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.

4.98 out of 5 average rating, 240 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.

Apartment in Southern Pines

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.

4.96 out of 5 average rating, 48 reviews

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, 28 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.

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, 93 reviews

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.

4.95 out of 5 average rating, 37 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!

4.93 out of 5 average rating, 138 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.

Flat 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 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

Clean & Updated 2BD,2BA, Condo! Free Pool, WIFI

Welcome you 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.

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, 175 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, 71 reviews

Cheerful Pinehurst home tucked away with a pool.

Superhost

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

4.59 out of 5 average rating, 17 reviews

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, 29 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 out of 5 average rating, 46 reviews

The Pinehurst Paradise Pool Home

New place to stay

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

An outdoor pool features inviting turquoise water surrounded by natural stone paving. Adjoining the pool area, a patio is furnished with several adirondack chairs. Soft lighting is provided by string lights draping from nearby trees, creating a serene atmosphere.

4.94 out of 5 average rating, 52 reviews

Your Private Clubhouse w/ Golf Simulator and Pool

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.

4.81 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

Superhost

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

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, 88 reviews

Stunning Lakefront in Pinehurst with pool!

5 out of 5 average rating, 18 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.

Apartment in Carthage

Miles to Pinehurst or Ft. Bragg

A bright living area is filled with natural light, featuring a comfortable seating arrangement with a sofa and decorative pillows. A glass coffee table sits on a colorful area rug, while a dining table is positioned nearby, framed by large windows showcasing views of the lake.

4.5 out of 5 average rating, 36 reviews

Lakeview Condo w/ Resort Pool: 2 Miles to Golf!

A serene view of a fenced seasonal pool area is seen, surrounded by lush greenery. A sunset casts a warm glow above, enhancing the tranquility of the scene. A sign indicating the pool's private status stands to the right, framed by neatly maintained shrubs.

5 out of 5 average rating, 3 reviews

Lakefront 3BR/2B near Pinehurst Resort

Other holiday rentals with a 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, 81 reviews

Lakefront Pinehurst Condo 2BD/2BA - 114

Superhost

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.

Flat in Pinehurst

4.71 out of 5 average rating, 7 reviews

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, 49 reviews

Idyllic Pinehurst Home, Near Golf Course!

A two-story home is set on a grassy area surrounded by trees. The exterior features beige siding, blue shutters, and a welcoming front porch with steps leading up. The driveway extends to the side of the house, providing ample parking space.

Home in Carthage

4.7 out of 5 average rating, 10 reviews

'Peacock Landing' in Vass: Game Room & Shared 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.

4.79 out of 5 average rating, 62 reviews

Peaceful Southern Pines Home w/ Pool + Yard!

A spacious two-story house features a combination of wood and stone accents. The driveway leads up to a three-car garage with dark doors, while lush greenery and trees surround the property, creating a tranquil setting.

4.92 out of 5 average rating, 12 reviews

Fire Pit + Patio: Spacious Southern Pines Retreat

A spacious living area features a large blue sofa, a wooden coffee table, and a flat-screen TV. Natural light flows through sliding glass doors, revealing a view of a private deck surrounded by trees. Light-colored walls and a textured ceiling are complemented by decorative elements.

Townhouse in Pinehurst

Pinehurst condo 3bed/2bath, family/golfer friendly

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.