Vacation rentals in Southern Pines

Cottage in Southern Pines

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, 357 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 less than 15 min to the famous Pinehurst Resort. Features a King size Nectar bed, Fire TV, WiFi, shower with tankless water heater a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge w/ freezer, toaster oven, 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!

Farm stay in Southern Pines

An outdoor seating area is showcased, featuring two armchairs and a matching coffee table. The chairs are equipped with navy cushions, each adorned with decorative blue patterned throw pillows. The setting is complemented by a white wall and a door with geometric designs behind the furniture.

4.99 out of 5 average rating, 179 reviews

Finally Home Farm Bed and Barn

Bring your horse and your golf clubs! Welcome to Finally Home Farm Bed and Barn! A private 1 bedroom barn converted into a quaint cottage. Located on a peaceful farm just 2 miles from downtown Southern Pines, 1 mile from the back gate of Ft. Bragg and next to Weymouth Woods State Park, Finally Home Farm is the perfect place to explore all the Sandhills has to offer. *We are horse ($40) and dog friendly ($50) pet fee with Pre-Approval. Please include this info in your pre-booking.

4.93 out of 5 average rating, 180 reviews

A modern bathroom is showcased with a sleek countertop featuring a white vessel sink. Dark cabinetry complements the light-colored wall. A large mirror above the sink reflects the space, while decorative greenery adds a touch of freshness.

Condo in Southern Pines

Relaxing in the Pines

Located 5 min from downtown Southern Pines (Broad St). A great place to stay for golfers, horse lovers, and others visiting to explore Pinehurst, Southern Pines and other surrounding areas. The large screened in porch off of the living room and dinning room which provides peaceful beauty and elegance. Two bedrooms and two full baths, this condo provides you with a wonderful opportunity for anyone wanting to relax and especially for golfers, horse lovers and others..5 PM Check in

The entrance features a covered porch with two comfortable rocking chairs placed on either side of a decorative front door. Wall-mounted lights illuminate the entryway, while a brick step leads up to the porch. A garage door is also visible on the left.

4.94 out of 5 average rating, 105 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!

The Tudor Revival Carriage House is set amongst tall Longleaf Pines, with warm lighting emanating from its windows. The structure features a gravel driveway, dual garage doors, and is complemented by lush greenery around its perimeter.

4.98 out of 5 average rating, 242 reviews

Historic Southern Pines Carriage House

Just minutes from Pinehurst and only one mile from downtown Southern Pines, this Tudor Revival Carriage House keeps you close to golf and activities! Enjoy a peaceful setting surrounded by an acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Enjoy area golf courses or stop in when visiting Penick Village, the Carolina Horse Park or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO PARTIES.

A welcoming outdoor seating area is displayed with striped chairs arranged on a wooden deck. Ferns hang from the ceiling, framing a view into the cozy dining area, where warm light is provided by a table lamp. The open floor plan enhances the inviting space.

4.94 out of 5 average rating, 208 reviews

Mystical Cottage

A warm cozy guest house with an open floor plan, high ceilings, and a wall of glass doors overlooking the pool and jungle like backyard of 3 acres. It has a large separate bath and complete kitchen. It was a perfect place for a completely secluded getaway ... less than 2.5 miles from the center of both Southern Pines and the Village of Pinehurst... 8 minutes from nearly every restaurant in the area. We are pet friendly, but charge a seperate $35 pet cleaning pet.

Guest suite in Southern Pines

The image showcases a wooden dock leading to a serene lake surrounded by dense greenery. The calm water reflects the overcast sky, with lily pads visible on the surface. Trees line the shore, contributing to the tranquil natural setting.

4.96 out of 5 average rating, 245 reviews

Golf Resort, Private Entrance, Bath & Kitchenette

This Condo is located on Talamore Golf Resort and is minutes away from many world class golf courses, to include Pinehurst Resort. Approximately 40 minutes to Fort Bragg for Military/DOD civilians who are TDY or house hunting; 4 miles to First Health Moore Regional Hospital for travel nurses; 2.5 miles to Sandhill community college; Reservoir Park is a 250 yard walk from the front door and includes a 95 acre lake, and more than 12 miles of Greenway Trails.

Cottage in Southern Pines

A welcoming entryway features a patterned area rug, wooden flooring, and a side table adorned with a lamp and decor. A mirror hangs on the wall, and a plant adds a touch of greenery. Light fills the space through nearby windows.

4.97 out of 5 average rating, 185 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!

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, 204 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.

Apartment in Southern Pines

A child is seen crouching on the ground amidst several chickens. The setting features natural brown pine needles and short grass. The chickens, in shades of golden yellow, roam freely nearby, creating a lively scene on the farm.

4.96 out of 5 average rating, 196 reviews

Tanglewood Farm B&B Horse Farm- The Fox Den Suite

Welcome to the Fox Den Suite at Tanglewood Farm! The Fox Den is a private one bedroom (KING) , one bathroom beautifully decorated apartment on our beautiful 10 acre horse farm. Nestled in the heart of North Carolina's beautiful horse county, just minutes from charming downtown Southern Pines. Enjoy local breweries, shops, amazing restaurants and over 100 beautiful golf courses. Weekend Breakfast for Two Sat and Sun Avail for Purchase at $30/morning

4.97 out of 5 average rating, 181 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!

Bungalow in Southern Pines

4.97 out of 5 average rating, 326 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.

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Popular amenities for Southern Pines vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Southern Pines

A gravel driveway leads towards a peaceful wooded area, bordered by lush green trees. The sunlight filters through the leaves, creating a serene environment. A cozy home is partially visible on the left side of the image, with soft-colored siding and a chimney.

5 out of 5 average rating, 61 reviews

Quiet and Safe neighborhood Studio for 2

A clear sign marked 'Cottage Parking Only' stands on a post, positioned in a grassy area beside the cottage. Nearby, soft landscape lighting is visible along the pathway. The background includes a privacy fence and greenery, ensuring a serene setting for parking.

5 out of 5 average rating, 29 reviews

The Kensington Cottage

4.95 out of 5 average rating, 64 reviews

SoPi Oasis | Hot Tub | Fire Pit | Game Room | Pets

Guest suite in Southern Pines

A brick pathway leads to a gated entrance, framed by lush greenery and towering trees. The well-maintained garden features low shrubs and a serene atmosphere, providing a welcoming entry point to the property. The surrounding natural elements enhance the sense of privacy.

4.96 out of 5 average rating, 53 reviews

Charming Guest Suite in SoPi

A clean and modern bathroom features a white bathtub, accompanied by a sleek marble-patterned wall. A shower curtain is partially drawn, revealing a showerhead and a storage rack with toiletries neatly arranged. Light reflects gently off the glossy tiles.

4.94 out of 5 average rating, 18 reviews

Cute cottage close to downtown Southern Pines

5 out of 5 average rating, 13 reviews

A wooden deck is depicted, featuring a small table and two chairs. The entrance door is painted in a soft blue shade, complemented by a large window that allows natural light to fill the space. Lush greenery is visible in the background, enhancing the inviting atmosphere.

Loft in Southern Pines

Slate at The Shire 255 - Unit C - Downtown!

An outdoor dining setup is presented in soft evening light, featuring a rustic wooden table set with plates and candles. Two lanterns add ambiance alongside a cozy seating area with cushions. The surrounding space is adorned with potted flowers and hint of greenery.

4.99 out of 5 average rating, 92 reviews

The Gallery - 2 bd Boutique Southern Pines Cottage