Family-friendly holiday rentals in Pinehurst

Juniper Pines Cottage

A very nice place to stay! Nestled in a peaceful, yet convenient area near Pinehurst "home of golf", North Carolina, our cottage invites the traveler to a pleasantly rustic setting. Built in 1943, our lovely cabin is completely renovated and filled with country charm. ATTENTION!!! PLEASE READ THIS & HOUSE RULES BEFORE SENDING INQUIRY. *PROFILE VERIFICATION MUST INCLUDE GOVERNMENT ID (ie, state issued license) *FOR THE HEALTH & SAFETY OF ALL GUESTS, WE MAINTAIN A NO PETS, NO EXCEPTIONS POLICY.

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

Unwind in the privacy of this adorable tiny-home! 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, shower with tankless water heater a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge w/ 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!

Long Drive On No. 5 - 1BR Condo, GREAT Golf Views

Renovated, centrally located condo in Pinehurst - only a 10 minute walk to the Pinehurst Golf Clubhouse! "Long Drive On No. 5" is a newly renovated, second-story one-bedroom condo perfectly located on hole #16 of Pinehurst No. 5 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy & luxurious finishes combined with an excellent location make this condo perfect for a weekend golf getaway or an extended stay!

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.

* Top Rated - Guest Fave - Golf Front Condo *

Welcome to the heart of Pinehurst! This clean and cozy ground-floor condo is ideal for golf trips, weekend getaways, or longer stays. Enjoy a well-stocked kitchen, comfortable furnishings, and a screened porch with peaceful fairway views - a prime spot for morning coffee or evening wine. Super close to the Village, great dining and shops, the Fair Barn, harness track and Pinehurst Resort; just 10–15 minutes to Southern Pines and Aberdeen. Quiet, walkable, and a reliable guest favorite!

Entire Condo · Greenview Retreat · Walk to PCC

Beautiful 1BR/1BA retreat in Pinehurst with stunning Course #5 views. Enjoy full access to the entire condo with complete privacy—your bucket-list destination and home to the US Open. Perfect for couples, golfers, or medical professionals. Walk to Pinehurst Country Club, and stay close to shops and hospitals (first health of the Carolinas). Fully equipped with fast Wi-Fi, New TV, dedicated workspace, and in-unit laundry. Long-term stays welcome, with discounts available.

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.

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!

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.

Downtown Nook (Historic Area)

LITERALLY steps from the quaint downtown of Southern Pines. This small but cozy space has a private entrance, comfy bed, TV, it's own HVAC and a bathroom with a shower. It is perfect for a short stay! No coffee pot, but Swanks coffee shop is 1.5 blocks away! No fridge, but restaurants abound starting 1/2 block away! No need to drive after a night out.....walk to the Nook to sleep! Please note the price point for this little gem reflects it's AMAZING location!

Water Oaks Cottage - Near Pinehurst Country Club

Three blocks by foot, bicycle or golf cart from the Carolina Hotel, deemed in 1901 the “Queen of South”, with its fine dining, entertainment, highly acclaimed “Spa at Pinehurst”, restaurants and shops of Pinehurst Village. Straight down from this grand resort by lovely promenade is the world-famous Pinehurst Country Club and renown “Number 2” championship golf course. A few blocks further, the 111 acre equestrian facility and historic Pinehurst Harness Track.

Golf Resort, Private Entrance, Bath & Kitchenette

This Condo is located on Talamore Golf Resort and is minutes away from many world class golf courses, to include Pinehurst Resort. Approximately 40 minutes to Fort Bragg for Military/DOD civilians who are TDY or house hunting; 4 miles to First Health Moore Regional Hospital for travel nurses; 2.5 miles to Sandhill community college; Reservoir Park is a 250 yard walk from the front door and includes a 95 acre lake, and more than 12 miles of Greenway Trails.