Vacation rentals with a pool in Southern Pines

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Top-rated rentals with a pool in Southern Pines

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A private saltwater pool is surrounded by a spacious patio, with several lounge chairs positioned for relaxation. A shaded umbrella stands nearby, while lush greenery and a tranquil pond can be seen in the background, creating a serene outdoor setting.

Guesthouse in Carthage

4.98 out of 5 average rating, 224 reviews

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.

Top guest favorite

A crystal-clear swimming pool is surrounded by lush greenery and flowering trees. An elegant gazebo is visible in the background, adding a charming focal point to the outdoor space. The area is well-maintained, providing a tranquil setting for relaxation.

Guesthouse in Southern Pines

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.

Top guest favorite

Home in Southern Pines

4.98 out of 5 average rating, 88 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.

Top guest favorite

Home in Aberdeen

5 out of 5 average rating, 19 reviews

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!

Guest favorite

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

4.94 out of 5 average rating, 124 reviews

Lakeview Landing - 2 BD 2 BA Pinehurst Condo

**Pool OPEN 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!

Guest favorite

The guest house features a bright exterior with a welcoming porch adorned with black and white chairs. A flag is displayed, and lush greenery surrounds the area. The pool reflects sunlight, complementing the serene atmosphere of the jungle-like backyard.

Guesthouse in Southern Pines

4.94 out of 5 average rating, 208 reviews

Mystical Cottage

A warm cozy guest house with an open floor plan, high ceilings, and a wall of glass doors overlooking the pool and jungle like backyard of 3 acres. It has a large separate bath and complete kitchen. It was a perfect place for a completely secluded getaway ... less than 2.5 miles from the center of both Southern Pines and the Village of Pinehurst... 8 minutes from nearly every restaurant in the area. We are pet friendly, but charge a seperate $35 pet cleaning pet.

Top guest favorite

A well-maintained backyard area features a sparkling swimming pool with a safe railing. Lush flowering plants surround the space, complemented by vibrant pink blooms against a clear blue sky. Lounge chairs and a shaded table enhance the inviting atmosphere of this outdoor setting.

Home in Pinehurst

5 out of 5 average rating, 45 reviews

The Pinehurst Paradise Pool Home

Your family will be close to everything when you stay at this centrally-located home. Only minutes from the Pinehurst Resort & C.C. and village! I have been told my home is happy, fun, cozy, homey yet very clean and accommodating. Enjoy swimming in the pool, chipping golf balls on to the floating green, playing corn hole, and watching the outdoor TV while grilling out or lounging in a pool float! There is a covered gazebo with curtains and a gas fire pit.

Top guest favorite

A well-maintained backyard features a saltwater pool surrounded by lounge chairs and umbrellas. A hot tub is nearby, and a firepit is positioned on the patio. Lush greenery and trees provide a natural backdrop, enhancing the outdoor space for relaxation and recreation.

Home in Southern Pines

5 out of 5 average rating, 36 reviews

ThePalmerGolfGetaway*SaltWaterPool*HotTub*Family

Welcome to The Palmer – A 3-Bedroom, 2.5-Bath Retreat! Unwind in the hot tub or cool off in the saltwater pool. Gather around the firepit, or enjoy croquet, horseshoes, disc golf, and cornhole. Located just minutes from downtown Southern Pines and Pinehurst, enjoy local dining, shopping, plus over 40 renowned golf courses in the area, making it a dream destination for golf lovers. The Palmer offers endless opportunities to create unforgettable memories.

Top guest favorite

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

5 out of 5 average rating, 56 reviews

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.

Guest favorite

A view from the back deck showcases a well-maintained pool surrounded by a fenced area, with a spacious lawn extending towards the horizon. Tall trees provide shade, while a gentle sky adds to the serene country atmosphere.

Home in Aberdeen

4.93 out of 5 average rating, 122 reviews

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.

Top guest favorite

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

4.95 out of 5 average rating, 165 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.

Superhost

A spacious outdoor pool area features a clear blue pool surrounded by a concrete deck. Comfortable lounge chairs are positioned nearby. A well-structured patio area with ample seating is visible, alongside a grassy expanse and a charming two-story residence in the background.

Home in Foxfire

4.59 out of 5 average rating, 17 reviews

Luxurious Pine Manor: Golf Front Estate with Pool!

Ideal for groups! Welcome to a sanctuary of sophistication and comfort, where every detail is designed to make your stay truly exceptional. This stunning 6-bedroom residence offers the perfect setting for unforgettable getaways with friends, family, or any special group. Each bedroom is a private retreat, featuring its own en-suite bathroom for the utmost convenience and luxury.