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)

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, 146 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.

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.

5 out of 5 average rating, 205 reviews

A soothing hot tub is illuminated by soft blue lights, creating a calming ambiance. The surrounding area features a modern privacy screen, subtly highlighted by exterior lighting, enhancing the serene nighttime setting.

Home in Pinebluff

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay and Play Retreat! We’re centrally located minutes away from some of the areas greatest attractions such as Pinehurst No. 2 (8 Miles), Rockingham Dragway (14 miles), Carolina Horse Park (10 miles), and Fort Bragg (16 miles) . We're also surrounded by many beautiful golf courses including Legacy Golf Links and a wide variety of dining options within 11 miles of this completely renovated home that has been created specifically for your comfort, relaxation & enjoyment.

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.

Popular amenities for house rentals in Southern Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

Superhost

A spacious living area features a large flat-screen TV mounted above a wooden mantel. Two light gray sofas are arranged around a rustic coffee table adorned with a small floral centerpiece. Natural light streams through multiple windows, highlighting the inviting atmosphere.

Home in Foxfire

4.59 out of 5 average rating, 17 reviews

Luxurious Pine Manor: Golf Front Estate with Pool!

A fire pit surrounded by rustic Adirondack chairs is positioned on a stone patio. Soft glowing lights hang from a nearby tree, illuminating the tranquil atmosphere. In the background, a heated pool is visible, reflecting the serene night sky.

5 out of 5 average rating, 18 reviews

Walk to Village: Heated Pool Hot Tub Putting Green

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

5 out of 5 average rating, 13 reviews

Charming Downtown Corner Cottage - Dog Friendly!

Superhost

A light-filled living area features a comfortable grey couch adorned with decorative pillows, complemented by a cozy armchair. Artwork is displayed on the walls, and soft lighting is provided by two table lamps beside the seating. A flat-screen TV is situated within the media console.

4.81 out of 5 average rating, 26 reviews

Pinehurst Choice

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, 91 reviews

Cheerful Eclectic Pinehurst home

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.

A cozy living area presents a plush couch complemented by two brown leather chairs. A round coffee table sits in the center, with a potted orchid adding a touch of nature. Soft light filters through the windows, enhancing the room's inviting ambiance.

4.98 out of 5 average rating, 98 reviews

Peaceful Home Near Pinehurst | Quiet Neighborhood

A spacious living area is illuminated by natural light from skylights and large windows. A comfortable gray sofa is central, surrounded by two brown accent chairs. A wooden coffee table sits on a patterned area rug, complemented by a TV and natural greenery.

4.97 out of 5 average rating, 96 reviews

Modern Golf Home in Pinehurst - 5 Min to Courses

5 out of 5 average rating, 34 reviews

A cozy living area is furnished with a dark sectional sofa, a circular glass coffee table, and a decorative lamp. Light wood paneling and large windows provide natural light. A wooden ladder leads to a lofted sleeping area, while a potted plant adds a touch of greenery.

Home in Vass

House in the Pines

Private house rentals

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 charming yellow cottage is framed by lush greenery and a low fence. The front porch is visible, featuring two chairs that invite relaxation. A blue sky with scattered clouds adds to the serene outdoor atmosphere, while shrubs and trees enhance the privacy of the yard.

4.92 out of 5 average rating, 13 reviews

Cottage Home in Southern Pines

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

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!

4.83 out of 5 average rating, 24 reviews

The exterior of a single-story home is presented, featuring a light grey façade and a spacious driveway. A two-car garage is visible, along with manicured landscaping that includes shrubs and a small tree. The surrounding area consists of tall green trees under a clear blue sky.

Home in Aberdeen

Golfers Serene Getaway

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 private golf studio is showcased, featuring a large projection screen displaying a golf course view. The room is illuminated by soft lighting around the edges, with a green turf floor mimicking a putting green and a small desk setup in the corner.

5 out of 5 average rating, 71 reviews

Luxe Golf Simulator, Golden Tee, Hot Tub, Views!