Vacation rentals with a pool in Southern Pines

Find and book unique homes with a pool on Airbnb

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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Guest favorite

A single-story home is showcased with pale yellow siding, complemented by dark shutters. Surrounding landscaping includes well-maintained bushes and trees. A paved driveway leads to a garage with a closed door, while two bins are positioned near the entrance.

Home in Aberdeen

5 out of 5 average rating, 11 reviews

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 with a pool 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!

Superhost

The backyard showcases a spacious inground pool surrounded by a brick patio, complemented by lush landscaping. The two-story house features a combination of brick and wood siding with multiple windows, enhancing the natural light. Lounge chairs are placed nearby, creating a relaxing atmosphere.

Home in Carthage

4.62 out of 5 average rating, 13 reviews

Welcome to the Castle, Private Pool spacious

Must be at least 25 to book. Rental Agreement and security deposit required. Additional guest fee over 6 guests No 3rd party bookings. Disclosed pet fee with approval, $500 undisclosed pet fee, $50/hr late check out fee. No one night reservations less, 5 min for holidays. Cancellation Policy 100% (less $100.00 cancellation fee) if cancellation occurs at least 60 days before arrival; No refunds within 60 days of arrival. $500 refundable security deposit required. POOL HEAT ADDITIONAL CHARGE

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

4.99 out of 5 average rating, 209 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 and friendly dogs greet you upon arrival and share the same fenced area as the guesthouse. Our barn conversion has a full kitchen, one queen bed and small fold out sofa. 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.

Top guest favorite

An open living area is presented, featuring a comfortable sofa and recliners. A dining table with four wooden chairs occupies one corner. Natural light filters in through sliding glass doors that lead to a balcony, surrounded by greenery. Decorative elements include two framed artworks and a potted plant.

Condo in Pinehurst

4.92 out of 5 average rating, 131 reviews

THE NEST, 2BDR 2BA, 2nd Floor, WiFi, Cable, Pool

Our condo is centrally located in the quiet and scenic Lakeview Condominium Community - only minutes away from Pinehurst Resort and CC and the charming Village of Pinehurst. Located on the second floor, this 2BR/2BA unit offers a very comfortable and restful stay. Whether you're taking in the gorgeous sunset from the balcony, a winding stroll through the community, or some down time at the private pool, our hope is that you find pleasure in every moment that you're here!

Top 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

4.95 out of 5 average rating, 112 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

A guest house with a welcoming facade is viewed from the pool area. The building features a classic design with light-colored siding and a sloped roof. A flag is displayed on the porch, and outdoor seating is arranged beside the pool against a lush, green backdrop.

Guesthouse in Southern Pines

4.94 out of 5 average rating, 207 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

Home in Pinehurst

5 out of 5 average rating, 38 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

Condo in Pinehurst

5 out of 5 average rating, 131 reviews

Newly renovated 2BD,2BA condo,Free Pool, Cable etc

We would like to say Hello and Welcome you to the Magnolia Hideaway! 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.

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

4.92 out of 5 average rating, 113 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

An inground pool with clear blue water is framed by lush greenery and vibrant pink flowers. The pool area includes a diving board, while a spacious lawn extends beyond. The background features a home with a large deck, offering inviting outdoor living space.

Home in Southern Pines

4.96 out of 5 average rating, 144 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

4.8 out of 5 average rating, 10 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.

Top guest favorite

A modern vanity area features a large mirror framed by geometric tiles in a soothing blue hue. A cushioned stool with a gold frame complements the sleek, dark cabinetry. Soft lighting enhances the stylish setup, offering an inviting space for personal grooming.

Condo in Pinehurst

4.95 out of 5 average rating, 108 reviews

The Suite Spot

This centrally located suite is the perfect spot for your next visit to Pinehurst. Come and enjoy the views from the back covered porch, book a tee time at one of Pinehurst’s world renowned golf courses, soak up some North Carolinian vitamin D and then take a dip in the pool, or simply stay indoors and let The Suite Spot be your sweet respite from the world.

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What guests are saying

The Pinehurst Perch

5 out of 5 average rating, 8 reviews6 months ago

Our family (including dogs) had a good stay for a horse event at the harness track. Condo was conveniently located, clean and had everything that we needed, even forgotten toiletries! Megan was a great host and extremely responsive, especially when the husband couldn’t quite find the condo.

Apartment in Pinehurst

What guests are saying

UnForegettable Stay in Southern Pines

5 out of 5 average rating, 26 reviews3 months ago

We enjoyed staying in this home. It was in a convenient location and also very quiet and private. The home is free from clutter and has all the needed amenities. We were able to be close to family and had the opportunity to walk around the Reservoir and eat at BHawk. We will definitely book this home again when we return to Southern Pines.

Townhouse in Southern Pines

What guests are saying

The Birdie Bungalow - fully fenced with pool

4.96 out of 5 average rating, 24 reviews4 months ago

This was a perfect place to stay with our pup for the weekend. It's a short walk to the entrance to the park with lots of fun trails for walking. Quiet, peaceful, but close to the towns in the area. Adorable indoor decor and great outdoor access - pool, fire pit, parking. The heater was malfunctioning before our stay and they were proactive in telling us about it (it heated, but made a loud sound while doing so). They offered a refund, and when we said we'd stay anyways they provided a space heater. We were able to use the space heater overnight and it worked just fine for such a small place. I'm sure they'll fix it for the next guests and we were pleased with their communicativeness and solution-oriented ideas! It was also our choice to stay despite the heater sounds. We were also not able to get the wifi to work but would still stay here again and recommend it to others!

Apartment in Southern Pines

What guests are saying

Lakeside Escape - 5 Miles from Pinehurst Resort

5 out of 5 average rating, 4 reviews2 weeks ago

This place is amazing! We had the perfect family getaway and Samantha’s place fit the bill perfectly. We’ve stayed at a lot of airbnbs and what I was soo impressed with was the quality of the beds. I don’t sleep that good at my own house. Pretty magical place to be honest. Book with extreme confidence!!

Home in Aberdeen