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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Guest favourite
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.
Cottage in Southern Pines
4.96 out of 5 average rating, 388 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!

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, 116 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.

Top guest favourite
A quaint exterior of a bungalow is shown, framed by tall trees and lush greenery. A trellis is visible, adding charm to the entrance. Natural light filters through the scene, creating a warm ambiance in the garden area.
Guest suite in Downtown Southern Pines
4.92 out of 5 average rating, 501 reviews

Cozy Studio 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 small, yet quaint & cozy self contained studio/efficiency which is attached to a 1930's bungalow. Just steps to our idyllic downtown. (Literally 1 block). Guests will have the entire studio for their private use. (bed, bath, kitchenette) Central heating and air with thermostat 1 bed / 1 bath. Private entrance. Street parking. 'Strict' No Smoking Policy

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, 228 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
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.
Guesthouse in Southern Pines
4.98 out of 5 average rating, 259 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.

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
4.92 out of 5 average rating, 317 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
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.
Guest suite in Southern Pines
4.96 out of 5 average rating, 255 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.

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, 104 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 comfortable sitting area includes a gray sectional sofa paired with a round coffee table, adorned with small decorative items. Natural light enters through patio doors leading to a private garden. A queen bed with a light coverlet is positioned nearby, enhancing the cozy ambience.
Apartment in Pinehurst
4.98 out of 5 average rating, 301 reviews

Pinehurst #6 Garden Getaway

A warm welcome to our cozy 1 BR/1 BA apartment in the Pinehurst #6 community. It has a queen bed and a queen sofa bed if needed. We are close to the Village of Pinehurst and dozens of amazing Golf courses. We are less than 2 miles from First Health Moore Regional Hospital. Nearby you can enjoy shopping, dining, 4 local breweries and a winery. We also offer housekeeping for only $ 10 a day. PLEASE LET ME KNOW, when booking IF YOU NEED THE SECOND BED.

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, 106 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.

Top guest favourite
A modern vanity area features a large mirror framed by geometric tiles in a soothing blue hue. A cushioned stool with a gold frame complements the sleek, dark cabinetry. Soft lighting enhances the stylish setup, offering an inviting space for personal grooming.
Condo in Pinehurst
4.96 out of 5 average rating, 157 reviews

The Suite Spot

This centrally located suite is the perfect spot for your next visit to Pinehurst. Come and enjoy the views from the back covered porch, book a tee time at one of Pinehurst’s world renowned golf courses, soak up some North Carolinian vitamin D and then take a dip in the pool, or simply stay indoors and let The Suite Spot be your sweet respite from the world.

Top guest favourite
A cozy cabin is set against a backdrop of trees, featuring a gravel driveway and a fenced yard. A wooden deck with benches is visible at the front, inviting relaxation. The exterior is clad in gray with a green door, blending harmoniously with the natural surroundings.
Cabin in Southern Pines
4.95 out of 5 average rating, 320 reviews

Cozy Cabin in Southern Pines

A wonderfully cozy cabin with its own driveway and gated area. Enjoy a yard of your own on a quiet street. Close to downtown Southern Pines and Aberdeen. Big front porch and rear porch with complete privacy. There are miles of beautiful nature trails nearby including Weymouth Woods and the All American Trail.

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 240 vacation rentals in Talamore, over 50 vacation rentals in Highland Trails, and over 370 vacation rentals in Downtown Southern Pines.

  • 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 30 vacation homes with pools in Southern Pines, available on Airbnb. Make a splash and soak up the sun in style!

  • Do guesthouse rentals in Southern Pines have wifi?

    Absolutely! We offer over 10 guesthouse 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 60 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.

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

    Southern Pines has more than 200 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do villa rentals in Southern Pines have air conditioning?

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

  • 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 $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about vacation rentals in Southern Pines

  • Total vacation rentals

    Explore 370 vacation rentals in Southern Pines

  • Nightly prices starting at

    Southern Pines vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 15,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    260 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    370 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!