Holiday rentals with a patio in Pinehurst

The Ross Retreat - In Pinehurst

Your entire group will enjoy this central location to 40+ golf courses in Moore county with easy access to restaurants and close to grocery stores. This gorgeous home with custom woodwork and backyard oasis is the perfect retreat for families and golfers alike. Enjoy comfortable beds with down pillows and high end mattresses with mattress pads and a fully stocked kitchen in this newly furnished home. If you appreciate the little things like HEPA air filters and quite dishwashers, we got you.

Newly renovated farmhouse style open concept.

Completely renovated, stylish 3-bedroom condo is perfect for group trips & Junior golf families. Newly renoved with wide open floor plan in main living area. Gourmet kitchen, 3 incredibly comfortable bedrooms and 2 brand new stunning bathrooms. Includes private laundry room in condo, coffee bar, big screen TV’s in every room, built in bench area in kitchen, very spacious living and dining area off open concept kitchen, and screened in porch out back. Condo is walking distance to The Cradle.

Pineland Patio Golf & Game

Drive 2.3 miles to the Southern Pines Golf Club, 7.5 miles to the Pinehurst Resort! Enjoy entire 2500 sqft home with 4 br, 2 living areas, kitchen, 3 full baths, dining room, and a study. Relax outside on the bench swing beside the firepit on the charming brick patio under established longleaf pine trees. 2.5 miles from downtown Southern Pines, less than 1/4 mile from dog-friendly hiking trails on beautiful 500-acre Weymouth Woods State Park. 25 minutes to the Ft. Liberty Longstreet Gate.

⛳ Golf & Family Bungalow - Convenient to Village

Beautiful and very clean home located only 1 mile from Pinehurst Country Club and the Village of Pinehurst. Great indoor and outdoor living spaces make this bungalow retreat perfect for your visit to Pinehurst. Great for golfers, groups, and families. Happy to host remote workers or those looking to move to the area. Fully equipped kitchen (coffee, utensils, cookware), bedrooms (linens, comforters), and baths (soap, shampoo, conditioner) to make your visit a pleasure. 🌟🌟🌟🌟🌟

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.

Airstream in the Pines

Enjoy our 2005 Airstream International 19' CCD for a unique stay in Southern Pines! Airstream in the Pines is located on a quiet street just steps from the trailhead of Weymouth Woods Nature Preserve. 2 bikes are available for your use to ride the short mile down to the shops & restaurants of downtown Southern Pines. You will also be a 10 minute drive to several world class golf courses including Mid-Pines, Longleaf, Pinehurst No. 9, Pine Needles, & more.

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.

Timeless Tudor - In the heart of Southern Pines!

Consider this your home-away-from-home! Enjoy your visit to the "land of the pines" by staying in the Timeless Tudor. Capable of comfortably hosting groups of up to 10, this beautifully updated 100 year old home is located just two blocks from downtown Southern Pines and boasts—among its many favorable features—4 comfortable bedrooms, 2 and a half bathrooms, and a private backyard oasis.

Easy Walk to Downtown House-Par for the Course #2

Discover our three-bedroom cozy home in Golf Town, perfect for a guy's golf weekend or a family vacation. Located steps from downtown's restaurants, cafes, and shops, our house features three bedrooms, two and a half baths, and a spacious backyard. Enjoy walking to local attractions, relaxing or dining outdoors around town. Ideal for those who love golf, small-town charm, and convenience.