Vacation rentals with outdoor seating in Southern Pines

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Top-rated outdoor seating rentals in Southern Pines

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Guest favorite

Farm stay in Vass

4.95 out of 5 average rating, 129 reviews

Peaceful Horse Farm Retreat

Anahata is a quiet farm retreat dedicated to peace and healing. You’ll stay in our Hunt Box - a spacious studio apartment over the barn with pasture view and fully equipped kitchen. There is space to roam and animals to greet. Please read the full listing prior to booking to ensure that this is the right place for you. For more pics, check out our Insta @anahatafarm. NO third-party bookings - please do not book this room unless you will be the one staying here. NO SMOKING. All are welcome here.

Oct 2 – 9

G$21,792 GYD per night

Guest favorite

Cottage in Southern Pines

4.96 out of 5 average rating, 278 reviews

The Ace Cottage - Tiny-home Feel, Close to golf

Unwind in the privacy of this adorable cottage! 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, bathroom with efficiency shower, a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge with 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!

Dec 25 – Jan 1

G$23,627 GYD per night

Guest favorite

Apartment in Southern Pines

4.97 out of 5 average rating, 176 reviews

Tanglewood Farm B&B Horse Farm- The Fox Den Suite

Weekend Breakfast for Two Included Sat & Sun! Welcome to the Fox Den Suite at Tanglewood Farm B&B! The Fox Den is a private one bedroom (KING) , one bathroom beautifully decorated apartment on our beautiful 10 acre horse farm. Nestled in the heart of North Carolina's beautiful horse county, just minutes from charming downtown Southern Pines, rated as one of America's best small towns to live (Newsmax). Enjoy local breweries, shops, amazing restaurants and over 100 beautiful golf courses.

Aug 27 – Sep 3

G$30,261 GYD per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 142 reviews

Restored 1920s 2BR Cottage w/Bikes-DWTN So Pines

Experience downtown Southern Pines in a stylish fully restored early-1900's cottage. This home is conveniently located 4 blocks (4 min walk) from Broad Street, where you will find all the shopping, restaurants, and bars. The cottage is 5 minute drive to several world-class golf courses (Mid-Pines, Mid-South, Longleaf, Pine Needles, Pinehurst No. 9, Talamore) just to name a few... and only 10 mins away from the Village of Pinehurst and Pinehurst No.2. Cruise like a local on the free bikes!

Mar 22 – 29

G$30,445 GYD per night

Guest favorite

Farm stay in Southern Pines

4.98 out of 5 average rating, 126 reviews

Finally Home Farm Bed and Barn

Bring your horse and your golf clubs! Welcome to Finally Home Farm Bed and Barn! A private 1 bedroom barn converted into a quaint cottage. Located on a peaceful farm just 2 miles from downtown Southern Pines, 1 mile from the back gate of Ft. Bragg and next to Weymouth Woods State Park, Finally Home Farm is the perfect place to explore all the Sandhills has to offer. *We are horse ($40) and dog friendly ($50) pet fee with Pre-Approval. Please include this info in your pre-booking.

Sep 2 – 9

G$23,240 GYD per night

Guest favorite

Guesthouse in Carthage

4.99 out of 5 average rating, 155 reviews

Charming 1 bedroom guesthouse on 4 acres, hot tub

Our guesthouse sits on 4 quiet fenced acres about 100 feet from our home. We are about 15 minutes from Pinehurst. Our large and friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, one queen bed and small fold out sofa. Coffee maker, wine fridge, fire pit with Adirondack chairs for evening glass of wine or to watch the fireflies. Saltwater pool from mid-May to Mid- Sep. Private two-person hot tub. Pet fee.

Mar 27 – Apr 3

G$28,775 GYD per night

Guest favorite

Apartment in Pinehurst

4.98 out of 5 average rating, 217 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. If you want us to stock the refrigerator we will be glad to do so for a small fee.

Oct 12 – 19

G$15,686 GYD per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 146 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!

Aug 30 – Sep 6

G$28,530 GYD per night

Guest favorite

Home in Southern Pines

4.98 out of 5 average rating, 120 reviews

Premier Southern Pines Golf Oasis, Hot Tub Retreat

BEAUTIFUL 1930’S Traditional home with newly remodeled bedrooms,bathrooms and kitchen. Lounge in the Brand New Hot Tub after a round of golf at any of the Nearby World Class Golf Courses. Pine Needles, Long Leaf, Mid Pines, Talamore,to name a few. Perfect for Golf weekends,Wedding guest/Wedding party, friends and family reunion. Romantic getaways or Staycation with plenty of room to unwind, cook ,play and have your own space. Complimentary refreshments when you check in.

Jan 10 – 17

G$70,123 GYD per night

Guest favorite

Guesthouse in Southern Pines

4.97 out of 5 average rating, 213 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.

Jun 27 – Jul 4

G$23,986 GYD per night

Guest favorite

Home in Pinehurst

4.98 out of 5 average rating, 663 reviews

The Knotty But Nice Treehouse of Pinehurst

Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.

Oct 16 – 23

G$36,625 GYD per night

Guest favorite

Condo in Pinehurst

4.99 out of 5 average rating, 103 reviews

To The Green On #17 - Studio w/ GREAT Golf Views!

PERFECT LOCATION - only a 5 minute walk to the Pinehurst Golf Clubhouse! "To The Green On #17" is a second-story studio condo perfectly located on hole #17 of Pinehurst No. 3 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy yet luxurious finishes combined with an excellent location make this studio condo perfect for a weekend golf getaway or an extended stay!

Aug 29 – Sep 5

G$26,021 GYD per night