Vacation rentals in Southern Pines

A dining area is viewed, featuring a wooden table surrounded by black chairs. A light fixture hangs above the table, while a sliding glass door allows natural light to fill the space. The kitchen area is visible, showcasing white cabinetry and modern fixtures.

4.82 out of 5 average rating, 299 reviews

The Perfect Lie in Pinehurst!

RobertRating, 5 stars3 weeks ago

We have stayed at Barbra's place several times and always find it great. Barbra is very responsive and the place is clean and well located for our golf tournaments. Plenty of room to stretch out in a couple of large recliner chairs. Nice location on a golf course. Everything worked fine and the pantry was well stocked with incidentals. We have stayed in the area multiple times and this is our choice to return to each year.

A warmly colored dining area is highlighted by a large round table surrounded by eight black leather chairs. Natural light enters through tall arched windows, complementing the rich orange walls and decorative white wainscoting. A classic chandelier hangs above, adding elegance.

4.98 out of 5 average rating, 126 reviews

The Ross Retreat - In Pinehurst

BrendanRating, 5 stars3 weeks ago

The guys planned a golf trip and found a spot that checked all the boxes. The house is big enough so everyone had enough space and the house included everything we needed like towels, bath essentials and streaming to watch March Madness. The hot tub was a great perk after a long round of golf and the patio was a great hang out spot. The house is only a couple minute drive to the Village and central to most courses. Our favorite course was Tobacco Road and would definitely recommend that challenging yet highly entertaining course.

A decorative glass pumpkin sits atop a white pedestal. The pumpkin is a vibrant blue color with intricate patterns reflecting light, set against a backdrop of greenery visible through a nearby window.

4.95 out of 5 average rating, 112 reviews

"Perched in Pinehurst"

SandeepRating, 5 stars8 months ago

What a nice cozy place right on hole 1 of pinehurst #5. We watched golfers go by and we're loving the hustle bustle of any golf tournaments played at the course. The place is minutes away from the pinehurst clubhouse with 18 hole putting area and the famous cradle 9 hole course. We came for golf and enjoyed every bit of our stay but would have loved the place otherwise as well. Things were convenient around

The exterior view features a modern home with large windows offering a glimpse of the interior. A patio with a table and chairs is set on concrete, surrounded by a neatly maintained yard and a white picket fence, creating a welcoming outdoor space.

4.97 out of 5 average rating, 34 reviews

⛳ Golf & Family Bungalow - Convenient to Village

AmandaRating, 5 stars2 weeks ago

The house was great for our girls’ trip! The house was well stocked, clean, easy to find all the info we needed (like check in, Wi-Fi info, check out) and a great location to the spa and downtown pinehurst! We had plenty of space in the house.

4.92 out of 5 average rating, 197 reviews

A wooden deck offers a view of the surrounding greenery and the calm waters of the lake. Trees and bushes frame the scene, with a rock outcrop visible across the water. Natural light illuminates the outdoor area, enhancing the serene setting.

Cottage in Pinebluff

Lakeside Cottage nestled near Pinehurst and CHP

SharonRating, 5 stars6 days ago

My second stay here , I am almost 70 years old but hope to come again this fall . Beautiful & peaceful . If some of the brush & small trees were down we could get better view of the lake . Caught brim & bass , enjoyed ducks & turtles .

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What guests are saying

NEW BUILD Golf Cottage-Perfect for Couples/Family

5 out of 5 average rating, 47 reviews3 days ago

We loved our stay at this cute cottage and will definitely be back next time we’re in town! The cottage was spotless and very cozy — we had everything we needed for our weekend trip. The location is perfect, close to many great restaurants and things to do, but also tucked away and nice quiet street. Amanda was super helpful and responsive as well.

Home in Pinehurst

What guests are saying

Welcome to 19th Tee. Sirene Golfviews for 4.

4.89 out of 5 average rating, 73 reviews1 month ago

We had a fantastic stay at this location! The view was a perfect backdrop. It’s also ideally situated, just a short walk away from all the shopping and dining options downtown, making it incredibly convenient. Highly recommend for anyone looking to stay in Pinehurst.

Condo in Pinehurst

What guests are saying

Luxury Vacation Home "Lakeside in Pinehurst"

4.98 out of 5 average rating, 51 reviews1 month ago

This was our second stay at this beautiful house and we loved every minute of it. We caught lots of fish off the dock, ate family dinners on the deck, went for long walks around the neighborhood, played the Cradle while enjoying this meticulously clean and perfectly appointed house. Sondra and Jody were very responsive and very helpful!! We can’t wait for our next stay!!!

Vacation home in Pinehurst

What guests are saying

cheerful 4 bedroom cottage in perfect location

5 out of 5 average rating, 21 reviews1 week ago

Lisa’s accommodations were beyond expectations. The home was adorable and very spacious. Just wish we had more time to spend to here! Lisa was super quick to respond and very helpful every step of the process. We would definitely love to stay here again in the future!

