getaway. Relax on the porch overlooking No. 5, work on your culinary skills in the beautiful kitchen, or just catch some rest between rounds. The Duffer's Drop is the exactly what you're looking for!

A bright living space is presented with a gray couch adorned with yellow cushions, accompanied by a round wooden dining table with black chairs. Natural light streams in through large windows, with decorative elements such as woven wall art and a potted plant adding a touch of warmth.

4.94 out of 5 average rating, 301 reviews

Fairway to Heaven - 2BD 2BA Golf Front Condo

Welcome to Fairway to Heaven, located within walking distance of the Pinehurst clubhouse and Village of Pinehurst! With a second story view on the Pinehurst #3 course, guests can enjoy hours of relaxation on the balcony overlooking the fairway, or stroll down to the historic Village for a cocktail, dinner or shopping. A 5 minute drive to the Fair Barn and Harness Track and a 10 minute drive to charming downtown Southern Pines.

Popular amenities for Pinehurst outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A cozy bedroom interior features a queen bed adorned with fresh linens and stacked towels. Natural light enters through a window, illuminating the warm-toned decor and subtle artwork above the headboard.

4.97 out of 5 average rating, 134 reviews

Cozy Pinehurst Retreat w/ Putting Green

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, 114 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

A single-story home is surrounded by tall pine trees and a lush green lawn. A well-maintained pathway leads to the front door, which is flanked by large windows. The house features a neutral exterior, and parking is available beside the entrance.

4.94 out of 5 average rating, 34 reviews

Pinehurst Golf Palace

A comfortable outdoor seating area is highlighted by a modern fire table, creating a cozy environment. The surrounding greenery adds a touch of nature, while the seating invites relaxation. The deck's wooden floor complements the overall aesthetic.

4.9 out of 5 average rating, 67 reviews

Quiet Pinehurst Golf Home | Pet-Friendly 3BR

The exterior of the home features a welcoming facade with a combination of siding and stone accents. A spacious driveway leads to a two-car garage. Two chairs are positioned on the porch, surrounded by landscaped greenery and a fenced yard.

4.98 out of 5 average rating, 117 reviews

The 19th Hole- a Pinehurst retreat for golf lovers

5 out of 5 average rating, 125 reviews

The modern kitchen features white cabinetry and stainless steel appliances, with an inviting dining table set for four. Natural light fills the space, showcasing an open layout that connects to the living area, highlighted by a comfortable seating arrangement and a stylish light fixture.

Home in Aberdeen

Spacious 4 BD Home with Game Room!

Home in Downtown Southern Pines

A small outdoor patio is presented with a round table and four black metal chairs. Lush greenery surrounds the area, providing a calm setting. The exterior of the cottage is gray, complemented by a dark front door and a welcoming pathway leading to the entrance.

4.96 out of 5 average rating, 217 reviews

Charming Cottage in Downtown Southern Pines

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.

4.97 out of 5 average rating, 200 reviews

Boutique-Style Pet-Friendly Horse Farm | Fox Den

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, 87 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.

4.82 out of 5 average rating, 11 reviews

The Pinehurst Perch

Apartment in Southern Pines

5 out of 5 average rating, 3 reviews

The Fairway at Talamore

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

4.74 out of 5 average rating, 43 reviews

Slice of Seclusion in Downtown 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, 16 reviews

Pinehurst Pied-à-Terre

Apartment in Southern Pines

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.

4.97 out of 5 average rating, 100 reviews

Private&Comfortable Studio for 2 in Southern Pines

Condo rentals with outdoor seating

5 out of 5 average rating, 21 reviews

A serene bedroom features a spacious bed dressed in neutral tones, complemented by a nature-inspired accent wall of tall trees. Bedside lamps add soft lighting, and a wooden nightstand is positioned beside the bed. A light area rug covers the floor, enhancing the calming ambiance.

Condo in Jackson Springs

Par In The Pines

5 out of 5 average rating, 12 reviews

Golf Retreat on Fairway Pinehurst #3 | Near Cradle

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, 96 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, 31 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, 117 reviews

Greenside Getaway️! Walk to Clubhouse and Cradle!

A wooden guest book with an engraved tree design is displayed on a dark tabletop. Next to it, a framed illustration of a scenic landscape adds a touch of charm. The setting is accented by soft natural lighting from nearby windows.

4.97 out of 5 average rating, 59 reviews

Fore on No. 5

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, 90 reviews

Charming Pinehurst Golf Front Condo

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.