Vacation rentals with a pool in Southern Pines

4.98 out of 5 average rating, 236 reviews

A cozy space with a full kitchen, a seating area featuring a fold-out sofa, and a soft, colorful ottoman. Natural light is provided by overhead recessed lighting and a nearby window, while a sliding barn door adds rustic charm. A wall-mounted TV is visible.

Guesthouse in Carthage

Charming 1 bedroom guesthouse on 4 acres, hot tub

Our guesthouse sits on 4 quiet fenced acres about 100 feet from our home. We are about 15 minutes from Pinehurst. Our large, friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, a queen bed and small sofa bed. Coffee maker, wine fridge, fire pit with Adirondack chairs for evening glass of wine or to watch the fireflies. Saltwater pool from mid-May to Mid- Sep. Private two-person hot tub. Pet fee for dogs. sorry, no cats.

4.96 out of 5 average rating, 47 reviews

A comfortable living area features a sectional sofa with decorative throw pillows, accompanied by a wooden coffee table and two accent chairs. Large windows allow natural light to brighten the space, while a flat-screen TV is mounted on the wall, providing a cozy atmosphere.

Condo in Southern Pines

The Reynolds Villa-Golf/Couples Retreat

This newly remodeled NON SMOKING upper level Villa overlooks the Southern Pines Reservoir Park with glimpses of the the lake. This unit features 2 bedrooms and 2 baths with large walk-in showers. 2 large screen TVs, High Speed Internet, Black Stainless Appliances & leathered granite countertops. There is a sizable balcony that is a perfect spot for watching wildlife & outdoor entertaining. Clubhouse is public access and available for drinks, lunch and snacks. Talamore Pool is open to guests.

A spacious living area is presented with a large, dark sectional couch complemented by assorted cushions. A circular wooden coffee table is positioned in front, and natural light enters through expansive glass doors that offer views of the outdoor space. A small area rug and bookshelf enhance the comfort.

5 out of 5 average rating, 26 reviews

Pinehurst Playground on the Lake

Make Pinehurst your playground both on the links and at the lake! Bring your fishing pole and bathing suits for both our lake and pool access (May-Sept). We are located 1 mile from the famed Pinehurst Resort which is home to the 2024 US Open. Numerous other courses are within a 30 minute drive. There is no shortage of quality golf around here! Our place is perfect for a group golfing weekend, a family trip, US Kids golf tournaments, or a weekend spent shopping and enjoying the spa.

Guesthouse in Southern Pines

A spacious bedroom showcases a contemporary design with a large bed adorned in a black and white patterned duvet. A cozy seating area with bright pillows is positioned beside the bed. A wall of shelves displays decorative items, with lamps providing warmth and a pleasant ambiance.

4.98 out of 5 average rating, 52 reviews

Charming Getaway Carriage House with pool

Welcome to our peaceful guesthouse in Southern Pines, NC! This contemporary retreat offers a serene escape with a pool, charming gazebo, and stunning views of the championship golf course, Pine Needles. The spacious unit is decorated in a modern style, providing a comfortable and inviting ambiance. Relax poolside or take a stroll through the well-manicured grounds. Golf enthusiasts will delight in the proximity to the renowned course. Discover tranquility and luxury in this hidden gem.

4.98 out of 5 average rating, 92 reviews

The exterior of the home is framed by tall pine trees, with a long driveway allowing ample parking space. The two-story house features a light-colored siding and large front windows. Neatly trimmed shrubs and flower pots enhance the inviting curb appeal.

Home in Southern Pines

This is it! | Pool | Golf | Convenient to Town

Welcome to Lazy Afternoon in the Pines! We are nestled in a family friendly neighborhood in Moore County. Our location can't be beat. We are just a 5 minute drive from downtown Southern Pines, 15 minutes from Pinehurst, and 25 minutes from Ft. Bragg. Access the "Home of American Golf" from this spacious 5 bedroom 2.5 bath home. For the non-golfer, the home is equipped with every amenity you would expect from your own home plus Ping-Pong, darts, swimming pool, and local hiking trails.

