Family-friendly holiday rentals in Southern Pines

The exterior of a two-story cottage is shown, featuring a white clapboard façade with dark roofing. A covered porch is seen at the front, furnished with a small round table and four chairs, surrounded by landscaping with young plants and mulch.

5 out of 5 average rating, 129 reviews

New 5 Bedroom Cottage on Pine Needles Golf Course!

New construction home on the golf course of Pine Needles Course between Pinehurst and downtown Southern Pines. Ideal location, close to everything the area has to offer. This 5 bedroom and 3 bathroom cottage is ideal for golf outings and family friendly vacations. Everything you need to make your stay ideal and comfortable. Main level: 1 bedroom, 1 bath, living room, kitchen, dining, office space, walk in pantry, laundry room. Second floor: 4 bedrooms, 2 bathrooms, abundant closet space.

Guest suite in Southern Pines

A spacious bedroom features a king size bed with light bedding and two accent pillows. A cozy seating area is complemented by a decorative throw and a small table. Natural light enters through the windows, adorned with sheer and dark curtains. Artwork is displayed on the wall.

4.84 out of 5 average rating, 177 reviews

The Suite Life - In-Law Apt, Private Entry, Fenced

Renovated, pet friendly in-law suite (downstairs unit) with a private entrance and no shared living spaces. Large, shared fenced yard, and 1 mile to downtown So Pines, 6 miles to Pinehurst Resort, 13 miles to Carolina Horse Park. King size bedroom, small sleeper sofa, Keurig, a new kitchenette with oven, microwave, full size refrigerator, 50in Amazon Fire TV to link your accounts and independent thermostat. A washer/dryer makes it great for short term leases! Looking forward to hosting you!

Superhost

An inviting hot tub with soft blue-green lighting is positioned under a covered patio, surrounded by comfortable seating. A fire table emits a warm glow in the background, creating a serene atmosphere for relaxation. Soft curtains frame the area, enhancing the privacy.

4.92 out of 5 average rating, 106 reviews

SoPi Oasis | Hot Tub | Fire Pit | Game Room | Pets

Welcome to our amenity packed space with a modern design that welcomes golfers, families, and pets alike! (NO CHORE LIST FOR GUESTS!) Simply check your worries at the door, we will take care of the rest upon checkout! This meticulously designed space promises an unforgettable escape for golf enthusiasts and relaxation seekers alike. Unwind in the game room, relax around the covered fire table, or enjoy the serenity in our peaceful backyard oasis. Located at the center of the US Golf Mecca!

Tiny home in Southern Pines

A charming bungalow is set amidst tall trees, showcasing a screened porch with multiple windows. The exterior features a neutral-toned facade surrounded by greenery and landscaped grounds. Sunlight filters through the trees, creating a serene outdoor setting.

4.93 out of 5 average rating, 122 reviews

Crosswind Farm

Nestled on 17 acres in the middle of horse country, the bungalow is a peaceful getaway spot for golfers, riders and travelers who want to enjoy everything Southern Pines has to offer. Minutes from downtown Southern Pines (3 miles, about a 5 minute drive). There is a short queen bed as well as a pull out couch. It can comfortably fit 2 adults, with fitting up to 4 people total. Full kitchen, porch seating, and a beautiful view! *please note that this is considered a tiny house

A cozy sitting area is highlighted by a green sofa with accent pillows. A round wooden coffee table is positioned on a textured orange rug, while a colorful geometric wall provides a vibrant backdrop. A television and air conditioning unit are visible in the space.

4.96 out of 5 average rating, 255 reviews

Loft Cottage on Ridge Short & Extended Stays

This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. It is located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This loft unit has a private entrance from the top of the stairs with 1 bedroom (Queen) & 1 bath, a full kitchen, and shared laundry room downstairs in the back of the home. Unit features vintage kitchen! Come stay with us for a short stay or extended stay!

Guesthouse in Southern Pines

A small, light blue cottage is surrounded by greenery, set within a fenced area. A bright white door is framed by a simple wooden staircase. The front yard features a gravel pathway and grass, offering a peaceful outdoor setting.

5 out of 5 average rating, 106 reviews

Quiet and Safe neighborhood Studio for 2

Enjoy a peaceful stay in this fully furnished studio for two, located in a quiet Southern Pines neighborhood. Separate unit behind the main home, it offers a private key code entrance, queen bed, and a kitchenette w/ a hot plate and griddle. Step outside to your own private area with a fire pit. Just minutes from shopping, restaurants, breweries, golf courses, and movies. Only 15mins to the hospital, 20mins to Rockingham Racetrack, and 9mins to the Walthour Moss Fdtn

4.98 out of 5 average rating, 102 reviews

A spacious two-story building is set against a clear blue sky, featuring multiple windows and an inviting wooden staircase leading to the upper level. Lush green grass surrounds the structure, complemented by a tree and a wooden fence in the foreground.

