House holiday rentals in Southern Pines

The exterior of a single-story home is displayed, featuring a manicured lawn and a spacious driveway. Tall pine trees surround the property, providing shade and a natural setting. The house showcases large windows and subtle landscaping, inviting a sense of tranquility.

4.99 out of 5 average rating, 110 reviews

Comfy Pinehurst Home near Golf w/ Ping-pong

Life in the Pines! This charming home, only 1.4 miles from the Pinehurst Golf Clubhouse, provides ample space to relax and unwind. With easy access to Southern Pines, Aberdeen, golf, events, and great dining is the ideal place for a get away. A 3 bedroom, 2 bath, home with a spacious yard, outdoor dining, and a ping pong table, nestled in the tall pines and a quiet neighborhood provides something for everyone during their stay in the Pinehurst area. (Note: Cameras - doorbell and driveway)

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.

5 out of 5 average rating, 112 reviews

New 5 Bedroom Cottage on Pine Needles Golf Course

New construction home on the golf course of Pine Needles Course between Pinehurst and downtown Southern Pines. Ideal location, close to everything the area has to offer. This 5 bedroom and 3 bathroom cottage is ideal for golf outings and family friendly vacations. Everything you need to make your stay ideal and comfortable. Main level: 1 bedroom, 1 bath, living room, kitchen, dining, office space, walk in pantry, laundry room. Second floor: 4 bedrooms, 2 bathrooms, abundant closet space.

A comfortable living room features a flat-screen TV mounted on the wall, alongside a stylish electric fireplace. A blue sectional sofa and a dark gray loveseat provide seating options. Natural light enters through the window, accented by cheerful throw pillows and wall art.

4.93 out of 5 average rating, 187 reviews

The Pines - Cozy, Large Fenced Yard (Upper Unit)

Enjoy a quiet stay tucked back in beautiful pine trees, less than a mile from downtown So Pines! 10 minutes to Pinehurst resort, great patio and large fenced yard shared with the lower unit (pet friendly). This upper unit has a full kitchen, King bedroom with en suite bathroom, two Queen bedrooms, a second bath, an electric fireplace in the living room, and a private washer/dryer making this a perfect fit for a longer stay, too. This home has all the essentials for a great getaway!

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.

4.96 out of 5 average rating, 222 reviews

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!

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

Discover the perfect blend of personality and convenience at Bourbon on Bennett, a newly constructed gem in the heart of Downtown Southern Pines. Enjoy stylish furnishings, a fully equipped kitchen, and two spacious bedrooms with queen beds, including one en-suite bath. Just a short, easy walk to all the shopping, fine dining, cafes, restaurants, nightlife, and entertainment along Broad Street, Southern Pines. Enjoy the convenience of being right in the center of it all!

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, 821 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 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, 105 reviews

The Gallery - 2 bd Boutique Southern Pines Cottage

Enjoy a uniquely designed experience at this centrally-located place - whether in town for golfing, riding, or simply enjoying our quaint southern town. Just a block from Broad street's restaurants, shops, breweries and theatre, this two bedroom, two story cottage (and art studio!) has everything you need to enjoy Moore County. Relax in any of our carefully curated rooms, or take it outside to our backyard/vineyard for a summertime BBQ or a cozy fireside chat.

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, 213 reviews

Charming Cottage in Downtown Southern Pines

Right in Downtown Southern Pines, Camellia Cottage is the perfect getaway! Walking distance to all of the wonderful restaurants, shops and breweries Downtown Southern Pines has to offer, and only minutes from some of the country's best golf courses! This 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your own private patio, walk around and take in the beautiful sights of this charming Southern town.

The entrance to the home is framed by tall pine trees, showcasing a well-maintained path leading to a welcoming front door. A modern gate and house number are visible, enhancing the overall appeal of the property.

4.98 out of 5 average rating, 200 reviews

Golfers’ Mid-Century Escape Minutes From Pinehurst

Relax in this peaceful, newly renovated space with a modern touch. Located in a quiet neighborhood next to Hyland Golf Club, this home offers the perfect retreat for golf lovers. Just one exit north of Pine Needles golf course (3.9 miles), it’s ideally situated for those attending the US Kids Golf World Championship at Longleaf Golf Club (5.9 miles away) or the US Men’s Open at Pinehurst #2 (8.9 miles away). Secure your golf getaway now—book today!