4.94 out of 5 average rating, 36 reviews

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.

Home in Aberdeen

Convenient Golf Getaway

Welcome to your getaway in Aberdeen, NC! This spacious home is perfect for families or groups, featuring 3 bedrooms (1 queen bed, 1 full bed, 1 twin bed, plus an air mattress) and 2 bathrooms. Enjoy a private backyard and grill. Conveniently located just 15 minutes from Pinehurst's golf courses and 20 minutes from the Carolina Horse Park. Amenities include a fully equipped kitchen, laundry facilities, remote check-in/out, WiFi, and a private driveway. Book now for a relaxing stay!

4.94 out of 5 average rating, 132 reviews

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

**Pool CLOSED for the season** Welcome to Lakeview Landing, located in the heart of Pinehurst golf! With a second story view of Lake Pinehurst, guests can relax on the balcony or enjoy the community pool! This quiet neighborhood shares close proximity to several great golf courses and has easy access to the BEST parts of Pinehurst: historic downtown, Fair Barn + Harness Track, Pinehurst Resort + Clubhouse, etc. Plus, it's a quick drive to nearby Southern Pines + Aberdeen!

5 out of 5 average rating, 58 reviews

A spacious outdoor pool is surrounded by a chain-link fence, with several lounge chairs arranged along its perimeter. Lush green grass and trees frame the area, while multiple buildings can be seen in the background, contributing to a serene environment.

Apartment in Carthage

Golf Getaway, 5 miles to Pinehurst

Located under 5 miles from downtown Pinehurst—home to top-tier golf, upscale dining, and boutique shopping. This condo offers a full kitchen and a cozy living room. Each of the two bedrooms includes two queen beds, TVs, storage chests, closets, and private bathrooms. Ideal for four golfers, two couples, or a family of five. The balcony overlooks the pool, which is open seasonally for guest use. Laundry facilities are located in Buildings A & B.

A living area features comfortable seating arrangements, including a gray sofa and an accent chair. Natural light filters in through large sliding glass doors, which open to a balcony. A flat-screen TV is positioned on a white entertainment unit, with a decorative tray and plants on the coffee table.

5 out of 5 average rating, 135 reviews

Clean & Updated2BD, 2BA, Condo! Free Pool, WIFI

Hello and Welcome to the Magnolia Hideaway in Pinehurst ! It is our hope that our beautiful, renovated & very clean , condo is a place you can rest, unplug, and enjoy time together. VERY IMPORTANT ! PLEASE READ!! Beds can be converted into either 2 KINGS, 4 TWINS, or 1 KING and 2 TWINS. BED CONFIGURATIONS NEEDS TO BE REQUESTED AT TIME OF BOOKING! The STANDARD SET UP is as following: 1 KING BED in Main BDR and 2 TWIN BEDS in second Bedroom.

4.93 out of 5 average rating, 123 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.

Quiet, country living only 10 mins from shopping, restaurants, The Carolina Horse Park & golf! Enjoy the quiet neighborhood, the serene atmosphere & within 10 mins, you can be walking into 1 of many great restaurants or shopping centers. Enjoy grilling on the back deck, lounging in the pool or taking nice walk on the private road. House was completely remodeled 2 years ago & offers an open floor plan with 2 living rooms.

4.94 out of 5 average rating, 172 reviews

A well-maintained backyard features an inground pool surrounded by a manicured lawn. Red lounge chairs are positioned near the pool, while an inviting fire pit area with additional seating is set under the shade of nearby trees. Vibrant flowering bushes add color to the landscape.

Home in Southern Pines

Highland Hideaway/Pool & Fire Pit/$0 Cleaning Fee

Nestled in a peaceful neighborhood just a few miles from downtown Southern Pines and multiple world-renowned golf courses ⛳️ . A 3-bedroom / 2.5-bathroom home with a bonus room. Spacious open porches overlook an inground pool, perfect for those hot summer days, and a fire pit, perfect for relaxing during the evenings. This home is also a short drive to Fort Liberty and surrounding hospitals.

