Vacation rentals with outdoor seating in Whispering Pines

The Pines - Cozy, Large Fenced Yard (Upper Unit)

Enjoy a quiet stay tucked back in beautiful pine trees, less than a mile from downtown So Pines! 10min to Pinehurst resort, 17min to Carolina Horse Park, large deck and fenced yard shared with the lower unit (pet friendly). This single-level upper unit has a full kitchen, King bedroom with en suite bathroom, two Queen bedrooms, a second bath, an electric fireplace, and a private washer/dryer making this a perfect fit for a longer stay, too. This home has all the essentials for a great getaway!

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.

New 5 Bedroom Cottage on Pine Needles Golf Course

New construction home on the golf course of Pine Needles Course between Pinehurst and downtown Southern Pines. Ideal location, close to everything the area has to offer. This 5 bedroom and 3 bathroom cottage is ideal for golf outings and family friendly vacations. Everything you need to make your stay ideal and comfortable. Main level: 1 bedroom, 1 bath, living room, kitchen, dining, office space, walk in pantry, laundry room. Second floor: 4 bedrooms, 2 bathrooms, abundant closet space.

The Chatham House

The Chatham House is a privately-owned 3 bedroom/2 bath vacation home located in the famed Pinehurst #6 - just minutes away from the Village of Pinehurst shops and restaurants. This home-away-from-home features everything you need for a relaxing/fun vacation. Whether you have come to play some of the best golf courses in the world or have come for a fun family vacation, the Chatham House is your place to stay! Also great for Doctors and Nurses as First Health hospital is just minutes away.

- Guest Favorite - Peaceful Pinehurst Golf Condo

Welcome! This clean, cozy ground-floor golf-front Pinehurst condo is ideal for golf trips, weekend excursions, longer visits, even staycations. Enjoy a well-stocked kitchen, comfortable furnishings, and a screened porch with peaceful fairway views - perfect for morning coffee or evening wine! Super close to the Village, prime dining and shops, the Fair Barn, harness track and Pinehurst Resort; just 10–15 minutes to Southern Pines and Aberdeen. Quiet, walkable and a perennial guest favorite!

Cozy Pinehurst Retreat w/ Putting Green

Enjoy your Pinehurst stay in the family-friendly neighborhood of Village acres. The area is surrounded by The Greenway pedestrian and bicycling trail. The house is situated within 2 miles of downtown Pinehurst, Camelot Park, and Rassie Wicker Park, and is a short drive away from any of the many wonderful golf courses that Pinehurst has to offer. It was recently remodeled, is well furnished, and we are constantly striving to upgrade and improve the space to make for a comfortable stay!

Pinehurst Green - 2BD 2BA Golf Front Condo

Welcome to Pinehurst Green, located in the heart of Pinehurst golf! Our 2BD, 2BA condo is within walking distance of the Pinehurst clubhouse and the Village of Pinehurst. With a second story view on the Pinehurst #3 course, guests can enjoy hours of relaxation on the balcony overlooking the fairway, or stroll down to the historic Village for a cocktail, dinner or shopping. A 5 min drive to the Fair Barn and Harness Track and a 10 min drive to charming downtown Southern Pines.

A Golf Front SFH 3 BR 2 BA in Pinehurst # 6

A golf front great view 3 BR 2 Bathrooms with furnishings bungalow situated on Pinehurst #6. This house comes with WIFI and 4 smart TVS (Spectrum cable with golf channel). All 4 beds (1 K, 1 Q, 2 double) are with memory foam mattresses. sofa set, dining table for 8, 55'' smart TV on the wall and washer/dryer combination. Enjoy relaxing on the deck after a great round of golf. Amenities include a full kitchen, coffee maker, cookware, microwave, refrigerator.

Pinehurst #6 Garden Getaway

A warm welcome to our cozy 1 BR/1 BA apartment in the Pinehurst #6 community. It has a queen bed and a queen sofa bed if needed. We are close to the Village of Pinehurst and dozens of amazing Golf courses. We are less than 2 miles from First Health Moore Regional Hospital. Nearby you can enjoy shopping, dining, 2 local breweries and wine shops. We also offer housekeeping for only $ 10 a day. PLEASE LET ME KNOW, when booking IF YOU NEED THE SECOND BED.

Golfer's Paradise I Modern I Charming I 3BED/2BATH

Ideal for tournament stays and multi-day golf trips! Centrally located between Pinehurst and Southern Pines Accommodating up to 6 guests in exceptional comfort, our 3-bedroom, 2-bath Charming Pines Hideaway is ideally located within walking distance of Pine Needles Lodge and Golf Club. The great location provides easy access to nearby golf, horseback riding, hiking trails, kayaking, restaurants, and downtown districts of the Pinehurst/Southern Pines area.

Charming Cottage in Downtown Southern Pines

Right in Downtown Southern Pines, Camellia Cottage is the perfect getaway! Walking distance to all of the wonderful restaurants, shops and breweries Downtown Southern Pines has to offer, and only minutes from some of the country's best golf courses! This 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your own private patio, walk around and take in the beautiful sights of this charming Southern town.

Serene By the Greens

Relax in this peaceful, newly renovated space with a modern touch. Located in a quiet neighborhood next to Hyland Golf Club, this home offers the perfect retreat for golf lovers. Just one exit north of Pine Needles golf course (3.9 miles), it’s ideally situated for those attending the US Kids Golf World Championship at Longleaf Golf Club (5.9 miles away) or the US Men’s Open at Pinehurst #2 (8.9 miles away). Secure your golf getaway now—book today!