Holiday rentals in Southern Pines

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Top-rated holiday rentals in Southern Pines

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

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Top guest favourite
A soothing hot tub is illuminated by soft blue lights, creating a calming ambiance. The surrounding area features a modern privacy screen, subtly highlighted by exterior lighting, enhancing the serene nighttime setting.
Home in Pinebluff
5 out of 5 average rating, 236 reviews

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay and Play Retreat! We’re centrally located minutes away from some of the areas greatest attractions such as Pinehurst No. 2 (8 Miles), Rockingham Dragway (14 miles), Carolina Horse Park (10 miles), and Fort Bragg (16 miles) . We're also surrounded by numerous golf courses including Pinehurst & Legacy Golf Links. A wide variety of dining options are within 11 miles of this completely renovated home that has been created specifically for your comfort, relaxation & enjoyment!

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

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
Apartment in Pinehurst
4.95 out of 5 average rating, 272 reviews

- Guest Favorite - Peaceful Pinehurst Golf Condo

Welcome! This clean, cozy ground-floor golf-front Pinehurst condo is ideal for golf trips, weekend excursions, longer visits, even staycations. Enjoy a well-stocked kitchen, comfortable furnishings, and a screened porch with peaceful fairway views - perfect for morning coffee or evening wine! Super close to the Village, prime dining and shops, the Fair Barn, harness track and Pinehurst Resort; just 10–15 minutes to Southern Pines and Aberdeen. Quiet, walkable and a perennial guest favorite!

Top 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, 406 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!

Top guest favourite
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.
Guest house in Southern Pines
5 out of 5 average rating, 101 reviews

Quiet and Safe neighborhood Studio for 2

Enjoy a peaceful stay in this fully furnished studio for two, located in a quiet Southern Pines neighborhood. Separate unit behind the main home, 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

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 Southern Pines
4.98 out of 5 average rating, 112 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.

Top guest favourite
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.
Cottage in Southern Pines
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!

Guest favourite
Home in Southern Pines
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.

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, 113 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
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.
Home in Southern Pines
4.96 out of 5 average rating, 223 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
An open living space features brick flooring, a cozy seating area with a sofa and armchair, and a wall of bookshelves filled with books. A television is mounted on the wall, and warm light is provided by lamps. A dining table and kitchen island are present, enhancing functionality.
Home in Southern Pines
4.99 out of 5 average rating, 144 reviews

Charming Retreat in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. This charming retreat is unique, eclectic and super cozy! Stay, enjoy and relax in the confines of which used to be a garage. This space features all brick floors, lots of windows with plantation shutters, books, a comfy bed, walk in tiled shower, kitchen and quite distinctive décor. Peruse the large selection of books and enjoy some reading during your stay.

Top guest favourite
Home in Southern Pines
4.94 out of 5 average rating, 103 reviews

Historic Hidden Gem - Downtown Southern Pines!

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 holiday rentals

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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 townhouse rentals in Southern Pines?

    Southern Pines has more than 20 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Southern Pines with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do townhouse rentals in Southern Pines have air conditioning?

    Absolutely! We offer over 20 townhouse rentals with air conditioning in Southern Pines. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Southern Pines have wifi?

    Absolutely! We offer over 10 villa 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 holiday rentals in Southern Pines

  • Total holiday rentals

    Explore 380 holiday rentals in Southern Pines

  • Nightly prices starting at

    Southern Pines holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 16,690 verified reviews to help you choose

  • Family-friendly holiday rentals

    270 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    380 of Southern Pines holiday 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!