Apartment in Vass

Horse Farm Retreat near Pinehurst & Southern Pines

Wake up in the heart of North Carolina horse country, surrounded by grazing horses and peaceful pasture views on a working equestrian farm just minutes from Pinehurst and Southern Pines. Private apartment only: 10 min to downtown Southern Pines 12 min to Pinehurst golf courses 12 min to Woodlake Country Club Ideal for Pinehurst golf trips, equestrian events, or Fort Liberty visits. Enjoy true Sandhills living with fast Wi-Fi, self check-in, and full comfort.

A cozy living room features a leather sofa complemented by colorful cushions. A wooden coffee table is set on a light area rug, with decorative items arranged on top. Dark green walls provide a backdrop for wall art and plants, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 116 reviews

The Gallery - 2 bd Boutique Southern Pines Cottage

Enjoy a uniquely designed experience at this centrally-located place - whether in town for golfing, riding, or simply enjoying our quaint southern town. Just a block from Broad street's restaurants, shops, breweries and theatre, this two bedroom, two story cottage (and art studio!) has everything you need to enjoy Moore County. Relax in any of our carefully curated rooms, or take it outside to our backyard/vineyard for a summertime BBQ or a cozy fireside chat.

The exterior of the DownTown Ace features a welcoming two-story structure with a dark gray roof and light gray siding. Lush green lawns are surrounded by mature trees, creating a serene environment. The entrance is framed by brick accents and a pathway leading to the front door.

4.93 out of 5 average rating, 100 reviews

The Downtown Ace

The DownTown Ace is just under a mile from downtown Southern Pines, offering easy access to a variety of golfing and dining options. We take pride in creating a welcoming space with luxury amenities designed for your comfort. Enjoy a fully equipped kitchen, a well-stocked coffee bar, premium toiletries upon arrival, family-friendly games, a queen-size air mattress, and much more! Our goal is to make you feel like you've stepped into your home away from home.

The charming exterior features a welcoming porch with an American flag hanging prominently. Two rocking chairs are positioned invitingly. Lush greenery surrounds the home, and stacked firewood is neatly arranged beside the entrance. A pathway of gravel leads up to the front steps.

5 out of 5 average rating, 116 reviews

Cozy Cottage - pet friendly, great location!

Enjoy a cozy and premium experience at this centrally-located place. Two minute drive to the Southern Pines downtown area, 15 minutes to Pinehurst, and just minutes from horse country. We have everything you need to have your dream stay in the Pines. Tons of amenities including: Fenced in backyard Outdoor patio with fire pit and grill Wood fireplace Smart TV Washer and dryer Desk workspace Fast WiFi Smart Thermostats 2 car driveway Full kitchen …and more!

A small outdoor patio is presented with a round table and four black metal chairs. Lush greenery surrounds the area, providing a calm setting. The exterior of the cottage is gray, complemented by a dark front door and a welcoming pathway leading to the entrance.

4.96 out of 5 average rating, 229 reviews

Charming Cottage in Downtown Southern Pines

Right in Downtown Southern Pines, Camellia Cottage is the perfect getaway! Walking distance to all of the wonderful restaurants, shops and breweries Downtown Southern Pines has to offer, and only minutes from some of the country's best golf courses! This 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your own private patio, walk around and take in the beautiful sights of this charming Southern town.

The entrance to the home is framed by tall pine trees, showcasing a well-maintained path leading to a welcoming front door. A modern gate and house number are visible, enhancing the overall appeal of the property.

4.97 out of 5 average rating, 232 reviews

Serene By the Greens

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!

Popular amenities for Southern Pines family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A warmly colored dining area is highlighted by a large round table surrounded by eight black leather chairs. Natural light enters through tall arched windows, complementing the rich orange walls and decorative white wainscoting. A classic chandelier hangs above, adding elegance.

4.98 out of 5 average rating, 171 reviews

The Ross Retreat - In Pinehurst

5 out of 5 average rating, 25 reviews

Privacy in the Pines + Hot Tub + Custom Fire Pit

4.99 out of 5 average rating, 87 reviews

A hot tub is situated on a wooden deck, surrounded by outdoor seating options including chairs and lounge chairs. A vibrant shaded canopy offers shelter. Brick walls of the home can be seen in the background, contributing to a welcoming outdoor space.

Home in Vass

Firepit, BBQ, Wheelchair ramp, SmartTV, King,Pets

4.99 out of 5 average rating, 238 reviews

A soothing hot tub is illuminated by soft blue lights, creating a calming ambiance. The surrounding area features a modern privacy screen, subtly highlighted by exterior lighting, enhancing the serene nighttime setting.

Home in Pinebluff

Hot Tub * King Bed * Putting Green * Amazing Golf

A spacious living area is shown, featuring a large sectional sofa and a mounted television. An arcade game machine and a classic pinball machine are positioned nearby. An outdoor pickleball court and a hot tub are visible in separate images, complementing the recreational options available.