A newly constructed three-story house features a modern design with a green exterior and white trim. The front porch is accessible by steps, and multiple large windows allow natural light to fill the interior. Surrounding landscaping includes trimmed shrubbery and grass.

4.97 out of 5 average rating, 101 reviews

Pet Friendly with Firepit Cottage Near Pinehurst

Brand new 3 bedroom 2.5 bathroom house, a perfect fit for 6 people. Close to Southern Pines and Pinehurst makes it easy to navigate around Moore County. This house is stocked with everything you need, whether you're here to have a good time golfing with friends, or on a trip to visit family. One king bed, one queen bed, and two twin beds, a configuration for any group. A pack and play is also in the house and ready for your little one.

An open living space features brick flooring, a cozy seating area with a sofa and armchair, and a wall of bookshelves filled with books. A television is mounted on the wall, and warm light is provided by lamps. A dining table and kitchen island are present, enhancing functionality.

4.98 out of 5 average rating, 122 reviews

Charming Retreat in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. This charming retreat is unique, eclectic and super cozy! Stay, enjoy and relax in the confines of which used to be a garage. This space features all brick floors, lots of windows with plantation shutters, books, a comfy bed, walk in tiled shower, kitchen and quite distinctive décor. Peruse the large selection of books and enjoy some reading during your stay.

4.98 out of 5 average rating, 120 reviews

Isle of the Pines! 1 mi. from Village of Pinehurst

Isle of the Pines is a family owned home with lots of thought put into the experience we want to offer our guests. We pride ourselves on the inviting space we provide through offering luxury amenities such as a fully equipped kitchen, abundantly stocked coffee bar, toiletries upon arrival, several family oriented games, and so much more!. We want you to feel like you have walked into your home away from home!

Popular amenities for house rentals in Southern Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a combination of comfortable seating, including a sleek sofa and armchairs. A modern coffee table sits atop a patterned area rug, with natural light filtering in through large windows. The open layout connects seamlessly to the kitchen area.

4.96 out of 5 average rating, 71 reviews

Cheerful Pinehurst home tucked away with a pool.

The image features a golf simulator area with a virtual course displayed on a large screen, complemented by a putting green. A spacious outdoor pool is visible, alongside a cozy living space with comfortable seating and decorative elements. The exterior shows a beautiful patio surrounded by lush greenery.

5 out of 5 average rating, 51 reviews

Simulator & Unbeatable Golf Experience On 2 Acres!

The exterior of the home is framed by tall pine trees, with a long driveway allowing ample parking space. The two-story house features a light-colored siding and large front windows. Neatly trimmed shrubs and flower pots enhance the inviting curb appeal.

4.98 out of 5 average rating, 93 reviews

This is it! | Pool | Golf | Convenient to Town

5 out of 5 average rating, 29 reviews

The spacious living area features large windows that allow natural light to fill the room. Comfortable seating is arranged around a substantial wooden coffee table, while a stone fireplace is set against a decorative wall. A warm, neutral color palette creates a relaxed setting.

Home in Aberdeen

Lakeside Escape - 5 Miles from Pinehurst Resort

4.93 out of 5 average rating, 123 reviews

A rectangular pool with clear blue water is surrounded by a concrete patio. A pool ladder is visible on one end. In the background, a structure with stairs and a mobile home can be seen, along with several tall pine trees providing shade.

Home in Aberdeen

Country living 10 mins to Horse Park, Golf & Town.

A spacious bedroom is furnished with a large bed featuring crisp white linens and decorative pillows. Soft lighting is provided by two bedside lamps. Natural light floods the room through sliding glass doors leading to a private outdoor space, framed by sheer curtains.

5 out of 5 average rating, 80 reviews

Southern Pines Getaway - Pool, Hot Tub & Fire Pit

5 out of 5 average rating, 46 reviews

The Pinehurst Paradise Pool Home

The entrance features a stone pathway leading to a welcoming front door adorned with a wreath. Potted plants flank either side of the entrance, and the surrounding greenery adds to the home's inviting exterior.

