Vacation rentals in Southern Pines

Apartment in Southern Pines

A kitchenette is displayed, featuring modern cabinetry and a countertop. Stainless steel appliances, including a refrigerator, are visible. Counter space is organized with tableware, and a decorative mirror enhances the area. A framed artwork adds a touch of elegance to the space.

4.96 out of 5 average rating, 109 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

A spacious living room features a cozy seating arrangement with light brown leather sofas and two dark armchairs. A flat-screen television is mounted above a decorative fireplace. Natural light streams in through sliding glass doors, leading to an outdoor deck with additional seating options.

5 out of 5 average rating, 127 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 charming tiny cottage features a covered porch with steps leading to an intricately designed stone patio. Surrounding landscaping includes mature greenery and carefully placed decorative shrubs. A grill is positioned nearby, providing additional outdoor cooking options in a serene setting.

4.96 out of 5 average rating, 411 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!

Home in Downtown Southern Pines

A charming two-story cottage is presented with a white exterior and a black roof. A sunroom with large glass panels is visible at the front, while neatly trimmed shrubs and landscaped gardens enhance the inviting entrance.

4.98 out of 5 average rating, 113 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.

The exterior of the DownTown Ace features a welcoming two-story structure with a dark gray roof and light gray siding. Lush green lawns are surrounded by mature trees, creating a serene environment. The entrance is framed by brick accents and a pathway leading to the front door.

4.93 out of 5 average rating, 98 reviews

The Downtown Ace

The DownTown Ace is just under a mile from downtown Southern Pines, offering easy access to a variety of golfing and dining options. We take pride in creating a welcoming space with luxury amenities designed for your comfort. Enjoy a fully equipped kitchen, a well-stocked coffee bar, premium toiletries upon arrival, family-friendly games, a queen-size air mattress, and much more! Our goal is to make you feel like you've stepped into your home away from home.

An airy living space features hardwood flooring, a patterned area rug, and a green decorative plant. The room is separated from a cozy sitting area, which includes a blue couch and a side table with a lamp. Light filters through sheer window treatments.

4.97 out of 5 average rating, 222 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!

An open living space features modern furnishings with a comfortable sofa, accent chairs, and a coffee table. A dining area seats six, complemented by a kitchen island with additional seating. Large windows provide natural light, and a ceiling fan circulates air above.

4.92 out of 5 average rating, 111 reviews

Golfer's Paradise I Modern I Charming I 3BED/2BATH

Ideal for tournament stays and multi-day golf trips! Centrally located between Pinehurst and Southern Pines Accommodating up to 6 guests in exceptional comfort, our 3-bedroom, 2-bath Charming Pines Hideaway is ideally located within walking distance of Pine Needles Lodge and Golf Club. The great location provides easy access to nearby golf, horseback riding, hiking trails, kayaking, restaurants, and downtown districts of the Pinehurst/Southern Pines area.

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, 115 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

The exterior of a cozy cottage is set within a lush green landscape, surrounded by tall trees. A white picket fence encloses the property, offering a sense of privacy. An inviting pathway leads to the front door, creating a charming entrance.

4.96 out of 5 average rating, 226 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.

4.97 out of 5 average rating, 229 reviews

Serene By the Greens

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!

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.

4.98 out of 5 average rating, 402 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.

Home in Downtown Southern Pines

A spacious living room features a sectional sofa and a single chair, arranged for comfort. Large windows with shades allow natural light. A sleek coffee table sits on a textured area rug, and a large television is mounted on an entertainment unit against the wall.

4.94 out of 5 average rating, 103 reviews

Historic Hidden Gem - Secluded Downtown Home

This special home is over 100 years old and nestled in historic downtown Southern Pines. Secluded on a private wooded lot just blocks from Broad Street, this incredibly space offers a unique combination of privacy and accessibility to local shops, breweries, and community events. Relax at the house and enjoy the comfortable screened in front porch or take a short walk to see all that Southern Pines has to offer!

Popular amenities for Southern Pines vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Southern Pines

A welcoming entryway features a wooden door framed by dark exterior walls. Two Adirondack chairs are positioned on a concrete porch, accompanied by a small welcome mat. A soft glow illuminates the space from overhead, adding to the inviting atmosphere.

5 out of 5 average rating, 64 reviews

19th Hole - Pickelball, Park, Walk to Downtown

5 out of 5 average rating, 62 reviews

The entrance of the cottage is framed by a stone facade and wood accents, showcasing a welcoming porch with two chairs. A landscaped pathway leads to the front door, surrounded by manicured lawns and trees providing shade.

Home in Pinehurst

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

An inviting dining area features a built-in bench seating arrangement alongside a table, illuminated by natural light streaming through a window. Grey walls and sleek appliances complement the modern design, creating a warm gathering space.

4.98 out of 5 average rating, 87 reviews

SoPi Cottage

The exterior of the quaint unit is showcased, featuring a gray facade with white trim. A welcoming entrance is visible, flanked by seating options on a wooden deck. Lush green grass surrounds the property, and a staircase leads to an elevated outdoor area.

4.92 out of 5 average rating, 53 reviews

Sage at The Shire 255 - Unit A - Downtown!

A secluded home is depicted with a spacious swimming pool in the foreground. The pool area features a surrounding deck and access to the house, which has a combination of windows and a chimney. Green trees line the property, enhancing the outdoor setting.

4.98 out of 5 average rating, 89 reviews

Southern Pines Getaway - Pool, Hot Tub & Fire Pit

5 out of 5 average rating, 11 reviews

Sweet Tee Cottage On The Greens

Apartment in Southern Pines

4.97 out of 5 average rating, 37 reviews

The Warren

A modern kitchen features a central island with seating for four. Stainless steel appliances are positioned along the walls, with cabinets above providing ample storage. A dining table for six is placed next to large windows that allow natural light to fill the space.