House holiday rentals in Southern Pines

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, 111 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, 200 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 are centrally located just 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 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.

4.98 out of 5 average rating, 127 reviews

Cozy Pinehurst Retreat w/ Putting Green

Enjoy your Pinehurst stay in the family-friendly neighborhood of Village acres. The area is surrounded by The Greenway pedestrian and bicycling trail. The house is situated within 2 miles of downtown Pinehurst, Camelot Park, and Rassie Wicker Park, and is a short drive away from any of the many wonderful golf courses that Pinehurst has to offer. It was recently remodeled, is well furnished, and we are constantly striving to upgrade and improve the space to make for a comfortable stay!

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, 221 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!

4.98 out of 5 average rating, 818 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, 104 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, 212 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, 100 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, 120 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.

Popular amenities for Southern Pines house rentals

Kitchen

Wi-Fi

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

An open-plan living area features a spacious dining table surrounded by six upholstered chairs. A modern kitchen with an island is visible, showcasing new appliances and sleek countertops. Natural light streams in through windows, highlighting the warm wood flooring and neutral wall colors.

4.9 out of 5 average rating, 20 reviews

25 McQueen - 4 Bedroom House 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.

An inviting outdoor space features a private pool surrounded by a concrete deck. Two lounge chairs are positioned under a large umbrella. A round table holds a decorative arrangement, while a pink inflatable float is visible in the pool.

4.92 out of 5 average rating, 38 reviews

Gorgeous Home | Private Pool | Close to Pinehurst

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, 79 reviews

Southern Pines Getaway - Pool, Hot Tub & Fire Pit

A private backyard pool area is illuminated softly under a twilight sky. Landscaped with lush shrubs and flowers, the scene features a swimming pool surrounded by a stone pathway and solar lights. The covered seating area and flag gently sway in the evening breeze.

5 out of 5 average rating, 46 reviews

The Pinehurst Paradise Pool Home

Weekly house rentals

Superhost

Home in Moore County

5 out of 5 average rating, 4 reviews

Pinehurst Grand Slam! Unbeatable rates in VoP!

A game room with dark green walls features a large golf simulator screen displaying a scenic golf course. A spacious sectional couch in a warm yellow hue provides comfortable seating, while a dartboard and additional TV are visible on the walls.

5 out of 5 average rating, 33 reviews

NEW 6BR w/ Golf Sim Hot Tub Sauna Game Room

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 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, 70 reviews

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

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, 61 reviews

Pinehurst No.6 Townhouse

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

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.

4.98 out of 5 average rating, 57 reviews

Stunning Southern Pinehurst Home! Close to Village

A spacious game room features a pool table at the center, surrounded by comfortable seating. Large windows provide ample natural light and views of the lush outdoors. A dartboard and arcade games are placed against the walls, enhancing the recreational environment.

5 out of 5 average rating, 16 reviews

House on Fairway at Pine Needles

Private house rentals

The charming cottage is surrounded by lush trees, featuring a white brick exterior and a welcoming arched entrance. The roof has a gentle slope, complemented by symmetrically placed windows. A stone pathway leads to the front door, enhancing the natural setting.

5 out of 5 average rating, 58 reviews

NEW BUILD Golf Cottage-Perfect for Couples/Family

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, 78 reviews

Ivy Kirk Cottage in the Village of Pinehurst

A modern kitchen features sleek white cabinetry, a marble backsplash, and stainless steel appliances. The floor is adorned with intricate patterned tiles. A small dining set with two chairs is positioned near a window, allowing natural light to illuminate the space.

5 out of 5 average rating, 10 reviews

2 Mstr King Suites • Lux Kitchen• Games • Location

A modern farmhouse is presented, featuring a welcoming white exterior paired with natural stone accents. Large windows enhance the exterior, and a covered porch with a railing invites relaxation. Lush green landscaping surrounds the house, offering a peaceful and spacious setting.

4.99 out of 5 average rating, 94 reviews

5 BR New Build! 5min to Golf & Village + Game Room

A comfortable living room is presented, featuring a blue sofa with decorative pillows and a beige armchair. A round coffee table sits in front, with a soft area rug underneath. A painting adorns the wall, and natural light illuminates the space.

5 out of 5 average rating, 24 reviews

Slice of Southern Heaven! Serenity Pines Cottage

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

A game room features a shuffleboard table with a polished wood surface and a modern green cabinet. Two leather armchairs provide comfortable seating. Framed artwork adorns the walls, alongside a bright neon sign displaying 'Pinehurst.' Natural light filters through the window.

5 out of 5 average rating, 61 reviews

Sunny Pinehurst Retreat

A well-maintained putting green is framed by lush greenery and features multiple holes with small flags. Seated patio furniture occupies the adjacent deck, providing a view of open space and trees under a partly cloudy sky.