Home in Pinehurst

What guests are saying

Escape to Twin Oak Acres

5 out of 5 average rating, 46 reviews1 month ago

The pictures don't hold a candle to how nice this place truly is! It is well equipped in all spaces. You immediately feel at home. We settled in quickly and thoroughly enjoyed the peaceful surroundings after our long drive. This home was an excellent location for us to do our exploring of the surrounding areas. I was pleased to find a Keurig and a coffee pot to use for our stay. We were able to enjoy having my husband's family over for dinner twice with space to accommodate us all, letting the kiddos entertain themselves on the swings and with plenty of space to explore. We will definitely be looking this place up first for our next visit!

Home in Vass

What guests are saying

Carolyn's Pinehurst Abode

5 out of 5 average rating, 8 reviews4 weeks ago

I can’t say enough good things about Carolyn’s place in Pinehurst. First, she let us check in at the last minute around 10pm when we were desperate to find a place to stay. The house is located in an adorable, quiet, walkable neighborhood. It’s 0.85 from the PineScone Cafe. We walked to get coffee multiple mornings. It’s also 2.4 miles from Pinehurst Village and the historic Pinehurst Golf Resort. We spent several Saturdays walking to the village, getting breakfast / coffee, checking out the beautiful homes, shopping, and sitting at the Pinehurst resort around their beautiful gas fire pits. We also went to the spa at the resort one day. There are plentiful restaurant choices in Pinehurst / Southern Pines to explore. The gas grill in the backyard was wonderful to have at the home. We made steaks and grilled chicken multiple nights. The large walk in shower in the big bathroom was great for my tall husband. We definitely recommend Carolyn’s place and would stay there again!

Home in Pinehurst

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Popular amenities for Southern Pines vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Southern Pines's top sights

Betsy's Crepes69 locals recommend

Ironwood Cafe54 locals recommend

Weymouth Woods - Sandhills Nature Preserve43 locals recommend

Southern Pines Growler Company41 locals recommend

Chapman's Food and Spirits39 locals recommend

Ashten's37 locals recommend

Boutique hotels in Southern Pines

A lounge area is shown with elegant chandeliers illuminating the space. Dark wood accents frame the room, featuring seating arrangements with comfortable chairs and a tufted sofa. A large painting adorns the wall, adding a classic touch, while ambient light filters through large windows.

4.4 out of 5 average rating, 5 reviews

The Jefferson Inn • Rm. 5 | Deluxe Guest Room

LindaRating, 5 stars11 months ago

My go to place to stay in Southern Lines. They always take great care of us

A tree-lined street presents a charming view of brick buildings and boutique storefronts. Lush greenery from nearby planters complements the sidewalk, while parked cars line one side, providing a sense of community and activity in this inviting urban setting.

4.8 out of 5 average rating, 5 reviews

The Jefferson Inn Rm. 4 | Deluxe Guest Room

Katherine SueRating, 5 stars10 months ago

Super cute, hotel like place to stay in a fun downtown area! Great place to stay.

The lounge area features plush seating arrangements with tufted leather sofas and elegant armchairs. Crystal chandeliers illuminate the space, where rich wooden details and dark walls provide a sophisticated atmosphere. A framed artwork depicting a serene equestrian scene adds a touch of character to the room.

5 out of 5 average rating, 3 reviews

The Jefferson Inn Rm. 7 | Deluxe Guest Room

BonnieRating, 5 stars10 months ago

Room was exactly as pictured. Huge bathroom. So great. Right downtown Southern Pines right over a restaurant. We had a blast.

The lounge area features elegant chandeliers hanging from dark wood ceilings. Richly toned walls are complemented by comfortable seating arrangements, including tufted armchairs and a plush couch. Light from large windows illuminates the space, creating a sophisticated atmosphere perfect for relaxation.

5 out of 5 average rating, 9 reviews

The Jefferson Inn • Rm. 13 | Standard Guest Room

BrookeRating, 5 stars5 months ago

Loved the accommodations and great location!

The lounge area features a rich color palette with dark wood accents and plush seating. Elegant chandeliers provide ambient lighting, while a framed painting hangs on the wall. Leather couches and armchairs are arranged around a coffee table, inviting relaxation and conversation.

5 out of 5 average rating, 3 reviews

The Jefferson Inn • Rm. 9 | Standard Suite

RaymondRating, 5 stars7 months ago

The Jefferson Inn was an amazing experience—from the comfy furniture, relaxing rainfall shower, to the awesome entertainment and drinks on the patio and lounge. It was walkable to all broad street dining, drinking, and shopping and I would definitely stay again!

