Holiday rentals with a fireplace in Southern Pines

Guest suite in Downtown Southern Pines

4.93 out of 5 average rating, 68 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.

4.99 out of 5 average rating, 176 reviews

Home in Pinebluff

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay and Play Retreat! We are centrally located just 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 over 20 beautiful golf courses including Legacy Golf Links and a wide variety of dining options within 11 miles of this completely renovated home that has been created specifically for your comfort, relaxation & enjoyment.

4.9 out of 5 average rating, 119 reviews

The Chatham House

The Chatham House is a privately-owned 3 bedroom/2 bath vacation home located in the famed Pinehurst #6 - just minutes away from the Village of Pinehurst shops and restaurants. This home-away-from-home features everything you need for a relaxing/fun vacation. Whether you have come to play some of the best golf courses in the world or have come for a fun family vacation, the Chatham House is your place to stay! Also great for Doctors and Nurses as First Health hospital is just minutes away.

4.98 out of 5 average rating, 113 reviews

Villa in Pinehurst

A Cozy Retreat on No. 5

Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.

4.92 out of 5 average rating, 171 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! 10 minutes to Pinehurst resort, great patio and large fenced yard shared with the lower unit (pet friendly). This upper unit has a full kitchen, King bedroom with en suite bathroom, two Queen bedrooms, a second bath, an electric fireplace in the living room, 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!

5 out of 5 average rating, 76 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!

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!

4.99 out of 5 average rating, 108 reviews

Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst

Come relax at the luxurious Lucky Lie! This beautifully renovated studio condo is located just off the beaten path on Pinehurst No. 3, but still perfectly situated for an easy approach into downtown Pinehurst and the surrounding Sandhills. Unwind after your rounds on the porch over looking No. 3, 16th fairway, relax in front of the electric fireplace, or knock out some work in the dedicated workspace, the Lucky Lie has what you're looking for!

Apartment in Downtown Southern Pines

4.87 out of 5 average rating, 156 reviews

Belleview on Bennett, Heart of Downtown So Pines!

This cozy second-story apartment is just a short, easy walk to all the shopping, fine dining, cafes, restaurants, nightlife, and entertainment along Broad Street in Downtown Southern Pines. Enjoy the convenience of being right in the center of it all! Optional concierge services are available, including daily housekeeping, grocery delivery, pantry stocking, floral arrangements, and more. Pinehurst #2 is approximately 6.6 miles away.

4.98 out of 5 average rating, 110 reviews

Cozy Pinehurst Retreat w/ Putting Green

Enjoy your Pinehurst stay in the family-friendly neighborhood of Village acres. The area is surrounded by The Greenway pedestrian and bicycling trail. The house is situated within 2 miles of downtown Pinehurst, Camelot Park, and Rassie Wicker Park, and is a short drive away from any of the many wonderful golf courses that Pinehurst has to offer. The house was recently remodeled and is well furnished, to make for a comfortable stay.

4.95 out of 5 average rating, 277 reviews

Guesthouse 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.

4.95 out of 5 average rating, 153 reviews

Highland Hideaway/Pool & Fire Pit/$0 Cleaning Fee

Nestled in a peaceful neighborhood just a few miles from downtown Southern Pines and multiple world-renowned golf courses ⛳️ . A 3-bedroom / 2.5-bathroom home with a bonus room. Spacious open porches overlook an inground pool, perfect for those hot summer days, and a fire pit, perfect for relaxing during the evenings. This home is also a short drive to Fort Liberty and surrounding hospitals.

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Holiday House Rentals with a fireplace

5 out of 5 average rating, 79 reviews

This is it! | Pool | Golf | Convenient to Town

DelosRating, 5 stars2 weeks ago

Great location, beautiful home, plenty of space, clean, everything in great shape. Hosts were communicative and responsive. Pool was nice, ping pong table was fun to use. Would stay again.

5 out of 5 average rating, 28 reviews

The Estate - Across from SP Golf Club

IkaisherronRating, 5 stars1 month ago

Will recommend to others that are in the area. This property was nice, cozy and tucked away. Close traveling distance to needed stores amd eateries.

4.99 out of 5 average rating, 94 reviews

Perfect golf getaway - quick drive to all courses

AnneRating, 5 stars1 week ago

Beautiful home with an equally beautiful setting. The kitchen was well equipped. We spent an amazing time with family. There was plenty of room for all. Very comfortable. Hosts were great as they checked with us often to make sure all was well.

4.95 out of 5 average rating, 157 reviews

⛳️19th Hole🍸. Sleeps 10, Pool Table🎱 and Fire Pit

TerryRating, 5 stars2 weeks ago

We loved the house and the location. Super clean and spacious. We could not have asked for it to be any better. Wonderful time for our family!!!

Home in Downtown Southern Pines

5 out of 5 average rating, 23 reviews

The Pinecone Cottage - a Southern Pines escape

PatriciaRating, 5 stars2 months ago

Great location for our reason coming to Pinehurst. Rooms were nice. Only issue was the pull out couch. The mattress is thin and very uncomfortable. Otherwise, no complaints!

4.94 out of 5 average rating, 18 reviews

Timeless Tudor - 4 bedrooms and 2.5 baths!

MyrtriceRating, 5 stars1 month ago

There were eight of us and the house had everything we needed plus great style, which we also appreciated!

Home in Downtown Southern Pines

5 out of 5 average rating, 48 reviews

Newly remodeled Downtown Cottage-walking distance

RanieRating, 5 stars1 month ago

Great location for walking to shops and restaurants in downtown Southern Pines. House was perfect for our girls weekend. Beds were very comfortable and each room had their own bathroom. We enjoyed the back porch in the evenings before going out to dinner. Definitely recommend over a hotel for your next visit to SP! We had a super minor issue and owner on top of immediately!

5 out of 5 average rating, 89 reviews

Comfy Pinehurst Home near Golf w/ Ping-pong

JosephRating, 5 stars2 months ago

Great house! Close to everything golf related!

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Apartment rentals with a fireplace

Superhost

Apartment in Fayetteville

4.79 out of 5 average rating, 14 reviews

The All American Suite

RachelRating, 5 stars2 weeks ago

My daughter grandson and I really enjoyed our stay. My bed was super comfortable and when I forgot to reserve the playpen and high chair for my 1yr old grandson Heather was kind enough to go out of her way to bring them over. Next time I visit my daughter and son in law I would definitely stay here again.

Superhost

Apartment in Pinehurst

Pinehurst Tee Time Retreat w/ Community Pool

LarissaRating, 5 stars4 months ago

I had a wonderful stay at this condo in Pinehurst! It's just 2 miles from the village, making it easy to explore the shops and restaurants. I even braved the cold and walked to the Pinehurst Track Restaurant, which was a nice bonus. The pool would be amazing in warmer weather but walking down to the lake was equally relaxing. The condo was comfortable, clean, and well-decorated, offering everything I needed. The hosts were super friendly and accommodating, especially with my last-minute booking. Highly recommend this spot for anyone visiting Pinehurst—great location, cozy atmosphere, and fantastic hosts!

5 out of 5 average rating, 72 reviews

Apartment in Pinehurst

Captain’s Choice

MarkRating, 5 stars2 weeks ago

This was our second stay at Captain's Choice. It's a very cozy and comfortable condo, with practically everything you'll need for any length of stay. Barbara is a great host and excellent communicator. She makes you feel honored to have you and is very welcoming. Five stars for sure!