Holiday 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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Top Guest favourite

Guesthouse in Carthage

4.98 out of 5 average rating, 229 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 favourite

Condo in Pinehurst

5 out of 5 average rating, 24 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.

Top Guest favourite

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.

Guest favourite

Home in Southern Pines

4.98 out of 5 average rating, 92 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 favourite

Home in Aberdeen

5 out of 5 average rating, 26 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!

Top Guest favourite

Home in Aberdeen

4.97 out of 5 average rating, 32 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 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!

Guest favourite

Condo in Pinehurst

4.92 out of 5 average rating, 78 reviews

Lakefront Pinehurst Condo 2BD/2BA - 114

Beautiful Lake Pinehurst property only 1-2 miles from the clubhouse at Pinehurst Resort, the "Cradle" par 3, & the Pinehurst Spa. The community of Southern Pines is only a few miles away which offers additional fine dining & shopping. 1st floor condo Swimming Pool in Complex for guests open May-August. Smart TV in living room & primary room Wifi Keurig Coffee Maker Microwave Stack Washer & Dryer Unit Due to owners allergies, no pets including service animals are allowed.

Top Guest favourite

Home in Southern Pines

5 out of 5 average rating, 40 reviews

PrivateRetreat*Family*Events*HotTub*Pool*FirePit*

Welcome to The Palmer – A 3-Bedroom, 2.5-Bath Retreat! Unwind in the hot tub or cool off in the saltwater pool that is open year round. 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.

Guest favourite

Condo in Pinehurst

4.94 out of 5 average rating, 129 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!

Guest favourite

Guesthouse in Southern Pines

4.92 out of 5 average rating, 210 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 favourite

Home in Southern Pines

5 out of 5 average rating, 46 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

Guest favourite

Home in Aberdeen

4.93 out of 5 average rating, 123 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.