Vacation rentals with a patio in Southern Pines

The Cottage on Midland

Keep it simple at this peaceful, centrally-located single family home. The Cottage on Midland is a charming retreat nestled among tall pine trees, offering a serene escape just minutes from downtown and world famous golf courses. This cozy home exudes warmth and comfort, featuring inviting living spaces, modern amenities and a dedicated work space with a small town feel. With its blend of cozy charm and convenient location, The Cottage on Midland is the perfect place to stay while visiting.

Comfy Pinehurst Home near Golf w/ Ping-pong

Life in the Pines! This charming home, only 1.4 miles from the Pinehurst Golf Clubhouse, provides ample space to relax and unwind. With easy access to Southern Pines, Aberdeen, golf, events, and great dining is the ideal place for a get away. A 3 bedroom, 2 bath, home with a spacious yard, outdoor dining, and a ping pong table, nestled in the tall pines and a quiet neighborhood provides something for everyone during their stay in the Pinehurst area. (Note: Cameras - doorbell and driveway)

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, friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, a queen bed and small sofa bed. 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 for dogs. sorry, no cats.

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.

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.

Greenside Getaway️! Walk to Clubhouse and Cradle!

Welcome to the Greenside Getaway. This ground floor condo is located 60 yards from the 16th green of the Pinehurst #5 Course. A+ location! Walk to The Cradle, Clubhouse, Village Square and the Fair Barn. Enjoy your favorite beverage while enjoying the view from the back patio that provides NonStop golf action! You can see 4 holes of Pinehurst courses! 4 Full beds with gel memory foam mattresses. The kitchen is fully stocked with everything you need! Pet Friendly!

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!

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!

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!

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.

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.

Isle of the Pines! 1 mi. from Village of Pinehurst

Isle of the Pines is a family owned home with lots of thought put into the experience we want to offer our guests. We pride ourselves on the inviting space we provide through offering luxury amenities such as a fully equipped kitchen, abundantly stocked coffee bar, toiletries upon arrival, several family oriented games, and so much more!. We want you to feel like you have walked into your home away from home!