House holiday rentals in Southern Pines

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Top-rated house rentals in Southern Pines

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Guest favourite

Home in Southern Pines

5.0 out of 5 average rating, 101 reviews

Firefly Cottage with Firepit & Patio Swing

WRAP-AROUND PORCH LEADS TO COZY PATIO WITH FIREPIT! Check IG @fireflycottagesouthernpines for more local & cottage info! Charming 1600ft open concept 3 Bedrm/ 2 Bathrm craftsman cottage located 2 min from dwtn So Pines, 15 min from dwtn Pinehurst, 30 min from Ft Liberty, & min from renowned golf courses, & equestrian events. A fanstastic place for a girls wkend, golf trip, romantic getaway, or family reunion. Located on 0.5 acre lot, near great restaurants & breweries (see our guidebook).

Guest favourite

Home in Aberdeen

4.99 out of 5 average rating, 140 reviews

Retreat on Pine - Close to Golf & Horse Park

Luxurious, 3 bedroom/2.5 bath, new construction home in walking distance to Downtown Aberdeen ~ Beautifully furnished with the latest home fashions and technology, it's ready to be your home-away-from-home.Just minutes from world renowned golf courses, exquisite dining and enveloped by southern charm, this covetable area will not disappoint! Spend your day exploring all this area has to offer or Retreat on Pine and catch up on your rest and relaxation. 5 ~ star hospitality is what you'll Love!

Guest favourite

Home in Pinebluff

4.99 out of 5 average rating, 107 reviews

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay and Play Retreat! We are centrally located just minutes away from some of the areas greatest attractions such as Pinehurst No. 2 (8 Miles), Downtown Southern Pines ( 7 miles), Rockingham Dragway (14 miles), Carolina Horse Park (10 miles), and Fort Bragg (16 miles) . We're also surrounded by over 20 beautiful golf courses and a wide variety of dining options within 11 miles of this completely renovated home that has been created specifically for your comfort and enjoyment.

Guest favourite

Home in Pinehurst

4.92 out of 5 average rating, 108 reviews

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 favourite

Home in Southern Pines

4.99 out of 5 average rating, 145 reviews

Restored 1920s 2BR Cottage w/Bikes-DWTN So Pines

Experience downtown Southern Pines in a stylish fully restored early-1900's cottage. This home is conveniently located 4 blocks (4 min walk) from Broad Street, where you will find all the shopping, restaurants, and bars. The cottage is 5 minute drive to several world-class golf courses (Mid-Pines, Mid-South, Longleaf, Pine Needles, Pinehurst No. 9, Talamore) just to name a few... and only 10 mins away from the Village of Pinehurst and Pinehurst No.2. Cruise like a local on the free bikes!

Guest favourite

Home in Southern Pines

4.92 out of 5 average rating, 99 reviews

Quiet Cottage Downtown -Walk to it all!

Welcome to May Street Retreat! This beautiful home is located in downtown Southern Pines. It's only a short walk to all the shops, restaurants and nightlife; it's also next to many golf courses the Pines features! The backyard is fully fenced in for your pups, plus a fire pit to enjoy the gorgeous weather. There is a private driveway, and a covered carport. This is a quaint cottage has a dedicated work space, and a cozy living space to accommodate whatever the vibe of your retreat is!

Guest favourite

Home in Southern Pines

4.93 out of 5 average rating, 141 reviews

The Pines - Cozy, Large Deck with Fenced Yard

Enjoy a quiet stay tucked back in beautiful pine trees, less than a mile from downtown So Pines! 10 minutes to Pinehurst resort, great patio and large fenced yard shared with the lower unit (pet friendly). This upper unit has a full kitchen, King bedroom with en suite bathroom, two Queen bedrooms, a second bath, an electric fireplace in the living room, 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!

Guest favourite

Home in Southern Pines

4.99 out of 5 average rating, 150 reviews

Loft Cottage on Ridge ? Short & Extended Stays?

This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. It is located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This loft unit has a private entrance from the top of the stairs with 1 bedroom (Queen) & 1 bath, a full kitchen, and shared laundry room downstairs in the back of the home. Unit features vintage kitchen! Come stay with us for a short stay or extended stay!

Guest favourite

Home in Southern Pines

4.98 out of 5 average rating, 120 reviews

Premier Southern Pines Golf Oasis, Hot Tub Retreat

BEAUTIFUL 1930’S Traditional home with newly remodeled bedrooms,bathrooms and kitchen. Lounge in the Brand New Hot Tub after a round of golf at any of the Nearby World Class Golf Courses. Pine Needles, Long Leaf, Mid Pines, Talamore,to name a few. Perfect for Golf weekends,Wedding guest/Wedding party, friends and family reunion. Romantic getaways or Staycation with plenty of room to unwind, cook ,play and have your own space. Complimentary refreshments when you check in.

Guest favourite

Home in Southern Pines

4.97 out of 5 average rating, 174 reviews

Charming, newly updated Downtown Cottage

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 updated 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your newly landscaped patio, walk around and take in the beautiful sights of this charming Southern town.

Guest favourite

Home in Pinehurst

4.98 out of 5 average rating, 669 reviews

The Knotty But Nice Treehouse of Pinehurst

Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.

Guest favourite

Home in Pinehurst

4.98 out of 5 average rating, 111 reviews

Golf House Pinehurst on 5

Entire single family golf home on the 6th fairway of Pinehurst Course #5 Spacious 3 bedroom with 2.5 baths (Bedroom #1 - Queen bed; Bedroom #2 - 2 Double beds; Bedroom #3 - 2 Double beds). Eat-in Kitchen, Family Room, Living Room, Dining Room, Streaming TV, Wi-Fi Large Deck on back of house with Patio Table & Chairs. Overlooks hole 6 of Pinehurst No. 5 Golf Course ⛳️ Perfect for Golf buddy trips Family vacations, Ladies golf