Holiday rentals with a pool in Southern Pines

A fire pit surrounded by rustic Adirondack chairs is positioned on a stone patio. Soft glowing lights hang from a nearby tree, illuminating the tranquil atmosphere. In the background, a heated pool is visible, reflecting the serene night sky.

5 out of 5 average rating, 18 reviews

Walk to Village: Heated Pool Hot Tub Putting Green

Experience the magic of Pinehurst at The Enchanted Escape, a meticulously restored historic estate nestled on a private 1 acre lot, just a short stroll from the charming Village. This exceptional property offers a unique blend of vintage elegance and modern luxury, providing an unforgettable getaway for discerning travelers seeking space, privacy, and unparalleled hospitality. Perfect for groups, our property comfortably accommodates up to 10 adults across three beautifully appointed structures.

5 out of 5 average rating, 43 reviews

Flat in Aberdeen

Peaceful Studio Apt. slps 4, Pool, Hot Tub, Sauna

ULTIMATE getaway in NEWLY BUILT Studio apartment,Pool, Hot tub,&Sauna. Only 3 miles to Pinehurst Golf resort No 10. Have fun, relax & stay with the family/friends/pets in our studio apartment with private entrance. Sleeps 4 with 2 plush queen beds, kitchenette, bath, secluded amenities & shared laundry rm. Enjoy relaxing in our gorgeous pool or sunbath in the lounger. Unwind in the hot tub or Sauna. Street is a dead end and very quiet. Close to shopping and Southern Pines is only 5 miles away.

4.98 out of 5 average rating, 249 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.

Guest house 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.

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!

Our stylish ranch is perfect for large groups & retreats. Sleeps up to 20 with 10 beds. 5 bedrooms, 4 bathrooms on a 1 acre lot with a swimming pool, game room, firepit, and putting green! Our 1 acre lot feels secluded, but is close to everything! -5 mins to restaurants, nightlife and shops in Downtown Southern Pines -5 mins to Southern Pines Golf Club & Weymouth Center Venue -15 mins to Pinehurst Resort -10 mins to Pine Needles Lodge and Golf Club -10 mins to Mid Pines Inn & Golf Club

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, 29 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.

Guest house 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, 53 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.

5 out of 5 average rating, 30 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

5 miles from the Pinehurst Resort - Escape to a Lakeside Retreat - where comfort and adventure collide! This 4-bedroom gem sleeps 10 and boasts a cozy gas fireplace, big-screen TV, and free weight gym for staying active. Relax by the pool, paddle across the lake, or fish from the private beach. End your day by one of 3 outdoor fireplaces. With kayaks, a paddle boat and comfortable accommodations, fun and rest are endless. Perfect for unwinding or making memories—your retreat awaits!

4.95 out of 5 average rating, 39 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, 142 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!

The image features a golf simulator area with a virtual course displayed on a large screen, complemented by a putting green. A spacious outdoor pool is visible, alongside a cozy living space with comfortable seating and decorative elements. The exterior shows a beautiful patio surrounded by lush greenery.

5 out of 5 average rating, 56 reviews

Simulator & Unbeatable Golf Experience On 2 Acres!

Welcome to our luxury estate in the Pines! Comfortably sleeping 16+ at 5,000 sq ft of living space, this house is custom packed with insane amenities for the most epic golf trip experience! *Golf Simulator *Pool *Chipping Greens w/ 2 Tee Boxes Over a Pond *Huge 500 sq ft Pro Putting Green *Massage Chairs, Shuffleboard *Fire Pit, Outdoor Dining *Pool Table, PingPong, NFL Blitz, Darts *Poker Table *Two Refrigerators *Fire Pit *9x 55" TVs

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.

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.

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.

4.94 out of 5 average rating, 180 reviews

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.

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, 72 reviews

Cheerful Pinehurst home tucked away with a pool.

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.

4.98 out of 5 average rating, 96 reviews

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

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.

4.79 out of 5 average rating, 63 reviews

Peaceful Southern Pines Home w/ Pool + Yard!

A newly constructed guest house is set among tall pine trees on a gravel driveway. The light gray exterior features a centered front door with blue accents and two simple chairs placed on either side, providing a welcoming entrance.

Home in Pinebluff

4.67 out of 5 average rating, 6 reviews

Spacious house with pool

An inviting pool is positioned on a wooden deck, overlooking serene Lake Pinehurst. Lounge chairs, adorned with blue cushions, flank one side. Lush greenery and trees create a natural backdrop, enhancing the tranquil view of the water and sky.

4.79 out of 5 average rating, 19 reviews

235 SW Lake Forest - Pinehurst Lake House With Hot

5 out of 5 average rating, 46 reviews

The Pinehurst Paradise Pool Home

5 out of 5 average rating, 4 reviews

3BD Pinehurst Condo Family Friendly near Fair Barn

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

Apartment 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.

4.83 out of 5 average rating, 63 reviews

Pinehurst 2Bedroom 2Bathroom Condo with Lakeview

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, 59 reviews

Renovated 2-bedroom/2 bath condo with pool access

4.67 out of 5 average rating, 3 reviews

Three Little Pines Condo 2BD 2BA and Seasonal Pool

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

The living area features hardwood floors with natural light flowing through large windows. A spacious gray sectional sofa is arranged around a coffee table, complemented by a dining table with light-colored chairs. Decorative plants add a touch of greenery to the space.

5 out of 5 average rating, 96 reviews

Renovated, Ground Level 2BR2BA, WiFi, Cable, Pool

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, 82 reviews

Lakefront Pinehurst Condo 2BD/2BA - 114

A cozy living area is presented with a blend of soft gray sofas and armchairs arranged around a wooden coffee table. A decorative rug lies beneath, complemented by a wall clock and tasteful wall art. Natural light enhances the welcoming atmosphere.

5 out of 5 average rating, 136 reviews

Ask forJanuary special. Newly updated 2BD, 2BA

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.

Apartment in Foxfire

Quiet Condo on Golf Course near Pinehurst-EV Plug

Other holiday 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!

An open living space features a sectional sofa with yellow cushions and a decorative throw, paired with a plush ottoman. A small round dining table sits nearby. A kitchen area can be seen in the background, complemented by warm wood flooring and natural light from large windows.

Flat in Southern Pines

Quiet and cozy! *Perfect studio you’ll love*

The lodge is presented from an aerial view, showcasing its expansive structure with a gray roof and white exterior. A welcoming porch with pillars is visible at the center, framed by manicured landscaping. Surrounding fields and trees add a serene natural backdrop.

Barn in Southern Pines

Luxury Barn Lodge - Farmstay, Horse Country, Golf

4.61 out of 5 average rating, 18 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!

Apartment in Jackson Springs

Condo w Golf, Pool, & Pickleball. 7mi to Pinehurst

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

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, 44 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.