Family-friendly holiday rentals in Pinehurst

The living area features a comfortable gray couch with orange and gray accent pillows, paired with an accent chair in a geometric pattern. A rectangular coffee table sits on a soft area rug, illuminated by soft lamp light and natural light from the window.

4.99 out of 5 average rating, 169 reviews

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!

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4.94 out of 5 average rating, 163 reviews

A dining area features a wooden table surrounded by four chairs, set against a white brick wall with decorative letters spelling 'EAT.' Built-in cabinetry and a small wine cooler are present, contributing to the open and bright space illuminated by natural light from the window.

Villa in Pinehurst

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.

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A cozy bedroom interior features a queen bed adorned with fresh linens and stacked towels. Natural light enters through a window, illuminating the warm-toned decor and subtle artwork above the headboard.

4.97 out of 5 average rating, 153 reviews

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!

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Cottage in Southern Pines

The entrance to a charming cottage is framed by lush greenery and well-maintained landscaping. A stone pathway leads to the front door, while a gravel driveway guides visitors through vibrant shrubs and trees.

4.96 out of 5 average rating, 427 reviews

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!

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A welcoming living area features a gray sofa paired with two accent chairs, complemented by a round wooden coffee table. A patterned area rug adds warmth to the hardwood floor, while natural light filters through nearby window treatments.

4.95 out of 5 average rating, 269 reviews

Pinehurst Green - 2BD 2BA Golf Front Condo

Welcome to Pinehurst Green, located in the heart of Pinehurst golf! Our 2BD, 2BA condo is within walking distance of the Pinehurst clubhouse and the Village of Pinehurst. With a second story view on the Pinehurst #3 course, guests can enjoy hours of relaxation on the balcony overlooking the fairway, or stroll down to the historic Village for a cocktail, dinner or shopping. A 5 min drive to the Fair Barn and Harness Track and a 10 min drive to charming downtown Southern Pines.

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4.96 out of 5 average rating, 117 reviews

Golfers Getaway Pinehurst Modern 3 Bedroom House

It’s a beautiful day in Pinehurst! Come stay at our Golfers Getaway and enjoy everything this beautiful village has to offer. Whether you’re in town for the world-class golf or perhaps visiting family, our home has everything you need for a luxurious, comfortable stay. Located a mere 5 minute drive from the Pinehurst Country Club, as well as the Pinehurst Village shops and restaurants. The leisure choices in Pinehurst are endless. We look forward to welcoming you.

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A spacious living area features a gray sectional sofa with colorful cushions, complemented by a wooden coffee table. Floor-to-ceiling windows admit natural light, while the wood flooring adds warmth to the room. A dining area is visible in the background.

4.98 out of 5 average rating, 871 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.

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A spacious studio is illuminated by natural light, featuring two large beds with plush bedding. A comfortable seating area is positioned near a window, with views of the lush outdoors. Modern furnishings and a breakfast bar complement the inviting layout of the space.

4.97 out of 5 average rating, 150 reviews

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!

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A comfortable living room features a brown leather sofa, black-accented chairs, and a rustic coffee table on wooden flooring. Golf-themed decor is displayed on the wall, while light enters through nearby windows, enhancing the welcoming ambiance.

4.99 out of 5 average rating, 185 reviews

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

Enjoy your stay at a fully renovated 2BR/2BA condo right across from Pinehurst's historic Fair Barn and Harness Track. Situated on No. 5, a short approach shot from the Pinehurst Clubhouse, the Duffer's Drop has everything you need for your golf getaway. Relax on the porch overlooking No. 5, work on your culinary skills in the beautiful kitchen, or just catch some rest between rounds. The Duffer's Drop is the exactly what you're looking for!

KitchenFamilyAmenities

4.99 out of 5 average rating, 163 reviews

An open living space features brick flooring, a cozy seating area with a sofa and armchair, and a wall of bookshelves filled with books. A television is mounted on the wall, and warm light is provided by lamps. A dining table and kitchen island are present, enhancing functionality.

Home in Southern Pines

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.

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4.98 out of 5 average rating, 137 reviews

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!

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