Vacation rentals in Southern Pines

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, 359 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

The exterior of the cozy barn cottage features a brick facade and white paneling, complemented by a shaded porch with seating. Two stable doors are visible, surrounded by lush greenery and tall trees, creating a serene country atmosphere.

4.99 out of 5 average rating, 181 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, 181 reviews

A golf course view is framed by tall pine trees, offering a serene landscape of green grass and a sand trap. The open space features soft shadows cast by the trees, creating a natural setting for relaxation.

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

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.

4.94 out of 5 average rating, 106 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, 244 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.

The guest house features a bright exterior with a welcoming porch adorned with black and white chairs. A flag is displayed, and lush greenery surrounds the area. The pool reflects sunlight, complementing the serene atmosphere of the jungle-like backyard.

4.94 out of 5 average rating, 207 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

A guest suite features two double beds with light blankets, positioned beside wooden headboards. Two bedside lamps provide soft lighting, and a small nightstand sits between them. Natural light filters through two windows covered with blinds, illuminating the carpeted floor.

4.96 out of 5 average rating, 246 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 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, 188 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, 206 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 cozy living area is presented, featuring two tan accent chairs and a dark sofa. A wood coffee table is centered on a patterned rug. The kitchen area includes a bar with two brown stools, equipped with modern appliances and tasteful decor.

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

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, 185 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 cozy living area is featured, with a large gray sofa and a comfortable brown armchair. A round wooden table is set nearby, accompanied by black chairs. Bookshelves filled with books line one wall. Natural light enters through shuttered windows, highlighting the old-world brick flooring.

4.95 out of 5 average rating, 516 reviews

Quaint Cottage Refuge in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this cozy eclectic 1930's cottage. Guests will have the entire cottage for their private use. This cottage is filled with unique & eclectic furnishings. Come, stay and enjoy! Spend time on the private screened in porch. Grab a book and relax in the hammock. Central HVAC 1 bed / 1 bath / 1 sofa bed Strict 'No Pet' policy.

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Popular amenities for Southern Pines vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Southern Pines

Camper/RV in Southern Pines

The Airstream's polished exterior reflects the surrounding greenery. Two bicycles are parked nearby, with a small patio area indicated by a few outdoor seating options. Natural pine needles cover the ground, creating a rustic feel in a tranquil outdoor setting.

4.93 out of 5 average rating, 101 reviews

Airstream in the Pines

A small, light blue cottage is surrounded by greenery, set within a fenced area. A bright white door is framed by a simple wooden staircase. The front yard features a gravel pathway and grass, offering a peaceful outdoor setting.

5 out of 5 average rating, 63 reviews

Quiet and Safe neighborhood Studio for 2

A studio layout is presented with a spacious bed featuring soft linens and decorative pillows. A small dining table with stools is positioned near a modern kitchen equipped with stainless steel appliances. Light wood flooring complements the neutral wall color, enhancing the open feel of the space.

5 out of 5 average rating, 32 reviews

The Kensington Cottage

Cottage in Southern Pines

A light and airy bedroom features a spacious bed with soft linens and decorative pillows. A stylish wooden desk with a chair is positioned near a doorway, which leads to an adjoining room. Warm light illuminates the space, enhancing its inviting character.

4.96 out of 5 average rating, 28 reviews

Sage at The Shire 255 - Unit A - Downtown!

A cozy dining area features a rectangular table set for six, surrounded by black chairs. Natural light enters through several windows adorned with blinds. A decorative piece and a potted plant add a touch of warmth, while a sleek refrigerator is visible to the right.

4.95 out of 5 average rating, 19 reviews

Cute cottage close to downtown 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, 98 reviews

New 5 Bedroom Cottage on Pine Needles Golf Course

4.99 out of 5 average rating, 109 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

A spacious bedroom is presented with a king size adjustable bed, dressed in neutral linens. Two bedside tables flank the bed, and a large TV is mounted on the wall opposite. A wood dresser offers additional storage, and a mini fridge is positioned nearby. Natural light enters through multiple windows.