House holiday rentals in Southern Pines

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.

4.99 out of 5 average rating, 150 reviews

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.

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, 118 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.

A comfortable living room features a flat-screen TV mounted on the wall, alongside a stylish electric fireplace. A blue sectional sofa and a dark gray loveseat provide seating options. Natural light enters through the window, accented by cheerful throw pillows and wall art.

4.92 out of 5 average rating, 194 reviews

The Pines - Cozy, Large Fenced Yard (Upper Unit)

Enjoy a quiet stay tucked back in beautiful pine trees, less than a mile from downtown So Pines! 10 minutes to Pinehurst resort, great patio and large fenced yard shared with the lower unit (pet friendly). This upper unit has a full kitchen, King bedroom with en suite bathroom, two Queen bedrooms, a second bath, an electric fireplace in the living room, and a private washer/dryer making this a perfect fit for a longer stay, too. This home has all the essentials for a great getaway!

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.

4.97 out of 5 average rating, 233 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!

4.99 out of 5 average rating, 180 reviews

The kitchen features modern stainless-steel appliances, including a refrigerator and microwave. Granite countertops provide ample workspace, complemented by white cabinetry. A dual-basin sink is positioned in the center island, which enhances the open layout of the kitchen area.

Home in Aberdeen

Retreat on Pine - Close to Golf & Horse Park

Luxurious, 3 bedroom/2.5 bath, new construction home in walking distance to Downtown Aberdeen ~ Beautifully furnished with the latest home fashions and technology, it's ready to be your home-away-from-home. Just minutes from world renowned golf courses, Rockingham Dragway, exquisite dining and enveloped by southern charm, this covetable area will not disappoint! Spend your day exploring all this area has to offer or Retreat on Pine and catch up on your rest and relaxation.

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, 834 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.

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, 107 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 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, 106 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, 216 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, 209 reviews

Golfers’ Mid-Century Escape Minutes From Pinehurst

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!

A welcoming living area features a modern gas fireplace at its center, surrounded by built-in shelves holding decorative items. Two comfortable gray sofas are positioned across from a pair of patterned accent chairs, with small side tables nearby. Natural light enters through multiple windows.

4.95 out of 5 average rating, 183 reviews

⛳️19th Hole🍸. Sleeps 10, Pool Table🎱 and Fire Pit

Spacious Pinehurst home! Just steps from Lake Pinehurst and adjacent to Pinehurst No. 3, down the street from the Fair Barn and No. 2! This 5 bedroom, 3 bathroom home comfortably sleeps 10 adults, featuring 2 king bedroom retreats! Equally accommodating to golf foursomes, couples seeking a romantic getaway, or families on holiday! After a day on the course, enjoy Apres- golf cocktails around the pool table or fire pit!

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.

4.98 out of 5 average rating, 130 reviews

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.

Popular amenities for Southern Pines house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

Home in Foxfire

5 out of 5 average rating, 4 reviews

The Ultimate Golf Trip House - Pool & Pickleball

A spacious outdoor area features a large swimming pool surrounded by sun loungers with blue and white stripes. A covered cabana offers shaded seating, with a patio featuring a dining table and chairs. Lush greenery and a white fence enhance the private setting.

5 out of 5 average rating, 19 reviews

Pool*Sleeps 20*Stylish*Games*Close to Everything!

4.88 out of 5 average rating, 33 reviews

The spacious living area features large windows that allow natural light to fill the room. Comfortable seating is arranged around a substantial wooden coffee table, while a stone fireplace is set against a decorative wall. A warm, neutral color palette creates a relaxed setting.

Home in Aberdeen

Lakeside Escape - 5 Miles from Pinehurst Resort

4.93 out of 5 average rating, 124 reviews

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.

Home in Aberdeen

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

A spacious bedroom is furnished with a large bed featuring crisp white linens and decorative pillows. Soft lighting is provided by two bedside lamps. Natural light floods the room through sliding glass doors leading to a private outdoor space, framed by sheer curtains.

5 out of 5 average rating, 81 reviews

Southern Pines Getaway - Pool, Hot Tub & Fire Pit

5 out of 5 average rating, 46 reviews

The Pinehurst Paradise Pool Home

The entrance features a stone pathway leading to a welcoming front door adorned with a wreath. Potted plants flank either side of the entrance, and the surrounding greenery adds to the home's inviting exterior.

