Holiday rentals in Southern Pines

Cottage in Southern Pines

4.96 out of 5 average rating, 355 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!

5 out of 5 average rating, 28 reviews

The Kensington Cottage

Relax and unwind in our newly-renovated cottage, just a short walk from downtown Southern Pines! Spend the day admiring the beauty of the local trails and Sandhill Horticultural Gardens, or explore the quaint "SoPi" shops and Sunrise Theater. Only a ten minute drive to Pinehurst, the area boasts some of the nation's best golfing and a fabulous restaurant scene. The cottage features a new Nectar queen mattress, fast WiFi, an oversized shower, a modern kitchen, and a private yard with fire pit.

4.94 out of 5 average rating, 52 reviews

Bungalow at the Lake

Private guesthouse bungalow with lake access, on the property. 7 minutes from downtown Southern Pines. 15 minutes from Pinehurst Country Club. Apartment over garage with separate, private entrance and lots of parking space! Kitchenette with fridge and Keurig coffee maker, King size adjustable bed, large TV, private bathroom, and WiFi! Back yard amenities include fire pit, private dock, deck space, and lake access + kayak! Hosts on site and available for any issues during your stay.

4.94 out of 5 average rating, 104 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!

4.98 out of 5 average rating, 241 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.

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

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

4.97 out of 5 average rating, 182 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!

4.96 out of 5 average rating, 203 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.

4.97 out of 5 average rating, 178 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!

4.95 out of 5 average rating, 506 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.

4.95 out of 5 average rating, 277 reviews

Guest house in Carthage

Carthage Country Guesthouse

This is a peaceful area with time to just slow down a little. Looking for a little peace & quiet? I have the place for you. Very cute Guesthouse nestled deep in the country area of Carthage. It's like taking a few steps back in time when life was simple. We are located within minutes to Pinehurst, Seven Lakes, Cameron, Pottery Highway and downtown Carthage. A very quiet area with nothing but the sounds of Mother Nature.

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Popular amenities for Southern Pines holiday rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Southern Pines

4.91 out of 5 average rating, 65 reviews

Guest house in Pinehurst

Sunny Pines Hideaway

JohnRating, 5 stars3 weeks ago

One of the best Airbnb's I've seen. Charming, quirky, luxurious, well equipped. Like a fantasy cottage retreat. Huge wraparound porch looking down on private wooded back yard for sitting and talking in the evening. Every type of glass, cup, pan and plate. Coffee and tea supplied. Host was super-chill, guiding us where to park, how to get in. The cottage is outfitted with nice design touches, rustic style, but fine finishes, furnishings and materials to delight guests. Huge shower. Even a basket full of new sealed toothbrushes! Host really cares about guests convenience and enjoyment. A cut above 90% of the places I've rented. Bravo!

Farm stay in Southern Pines

4.97 out of 5 average rating, 75 reviews

The Horse & Hound at Tanglewood Farm B&B

ErikaRating, 5 stars3 months ago

We had a great stay for my husband’s birthday. The hosts were incredibly kind, responsive, and the farm is lovely. I also can’t speak highly enough about the breakfast option. You’ll love it!

5 out of 5 average rating, 9 reviews

2 Master King Suites • Fire Pit • Games I Location

AnthonyRating, 5 stars1 week ago

The home was perfect for our stay! It was close proximity to all of the golf courses we were going to, which made it convenient. Laila was very responsive and helpful with additional info on go-to restaurants.

4.9 out of 5 average rating, 31 reviews

Apartment in Pinehurst

The Mulligan Manor - 1BR/1BA Condo in Pinehurst

MaryRating, 5 stars4 days ago

Paul and Eki were great and responsive hosts. Their home was never more than 10 minutes from anything we wanted to do in Pinehurst and Southern Pines. The place was super clean, adorable and was perfect for our three day getaway. The king bed was very comfortable and had plug access for electronics. The home is very quiet. No noise from upstairs neighbors and no noise from AC or water heaters. The AC was easy to control. The shower had good water pressure and towels were supplied. We loved having access to a Keurig in the morning for our coffee. Harris Teeter and Lowe's grocery stores were right nearby. We golfed each day and had great dinners each night. We especially loved Elliott's on Linden. Highly recommend Paul and Eki's place for a few days away or longer. While we didn't use it, the kitchen was well equipped and even included an InstantPot. And what a great price for all of that! Very pleased with the value.

4.95 out of 5 average rating, 58 reviews

Lavender Bliss Retreat-65”TV- Private Patio

SiobhanRating, 5 stars3 weeks ago

Our stay was wonderful! Everything was just as described. The bed is very comfortable, plenty of hot water, very easy check out and great size for my daughter and myself. We were in town for a horse show at CHP and it was convenient to get to. Host was very nice making sure we had everything we needed. Hope to stay again in the future!

Holiday home in Southern Pines

5 out of 5 average rating, 31 reviews

Horse and Golf Heaven - 2 BR Apt on Horse Farm

AndrewRating, 5 stars2 months ago

This was our second time staying here! The apartment is clean, spacious and stocked with everything you could need. We love sitting outside and enjoying the view of the pastures. If you aren’t in the mood to cook there are great restaurants and breweries 10 minutes away. We also brought two horses that stayed on the farm in a spacious safe pasture with run in shed. The trails are right off the property and go for miles. The dogs love the dog door and the fenced yard keeps them safe. Family joined us for a few days to take advantage of all of the golf course options. Carrie and Bill are fantastic hosts that go out of their way to help make your stay amazing. We highly recommend staying here - it really is horse and golf heaven.

4.84 out of 5 average rating, 37 reviews

Dive Into The Pines-walk DT, new pool, fenced yard

MissyRating, 5 stars2 months ago

My best friend and I came to Kaitlyns AirBnB for a Girl's Trip Weekend. The house was wonderful and the beds were comfy. The layout of the house gave my friend and I our own areas for privacy but also had a very welcoming living room and sun room for catching up and drinking coffee and tea. The neighborhood was quiet and everyone we came into contact with was super nice and helpful. If you want a place to unwind, relax, and reconnect with family or friends this is definitely the place for you!