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Other great vacation rentals in Southern Pines

4.94 out of 5 average rating, 53 reviews

An outdoor deck is furnished with four lightweight chairs surrounding a round table. The natural wood surface contrasts with the greenery of the surrounding trees and the clear blue sky, creating a serene spot for relaxation.

Home in Southern Pines

New Pines Retreat -Brand new home!

DwayneRating, 5 stars4 weeks ago

The only problem was the lock stuck. We arrived at 2 am and didn't get in the house until 3 am. Had to wake Lucy at 3 in the morning. She had a backup key, but a different code. Later found out that if we had physically pushed the door while using code it would have worked. Other than that, great place.

A bright hallway showcases a carpeted staircase leading to the upper level. Natural light filters through the open door at the end, highlighting a small seating area with greenery. The walls feature simple decor and a round clock is mounted near the entrance.

4.91 out of 5 average rating, 23 reviews

Cozy 2 bedroom condo near Pinehurst golf courses

RodRating, 5 stars8 months ago

Lilia was an amazing host. We've stayed in 4 or 5 condos in Pinehurst and Lilia's was by far the most spacious and homey of all. It's a 2 story with 2 bedrooms upstairs, which we've never seen before and really appreciated. Most Pinehurst condos are on a single floor, so someone else is either staying above or below you, and any upstairs-only condo requires lugging sets of golf clubs up and down the stairs daily, which can be a hassle and annoying to neighbors. Lilia's condo has 2 assigned parking spots in front so you can drive up and move clubs, luggage, groceries, etc. inside easily. My 76 year old mother stayed with us. Walking up the stairs not a problem for her. The kitchen is huge for a Phurst condo. Living area was nice and comfortable. The patio is sail shade covered, turf floored, private and quiet. I snuck in a couple of glorious naps out there. The condo residents are a mixture of owners who live year round. as well as other AirBnb's. We never noticed neighbors while indoor

4.95 out of 5 average rating, 38 reviews

A cozy fire pit area is surrounded by five gray chairs arranged in a circular pattern. The fire pit is constructed from stone, with a warm flame flickering at the center. Soft lights illuminate the surrounding gravel and grassy area, creating an inviting ambiance.

Home in Southern Pines

The Oakmont Cottage

CaitlinRating, 5 stars1 month ago

Had a great weekend at Troy’s place while in town for a competition at the Carolina horse park! Only a 20 minute drive and very close to lots of great restaurants

A modern home is set amidst tall trees, featuring a white facade with dark trim. A welcoming front porch is visible, adorned with potted plants. The well-maintained lawn is complemented by a gravel path leading to the entrance, highlighting the peaceful surroundings.

4.97 out of 5 average rating, 77 reviews

Farmhouse at No. 6

BrianRating, 5 stars3 months ago

Great place to stay if you’re in town for golf. The owners were very responsive to any questions and the place was spacious, clean and just what we needed. Can’t wait to go back.

A private outdoor space is depicted, featuring a hot tub with a protective cover. Two white lounge chairs and a small table are positioned nearby, surrounded by natural foliage. The area is paved with brick and offers a serene atmosphere, complemented by the greenery in the background.

4.94 out of 5 average rating, 50 reviews

Pinehurst - Fantastic Location!

BrookRating, 5 stars3 weeks ago

The house was perfect for 8 golfers. Patio with hot tub was a great place to relax after a day of golfing.

5 out of 5 average rating, 87 reviews

A spacious living room features a cozy seating arrangement with light brown leather sofas and two dark armchairs. A flat-screen television is mounted above a decorative fireplace. Natural light streams in through sliding glass doors, leading to an outdoor deck with additional seating options.

Home in Southern Pines

New 5 Bedroom Cottage on Pine Needles Golf Course

WarrenRating, 5 stars2 weeks ago

Perfectly located with modern amenities. Clean throughout. Jason was readily available and communicated clearly. Ideal home base for the area. Would stay there again with zero hesitation.

An outdoor patio area features a sleek black bar with high stools, overlooking lush greenery. A putting green is included, enhancing the space for leisure activities. Natural light floods in through expansive glass sliding doors, connecting the patio to the interior living area.

4.9 out of 5 average rating, 63 reviews

Pinehurst Golf, Weddings, Seminars with Hallmark A

TimRating, 5 stars2 weeks ago

Tim's place was welcoming and he was a responsive, available host. Check-in was smooth and easy. Check-in tips: If arriving at night, the lighting is low and condo unit numbers unobtrusive, so recommend having a good lighting source. Also, the condos are numbered sequentially up one side of the drive-way and down the opposite side v odds or evens all on one side as is typical in residential US. Tim's is toward the end on the left. Just a tip. Walking to town. Google will have you walking 1.5 miles back out of the development. But, if you go left out of the condo, walk to the end of the driveway, cross the green/fairway, you'll be on a main road that takes you directly to town, cutting a mile off the Google directions. Enjoy.