5 out of 5 average rating, 24 reviews

Spacious property w/Pool & walkable to downtown

Superhost

5 out of 5 average rating, 4 reviews

3BD Pinehurst Golf Condo. Near Fair Barn

Weekly house rentals

A unique tree house is set among tall pine trees, featuring a wraparound deck and steps leading to the entrance. The structure is elevated, with large windows allowing natural light inside. The exterior displays flags representing the United States and Maryland.

4.92 out of 5 average rating, 73 reviews

Chesapeake Tree House - golf front retreat

A modern kitchen features white cabinetry and dark countertops, complemented by a long wooden dining table surrounded by several metal stools. An open layout is visible, connecting to a hallway with a glimpse of the living area and additional room.

4.93 out of 5 average rating, 55 reviews

The Oakmont Cottage

A charming yellow cottage is framed by lush greenery and a low fence. The front porch is visible, featuring two chairs that invite relaxation. A blue sky with scattered clouds adds to the serene outdoor atmosphere, while shrubs and trees enhance the privacy of the yard.

4.81 out of 5 average rating, 16 reviews

Cottage Home in Southern Pines

A comfortable living room is presented, featuring a blue sofa with decorative pillows and a beige armchair. A round coffee table sits in front, with a soft area rug underneath. A painting adorns the wall, and natural light illuminates the space.

5 out of 5 average rating, 28 reviews

Slice of Southern Heaven! Serenity Pines Cottage

An inviting backyard space features several blue Adirondack chairs arranged around a stone fire pit. The house, sporting a yellow exterior, is visible in the background, complemented by lush greenery and a clear area for outdoor activities.

4.94 out of 5 average rating, 62 reviews

Downtown So. Pines - sleeps 8, walk to town.

The wrap-around deck is lined with wooden bar-height chairs, providing comfortable seating. Soft ambient lighting hangs above, creating a relaxed atmosphere. Views of the surrounding trees and neighboring buildings are visible, enhancing the outdoor experience.

4.85 out of 5 average rating, 67 reviews

Pinehurst No.6 Townhouse

The home features a classic architectural design with a light-colored exterior and a welcoming front porch. Two decorative lamps flank the entrance, and a spacious driveway leads to an attached two-car garage. Surrounding landscaping includes well-maintained grass and shrubs.

5 out of 5 average rating, 8 reviews

Cozy golf getaway!

5 out of 5 average rating, 70 reviews

Sunny Pinehurst Retreat

Private house rentals

5 out of 5 average rating, 18 reviews

Charming Downtown Corner Cottage - Dog Friendly!

5 out of 5 average rating, 53 reviews

19th Hole - Pickelball, Park, Downtown, Sim Access

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, 88 reviews

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

A spacious living area features high ceilings and floor-to-ceiling windows providing ample natural light. Comfortable seating includes two plush armchairs and a cozy sofa, arranged around a coffee table. A gas log fireplace is positioned beneath a wall-mounted TV, creating a welcoming atmosphere.

5 out of 5 average rating, 56 reviews

Million $ Golf-front view + 3 Master BR + Peloton

A modern kitchen features gray cabinetry and marble countertops, creating a clean and sophisticated look. Three wooden stools are arranged at the island, and stainless steel appliances complement the room. Soft lighting highlights the elegant backsplash tiles, contributing to an open and inviting atmosphere.

5 out of 5 average rating, 29 reviews

Banjos Golf Retreat- In the heart of Pinehurst!

A dining area features a large black table surrounded by eight cushioned chairs. Light streams through multiple windows, illuminating the space. A modern pendant light hangs above the table, while a potted plant adds a touch of greenery to the welcoming atmosphere.

4.97 out of 5 average rating, 38 reviews

Timeless Tudor - Walkable to Downtown!

A charming two-story cottage is featured in the image, showcasing light blue shingles and a welcoming front porch with rocking chairs. The pathway is bordered by landscaping, leading up to the entrance. Natural light filters through the trees, creating dappled shadows on the ground.

5 out of 5 average rating, 54 reviews

Newly remodeled Downtown Cottage-walking distance

A covered outdoor space features two hanging chairs and a dining table with comfortable seating. Soft lighting is provided by string lights above, creating a cozy atmosphere. In the background, a hot tub is visible, surrounded by natural vegetation.