Vacation rentals in Southern Pines

Guest suite in Downtown Southern Pines

4.95 out of 5 average rating, 107 reviews

The Century Suite - Upscale Comfort

Situated in the heart of Downtown Southern Pines, my private entrance suite is a cozy, upscale haven for those seeking convenience and comfort. Located on a quiet street, it’s only a block away from great restaurants and shops and easily walkable to all local hotspots. It’s perfect for those prioritizing location and comfort. The suite provides a comfortable bed, kitchenette and a big tub with provided bath bombs to soak in after a day of golfing, working, exploring town, or serving our country.

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.

4.96 out of 5 average rating, 105 reviews

Private&Comfortable Studio for 2 in Southern Pines

Enjoy a peaceful stay in this fully furnished studio for two, located in a quiet Southern Pines neighborhood. Atch. to the main house but fully soundproofed w/ a double wall, it offers a private key code entrance, queen bed, and a kitchenette w/ a hot plate and griddle. Step outside to your own private area with a fire pit. Just minutes from shopping, restaurants, breweries, golf courses, and movies. Only 15mins to the hospital, 20mins to Rockingham Racetrack, and 9mins to the Walthour Moss Fdtn

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, 122 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.

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, 397 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 15 min to the famous Pinehurst Resort and Carolina Horse Park. Features a King size Nectar bed, Roku TV, WiFi, shower with tankless water heater, a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge, 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!

4.92 out of 5 average rating, 246 reviews

A spacious living area features a large L-shaped sectional sofa in soft brown fabric, arranged on a patterned area rug with floral designs. A ceiling fan hangs above, and the adjoining kitchen can be seen in the background, equipped with dark wooden cabinets and stainless steel appliances.

Cottage in Pinebluff

Lakeside Cottage nestled near Pinehurst and CHP

Bellago Farm Cottage is nestled in the woods off the edge of the North Carolina Game Lands. It is 6 miles from the Carolina Hotel/Pinehurst Resort and the famous Pinehurst #2 Golf Course, and 8 miles from the Carolina Horse Park. The lakeside cottage welcomes you to fishing and swimming its spring-fed 9-acre, very clear waters. Enjoy relaxing between activities with easy access wi-fi or tv. If you are traveling to the area for equine competition, horse boarding is available.

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, 107 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.

Superhost

The kitchen features a large wooden island with a rustic design, surrounded by modern white cabinetry and stainless steel appliances. Abundant natural light filters through multiple windows, highlighting the wood beams above and the warm, welcoming atmosphere. A cozy seating area is visible in the background.

Cottage in Pinehurst

4.91 out of 5 average rating, 324 reviews

Water Oaks Cottage - Near Pinehurst Country Club

Three blocks by foot, bicycle or golf cart from the Carolina Hotel, deemed in 1901 the “Queen of South”, with its fine dining, entertainment, highly acclaimed “Spa at Pinehurst”, restaurants and shops of Pinehurst Village. Straight down from this grand resort by lovely promenade is the world-famous Pinehurst Country Club and renown “Number 2” championship golf course. A few blocks further, the 111 acre equestrian facility and historic Pinehurst Harness Track.

Cottage in Southern Pines

A welcoming living area features a blue couch adorned with yellow pillows, complemented by a round ottoman. A small dining table is positioned nearby, and large windows allow natural light to fill the space. A light fixture hangs above, enhancing the room's comfortable ambiance.

4.97 out of 5 average rating, 216 reviews

Cottage on Ridge -Short & Extended Stays

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

The charming exterior features a welcoming porch with an American flag hanging prominently. Two rocking chairs are positioned invitingly. Lush greenery surrounds the home, and stacked firewood is neatly arranged beside the entrance. A pathway of gravel leads up to the front steps.

5 out of 5 average rating, 111 reviews

Cozy Cottage - pet friendly, great location!

Enjoy a cozy and premium experience at this centrally-located place. Two minute drive to the Southern Pines downtown area, 15 minutes to Pinehurst, and just minutes from horse country. We have everything you need to have your dream stay in the Pines. Tons of amenities including: Fenced in backyard Outdoor patio with fire pit and grill Wood fireplace Smart TV Washer and dryer Desk workspace Fast WiFi Smart Thermostats 2 car driveway Full kitchen …and more!

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

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.

Bungalow in Downtown Southern Pines

The charming 1930's bungalow is framed by a white picket fence and flowering shrubs. A front porch is visible, inviting guests to enjoy the outdoors. Colorful blooms and greenery enhance the welcoming atmosphere, while a paved walkway leads to the entrance.

4.97 out of 5 average rating, 392 reviews

Delightful Bungalow 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, quaint & cozy 1930's bungalow. Just steps from our idyllic downtown of Southern Pines. (Literally 1 block!) You will be treated to a private, clean, cozy and updated space filled with everything you will need for a wonderful stay. 1 bedroom / 1 bath / 1 sleeper sofa. Street parking. Strict 'No Pet' policy.

4.99 out of 5 average rating, 125 reviews

A wooden deck offers a view of lush green fields and tree-lined pastures. A well-maintained dirt path curves through the landscape, bordered by wooden fencing. The sky is partly cloudy, providing a serene backdrop for the surrounding country setting.

Apartment in Vass

Horse farm apartment - 1 bedroom

Located in Moore county 'horse country'. The apartment is above a barn, in the heart of an equestrian community. We welcome you if you are traveling with your horse or visiting the Southern Pines, Pinehurst, or the Ft. Bragg area. It is an easy 9 mile drive to Southern Pines, 11 miles to Woodlake Country Club, 12 miles to downtown Pinehurst, and 17 miles to Fort Liberty.

Popular amenities for Southern Pines vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Southern Pines

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, 60 reviews

19th Hole - Pickelball, Park, Walk to Downtown

4.94 out of 5 average rating, 17 reviews

Convenient Cottage in the Pines

Apartment in Downtown Southern Pines

A living area showcases a comfortable brown sofa paired with a woven armchair. A coffee table sits at the center, complemented by decorative items. Natural light streams through the window, illuminating the white mantel with a modern television on top. Light hardwood flooring enhances the warm ambiance.

4.86 out of 5 average rating, 161 reviews

Belleview on Bennett, Heart of Downtown So Pines!

Home in Downtown Southern Pines

A charming two-story cottage is featured in the image, showcasing light blue shingles and a welcoming front porch with rocking chairs. The pathway is bordered by landscaping, leading up to the entrance. Natural light filters through the trees, creating dappled shadows on the ground.

5 out of 5 average rating, 54 reviews

Newly remodeled Downtown Cottage-walking distance

4.9 out of 5 average rating, 69 reviews

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.

Home in Pinehurst

Quiet Pinehurst Golf Home | Pet-Friendly 3BR

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.

4.94 out of 5 average rating, 65 reviews

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

4.9 out of 5 average rating, 50 reviews

A spacious living area features a comfortable blue sofa and a recliner, complemented by a large wooden coffee table. Natural light enters through oversized windows, illuminating the room's neutral decor and hardwood flooring. A TV unit and decorative plants enhance the inviting environment.

Home in Pinehurst

cheerful 4 bedroom cottage in perfect location

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.