5 out of 5 average rating, 16 reviews

A serene bedroom features a spacious bed dressed in neutral tones, complemented by a nature-inspired accent wall of tall trees. Bedside lamps add soft lighting, and a wooden nightstand is positioned beside the bed. A light area rug covers the floor, enhancing the calming ambiance.

Condo in Jackson Springs

Par In The Pines

Forget your worries in this spacious and serene space. Completely remodeled and waiting for you to come and enjoy. This unit offers 2 large decks for enjoying the scenery overlooking the Foxfire golf course. Only 6.8 miles to the Pinehurst Clubhouse and Pinehurst Village. Come and enjoy amazing golf courses, shopping, restaurants and all the historic Sandhills area has to offer.

Popular amenities for Southern Pines rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a combination of comfortable seating, including a sleek sofa and armchairs. A modern coffee table sits atop a patterned area rug, with natural light filtering in through large windows. The open layout connects seamlessly to the kitchen area.

4.96 out of 5 average rating, 71 reviews

Cheerful Pinehurst home tucked away with a pool.

The outdoor living space features a patio with a seating area arranged around a circular fire pit. A heated pool is visible, surrounded by a spacious yard and shaded by tall trees, creating a private and relaxing environment.

Home in Southern Pines

4.79 out of 5 average rating, 61 reviews

Peaceful Southern Pines Home w/ Pool + Yard!

4.59 out of 5 average rating, 17 reviews

A spacious living area features a large flat-screen TV mounted above a wooden mantel. Two light gray sofas are arranged around a rustic coffee table adorned with a small floral centerpiece. Natural light streams through multiple windows, highlighting the inviting atmosphere.

Home in Foxfire

Luxurious Pine Manor: Golf Front Estate with Pool!

An open-plan living area features a spacious dining table surrounded by six upholstered chairs. A modern kitchen with an island is visible, showcasing new appliances and sleek countertops. Natural light streams in through windows, highlighting the warm wood flooring and neutral wall colors.

4.9 out of 5 average rating, 20 reviews

25 McQueen - 4 Bedroom House with Pool

5 out of 5 average rating, 28 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

An inviting outdoor space features a private pool surrounded by a concrete deck. Two lounge chairs are positioned under a large umbrella. A round table holds a decorative arrangement, while a pink inflatable float is visible in the pool.

4.92 out of 5 average rating, 37 reviews

Gorgeous Home | Private Pool | Close to Pinehurst

A private backyard pool area is illuminated softly under a twilight sky. Landscaped with lush shrubs and flowers, the scene features a swimming pool surrounded by a stone pathway and solar lights. The covered seating area and flag gently sway in the evening breeze.

5 out of 5 average rating, 45 reviews

The Pinehurst Paradise Pool Home

The exterior reveals a single-story home surrounded by lush greenery, with a gravel driveway leading to the entrance. A welcoming foyer is depicted, featuring a bench and potted plants. A covered porch showcases seating overlooking the landscaped yard, inviting outdoor relaxation.

5 out of 5 average rating, 24 reviews

Spacious property w/Pool & walkable to downtown

Condo rentals with a pool

A comfortable living area features a sectional sofa and two armchairs. A coffee table and round dining table are arranged with chairs, providing ample seating. Large sliding doors open to a balcony with views of Lake Pinehurst, framed by light-filtering curtains.

4.81 out of 5 average rating, 59 reviews

Pinehurst 2Bedroom 2Bathroom Condo with Lakeview

A game room is presented with a slate pool table positioned centrally, flanked by two framed vintage sport posters on the walls. Soft beige carpeting covers the floor, and natural light enters through large window treatments, contributing to the welcoming ambiance.

4.98 out of 5 average rating, 47 reviews

Perfect for families! Pool & year round lake views

The living and dining area features a light neutral palette, showcasing a spacious couch and a wooden dining table. Large glass doors provide natural light and access to a deck, offering views of surrounding greenery. A television stands opposite the seating area.

