Family-friendly holiday rentals in Pinehurst

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.

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.

- Guest Favorite - Peaceful Pinehurst Golf Condo

Welcome to Pinehurst! This clean and cozy ground-floor golf-front condo is ideal for golf trips, weekend excursions, longer visits, even staycations. Enjoy a well-stocked kitchen, comfortable furnishings, attractive decor and a screened porch with peaceful fairway views. Very close to the Village, prime dining and shopping, the Fair Barn, harness track and Pinehurst Resort; just 10–15 minutes to downtown Southern Pines and Aberdeen. Quiet, walkable, welcoming, and a perennial guest favorite!

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.

Location is everything !

Location! Cozy efficiency located in the heart of Golf And Horse country! Just 30 seconds (for real) to the main traffic circle which takes you to great restaurants, shopping, hospital (FirstHealth Moore Regional 1.5 miles away) and, of course, golfing!! The efficiency offers a private entrance, full bed, bathroom w/ shower, kitchenette, desk area, and outdoor seating. It is attached to my home so there is daily activity, but we welcome friendly engagement and will respect your privacy.

Cozy Studio in Historic Downtown

LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this charming small, yet quaint & cozy self contained studio/efficiency which is attached to a 1930's bungalow. Just steps to our idyllic downtown. (Literally 1 block). Guests will have the entire studio for their private use. (bed, bath, kitchenette) Central heating and air with thermostat 1 bed / 1 bath. Private entrance. Street parking. 'Strict' No Smoking Policy

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. It was recently remodeled, is well furnished, and we are constantly striving to upgrade and improve the space to make for a comfortable stay!

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 15 min to the famous Pinehurst Resort and Carolina Horse Park. Features a King size Nectar bed, Roku TV, WiFi, shower with tankless water heater, a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge, 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!

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.

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.

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, 2 local breweries and wine shops. We also offer housekeeping for only $ 10 a day. PLEASE LET ME KNOW, when booking IF YOU NEED THE SECOND BED.

Fairway Condo

This updated condo is located on the 17th hole fairway of the Pinehurst No. 5 Golf Course. It is perfect for golfers as well as travelers visiting Pinehurst area. It is minutes away by car to the Pinehurst Clubhouse and local restaurants. It features a 55 inch smart television in the living room, and a television and two double beds in each bedroom. It also features a custom built golf bag rack to keep your equipment safe and secure during the night.