4.95 out of 5 average rating, 65 reviews

Pickleball, Hot Tub & Poker Retreat Near Pinehurst

A game room with dark green walls features a large golf simulator screen displaying a scenic golf course. A spacious sectional couch in a warm yellow hue provides comfortable seating, while a dartboard and additional TV are visible on the walls.

5 out of 5 average rating, 54 reviews

6BR w/ Golf Sim Putting Green Hot Tub Sauna Games

An outdoor patio area features a large brick fireplace, surrounded by a spacious rectangular seating arrangement. Soft lighting from string lights enhances the atmosphere, and the green backdrop of trees adds a natural touch to the setting.

4.94 out of 5 average rating, 89 reviews

Tranquil Retreat w/ Hot Tub, Patio, 2 Living Rooms

The exterior of a spacious house is surrounded by tall pine trees, featuring a combination of stone and siding. A welcoming front porch with columns leads to a central entrance. Lush landscaping includes colorful plants and manicured lawns, providing an inviting approach.

4.87 out of 5 average rating, 108 reviews

The Mulligan House in Pinehurst!!!

Family- and pet-friendly home rentals

Superhost

A rustic tree house is elevated among towering pine trees, featuring a spiral staircase leading to a wraparound deck. The structure is constructed from wood, showcasing large windows that invite natural light, and a welcoming door that hints at the cozy interior.

Guesthouse in Southern Pines

4.84 out of 5 average rating, 272 reviews

Storybook Tree House- 2 Mins to Local Breweries!

4.96 out of 5 average rating, 115 reviews

The living area is adorned with two green armchairs, one featuring a decorative pillow. A small white table holds a lamp, and a door leads to the outside, allowing natural light to brighten the space. A window is positioned nearby, enhancing the openness of the area.

Cottage in Aberdeen

Close to Pinehurst Golf & Horse Park

Apartment in Southern Pines

A cozy living area is presented, featuring two tan accent chairs and a dark sofa. A wood coffee table is centered on a patterned rug. The kitchen area includes a bar with two brown stools, equipped with modern appliances and tasteful decor.

4.97 out of 5 average rating, 203 reviews

Boutique-Style Pet-Friendly Horse Farm | Fox Den

4.97 out of 5 average rating, 133 reviews

The single-story farmhouse is illuminated by warm lighting against a night sky. The exterior features a welcoming front porch framed by shrubs and trees, with a sign of a basketball hoop on the side. The spacious lawn is visible, bordered by soft grass.

Farm stay in Raeford

3 bedroom country home close to Horse Park

Guest suite in Southern Pines

4.95 out of 5 average rating, 119 reviews

The Century Suite - Upscale Comfort

Farm stay in Southern Pines

The exterior of the cozy barn cottage features a brick facade and white paneling, complemented by a shaded porch with seating. Two stable doors are visible, surrounded by lush greenery and tall trees, creating a serene country atmosphere.

4.99 out of 5 average rating, 208 reviews

Finally Home Farm Bed and Barn

4.94 out of 5 average rating, 251 reviews

A cozy yellow cottage is framed by a wide porch with white railings, offering a welcoming entry. Surrounding green grass leads to tall trees in the background, providing a natural and serene setting.

Cottage in Raeford

The Cottage at White Winds Farm

Guesthouse in Southern Pines

The exterior of the cottage features a light-colored facade with a gabled entrance. A gravel driveway leads to a nearby garage, while two chairs and a small table are situated on the front porch, surrounded by landscaping with trees.

4.86 out of 5 average rating, 126 reviews

Solitude at The Shire 255 - Unit D - Downtown!

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 176 reviews

Condo in Pinehurst

The Suite Spot

Townhouse in Southern Pines

5 out of 5 average rating, 38 reviews

UnForegettable Stay in Southern Pines

A rectangular pool with clear blue water is surrounded by a concrete patio. A pool ladder is visible on one end. In the background, a structure with stairs and a mobile home can be seen, along with several tall pine trees providing shade.

4.93 out of 5 average rating, 130 reviews

Country living 10 mins to Horse Park, Golf & Town.

4.93 out of 5 average rating, 167 reviews

A spacious community pool is surrounded by lounge chairs, with a pergola providing shade in the background. Lush trees line the area, and the clear blue water reflects the sunny sky, creating a serene outdoor setting for relaxation.

Condo in Pinehurst

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

5 out of 5 average rating, 54 reviews

The Pinehurst Paradise Pool Home

5 out of 5 average rating, 11 reviews

A spacious living area features a comfortable sectional sofa and a round coffee table on a soft area rug. A world map adorns the wall. Natural light fills the space through sliding glass doors, leading to an outdoor seating area surrounded by greenery.

Apartment in Pinehurst

Newly Renovated, lakeview with Pool!

4.95 out of 5 average rating, 22 reviews

Pinehurst Retreat | pool | Near Resort & Cradle

A private backyard is shown, featuring a swimming pool with clear blue water surrounded by a concrete deck. Lush green grass extends across the yard, with trees providing a natural backdrop. The house is visible in the background, enhancing the serene outdoor setting.