4.69 out of 5 average rating, 58 reviews

Renovated 2-bedroom/2 bath condo with pool access

The living area features a dining table surrounded by four chairs and a comfortable sectional sofa. Two armchairs are positioned by large glass doors that offer views of Lake Pinehurst. Soft natural light illuminates the space, complemented by neutral-toned décor.

4.93 out of 5 average rating, 80 reviews

Lakefront Pinehurst Condo 2BD/2BA - 114

A living area features a mix of comfortable seating options, including a brown leather armchair and a gray sofa with decorative cushions. A wooden coffee table sits on a patterned rug, while sliding glass doors offer views of the lake and access to the balcony.

4.93 out of 5 average rating, 15 reviews

Lake Pinehurst Perfection

A serene view of Lake Pinehurst is presented, with calm waters reflecting the surrounding trees and blue sky. The image captures several well-maintained buildings along the water's edge, creating a peaceful lakeside atmosphere.

4.97 out of 5 average rating, 86 reviews

Stunning Lakefront in Pinehurst with pool!

4.76 out of 5 average rating, 21 reviews

A view from the balcony captures the serene landscape of the golf course, framed by tall pine trees. A walking path meanders through the natural setting, leading towards the lush green of the fairway, with additional buildings visible in the distance.

Condo in Foxfire

Quiet Condo on Golf Course near Pinehurst-EV Plug

5 out of 5 average rating, 17 reviews

The family room features a comfortable sofa with decorative pillows, a circular coffee table, and a TV mounted on the wall. Natural light floods the space through glass doors leading to the balcony, with a colorful area rug enhancing the ambiance.

Condo in Carthage

Miles to Pinehurst or Ft. Bragg

Other vacation rentals with a pool

The exterior of the home presents a single-story structure with a combination of brick and wood siding. A well-maintained lawn is surrounded by neatly trimmed shrubs. A wide pathway leads to the entrance, framed by trees that provide shade.

4.94 out of 5 average rating, 17 reviews

Pinehurst Lake House - 4 Bedroom House with Pool!

4.82 out of 5 average rating, 17 reviews

The cottage's exterior features a welcoming entrance with a symmetrical design, framed by large, open shutters. The brick steps lead up to double doors, flanked by manicured bushes and trees. A well-maintained pathway adds to the inviting atmosphere.

Cottage in Pinehurst

Tremont Cottage | Private Pool | 2blk DT Pinehurst

A cozy living space is showcased, featuring a sectional sofa and a stylish accent chair. A dining table with four chairs is positioned nearby. Natural light from the windows enhances the warm wood flooring, while decorative elements add a welcoming touch to the atmosphere.

The Lake Tee

4.71 out of 5 average rating, 7 reviews

A spacious living room is seen, featuring a comfortable sofa with patterned cushions and two armchairs. A coffee table occupies the center, and a large wall-mounted TV is displayed. Sliding glass doors provide views of the outdoors, complemented by soft natural light.

Apartment in Pinehurst

Pinehurst Tee Time Retreat w/ Community Pool

The single-story home is surrounded by lush greenery and tall pine trees. A manicured lawn extends in front, complemented by well-maintained shrubs and a covered porch. Natural light brightens the exterior, showcasing a peaceful and inviting setting.

4.71 out of 5 average rating, 48 reviews

Idyllic Pinehurst Home, Near Golf Course!

A spacious living area is surrounded by large windows, offering views of the lakefront. The room features comfortable seating with dark leather sofas, a wooden coffee table, and a round dining table. Natural light fills the space, highlighting the hardwood flooring and modern decor.

5 out of 5 average rating, 43 reviews

Lakefront, Ground Level, 2BR, 2BA, 2020 Renovation

A scenic view of Lake Pinehurst is captured from a private deck, featuring outdoor seating in black metal. The tranquil lake stretches out in the background, bordered by lush greenery and homes along the shore. A private dock is visible on the right.

4.94 out of 5 average rating, 17 reviews

Pinehurst Lake House Retreat