Holiday rentals with a pool in Southern Pines

Mulligan Fair-Way, a golf retreat -Southern Pines.

Welcome to Mulligan Fair-Way, a golf-inspired retreat in the heart of Southern Pines, where every stay feels like a second shot at unforgettable memories. ⛳ Just like golf, the best experiences deserve a mulligan—and this is a place guests love coming back to, round after round. Perfectly located near some of the most iconic golf courses in the Sandhills, this home is designed for golfers, friends, and families who appreciate great company, relaxed vibes, and the joy of replaying a great trip.

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.

Peaceful Place sleeps 16 , Pool, Hot tub, Sauna

The ultimate getaway! 3 mi. from Pinehurst Country Club & close to So. Pines. Enjoy a relaxing & fun stay in a newly built home. This spacious home has 4 bd rooms, 3 baths, sofa sleeper,Kit./dinning/living rm, laundry. The sun rm has a Sauna & foosball table. Outside you can swim in the large pool, grill & relax in the lounge area with sofa, dinette and unwind in the Spa. The yard is fully fenced in by a 6 ft. Privacy fence. There is also a grill,swing set,trampoline, fire pit and chairs.

UnForegettable Stay in Southern Pines

Perfectly located to enjoy all that Southern Pines and Pinehurst have to offer⛳️ Sleeps up to 8 with 4 Queen Sealy Posturpedic beds with luxury linens.  All the bedrooms have 43" smart TVs and charging ports for your electronics.  A 65" smart TV in the living room is just the place to watch your favorite movies and sports.  Fully stocked kitchen.  Outdoor seating on the front porch and back deck.  Seasonal community pool. Garage game room including 10ft putting green, foosball and darts.

Pinehurst Golf Stay near Cradle & Resort | pool

Breathe in the calm of Pinehurst at this updated 3BD/2BA condo beside Course No. 5 — just minutes from the Cradle, Pinehurst Resort, Pinehurst Village, Fair Barn and world-class golf. Perfect for families and golf groups alike! Enjoy a fully stocked kitchen, cozy living space with a basket of games, and thoughtful family touches like a high chair and pack ’n play. Spend your days exploring the greens, shopping in the Village and watch the sunset through the pines from your private patio.

Luxury Golf Retreat•Pool•Spa•FirePit•NearPinehurst

Experience The Palmer, a private Southern Pines Luxury retreat overlooking the golf course. Enjoy a private saltwater pool, hot tub, and multiple outdoor spaces from the front porch to the back deck and porch. The backyard is strung with ambient lighting for effortless nighttime entertaining. The Palmer has large front and back yards, plenty of parking, and games for all ages. Minutes from Southern Pines, Pinehurst, dining, and shops, perfect for golf trips, families, or group getaways.

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.

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!

Convenient Golf & Private Pool 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!

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!

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.

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.