5 out of 5 average rating, 24 reviews

Spacious property w/Pool & walkable to downtown

Weekly house rentals

An open-concept living space features a large dining table set for meals, with modern wooden chairs. A comfortable sofa sits in the lounge area, while a stylish kitchen with dark cabinetry and high-end appliances is visible in the background. Ample natural light brightens the area.

5 out of 5 average rating, 48 reviews

19th Hole - Pickelball, Park, Downtown, Sim Access

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.

4.94 out of 5 average rating, 67 reviews

New Pines Retreat

A modern kitchen features white cabinetry and dark countertops, complemented by a long wooden dining table surrounded by several metal stools. An open layout is visible, connecting to a hallway with a glimpse of the living area and additional room.

4.96 out of 5 average rating, 51 reviews

The Oakmont Cottage

A spacious living area features high ceilings and floor-to-ceiling windows providing ample natural light. Comfortable seating includes two plush armchairs and a cozy sofa, arranged around a coffee table. A gas log fireplace is positioned beneath a wall-mounted TV, creating a welcoming atmosphere.

5 out of 5 average rating, 52 reviews

Million $ Golf-front view + 3 Master BR + Peloton

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, 32 reviews

Pinehurst Golf Palace

A spacious living area is furnished with a light grey sectional sofa and a decorative leather ottoman. Natural light filters through two windows adorned with white blinds, complementing a potted plant and wooden chairs in the background. A subtle area rug adds warmth to the wooden floor.

4.82 out of 5 average rating, 28 reviews

The McCaskill Cottage in the Village of Pinehurst!

A spacious backyard features a 400 square foot putting green, surrounded by well-maintained grass. Decorative string lights illuminate the area, which includes a sitting area with red chairs and a patio table. A golf bag rests beside the putting green, adding a recreational touch.

5 out of 5 average rating, 23 reviews

NEW Putting Green | 5 Mins to Pinehurst | Sleeps 8

An inviting backyard space features several blue Adirondack chairs arranged around a stone fire pit. The house, sporting a yellow exterior, is visible in the background, complemented by lush greenery and a clear area for outdoor activities.

4.93 out of 5 average rating, 57 reviews

Downtown So. Pines - sleeps 8, walk to town.

Private house rentals

4.93 out of 5 average rating, 40 reviews

An open living area displays a spacious sectional sofa adorned with yellow pillows, inviting relaxation. A dining table for four is positioned in the corner, while a modern kitchen, featuring stainless steel appliances and white cabinetry, is visible in the background.

Home in Carthage

Sandhills Getaway!

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.

4.98 out of 5 average rating, 80 reviews

Ivy Kirk Cottage in the Village of Pinehurst

A dining area features a large black table surrounded by eight cushioned chairs. Light streams through multiple windows, illuminating the space. A modern pendant light hangs above the table, while a potted plant adds a touch of greenery to the welcoming atmosphere.

4.97 out of 5 average rating, 33 reviews

Timeless Tudor - Walkable to Downtown!

The wrap-around deck is lined with wooden bar-height chairs, providing comfortable seating. Soft ambient lighting hangs above, creating a relaxed atmosphere. Views of the surrounding trees and neighboring buildings are visible, enhancing the outdoor experience.

4.87 out of 5 average rating, 62 reviews

Pinehurst No.6 Townhouse

A cozy living room is showcased with a large sectional sofa and a colorful area rug. A 52" Smart TV is positioned on a stylish cabinet. Bright artwork adorns the walls, and a ceiling fan provides comfort. An inviting entryway leads to the home.

4.95 out of 5 average rating, 38 reviews

Sweet Retreat w/ Firepit, Near Downtown & Golf

5 out of 5 average rating, 62 reviews

Sunny Pinehurst Retreat

A single-story brick home is surrounded by tall pine trees, with vibrant landscaping visible in the front yard. A gravel driveway leads to a two-car garage, and a layer of pine needles covers the ground, adding texture to the outdoor space.

5 out of 5 average rating, 13 reviews

Starlit Pines - 5 minute drive to Pinehurst Resort

The exterior of the home showcases a well-maintained yard with lush green grass and mature trees. A stone façade is complemented by a welcoming front porch featuring two chairs. Garage access is visible on the right, framed by neatly trimmed shrubs.