Vacation rentals in Southern Pines

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Top-rated vacation rentals in Southern Pines

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
Guest suite in Downtown Southern Pines
4.96 out of 5 average rating, 112 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.

Top guest favourite
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.
Apartment in Southern Pines
4.96 out of 5 average rating, 107 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

Guest favourite
Home in Southern Pines
4.93 out of 5 average rating, 208 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! 10min to Pinehurst resort, 17min to Carolina Horse Park, large deck and fenced yard shared with the lower unit (pet friendly). This single-level upper unit has a full kitchen, King bedroom with en suite bathroom, two Queen bedrooms, a second bath, an electric fireplace, 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!

Top guest favourite
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.
Home in Southern Pines
5 out of 5 average rating, 127 reviews

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.

Top guest favourite
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.
Home in Southern Pines
4.96 out of 5 average rating, 250 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!

Top guest favourite
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.
Home in Downtown Southern Pines
4.98 out of 5 average rating, 110 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
4.9 out of 5 average rating, 328 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.

Top guest favourite
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.
Home in Southern Pines
5 out of 5 average rating, 112 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!

Top guest favourite
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.
Home in Downtown Southern Pines
4.96 out of 5 average rating, 220 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.

Top guest favourite
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.
Home in Southern Pines
4.97 out of 5 average rating, 225 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!

Top guest favourite
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.
Bungalow in Downtown Southern Pines
4.97 out of 5 average rating, 397 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.

Top guest favourite
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.
Home in Southern Pines
4.97 out of 5 average rating, 118 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.

Popular amenities for Southern Pines vacation rentals

When is the best time to visit Southern Pines?

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Frequently Asked Questions

  • Where should I stay in Southern Pines?

    Make yourself at home in Southern Pines by choosing from our most frequently booked neighborhoods. We have over 370 vacation rentals in Downtown Southern Pines, over 60 vacation rentals in Highland Trails, and over 230 vacation rentals in Talamore.

  • Are there pet-friendly vacation rentals in Southern Pines?

    Four-legged friends are welcome in Southern Pines. Choose from more than 150 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Southern Pines?

    Yes! Work meets play with ease at over 210 vacation rentals in Southern Pines featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Southern Pines vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Southern Pines, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Southern Pines?

    Southern Pines has more than 270 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in townhouse rentals in Southern Pines?

    Experience the best of Southern Pines with our townhouse rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do boutique hotel rentals in Southern Pines have air conditioning?

    Absolutely! We offer over 10 boutique hotel rentals with air conditioning in Southern Pines. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Southern Pines have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Southern Pines. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Southern Pines have a bbq area?

    Absolutely! We offer over 50 house rentals with a bbq area in Southern Pines. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Southern Pines have a gym?

    Absolutely! We offer over 30 house rentals with a gym in Southern Pines. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Southern Pines

  • Total vacation rentals

    Explore 380 vacation rentals in Southern Pines

  • Nightly prices starting at

    Southern Pines vacation rentals start at $54 CAD per night before taxes and fees

  • Verified guest reviews

    Over 16,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    270 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    380 of Southern Pines vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Southern Pines rentals

  • 4.9 Average rating

    Southern Pines stays are highly rated by guests—averaging 4.9 out of 5!