House vacation rentals in Southern Pines

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Top-rated house rentals in Southern Pines

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Guest favorite

Home in Southern Pines

5.0 out of 5 average rating, 13 reviews

Place beyond the Pines - Walk to downtown

This cozy home is located within 4 blocks of all Southern Pines has to offer. Less than a 5 minute walk to our favorite coffee shop, yoga studio, as well as the best boutiques, restaurants and bars in town. Whether you’re unwinding after a long day on the links, coming home from a horse show, or resting after a training event, our house is here to welcome you home. Driving time: -Pinehurst Golf Resort (8 min) -Fort Liberty (35 min) -RDU International Airport (1 hour) -Weymouth Woods (4 min)

Nov 29 – Dec 6

G$31,002 GYD per night

Guest favorite

Home in Pinebluff

4.99 out of 5 average rating, 101 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.

Oct 4 – 11

G$48,196 GYD per night

Guest favorite

Home in Pinehurst

4.92 out of 5 average rating, 106 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.

Mar 6 – 13

G$35,861 GYD per night

Guest favorite

Home in Southern Pines

4.97 out of 5 average rating, 71 reviews

Bourbon On Bennett, Bespoke Townhome in DTSP

Now accepting 2024 US Open Bookings! This property offers optional concierge services - daily housekeeping, grocery delivery and pantry stocking, floral arrangements, and more. Approx. 6.6 miles to Pinehurst #2. Overflowing personality and convenience to all Downtown Southern Pines hotspots, the newly constructed Bourbon on Bennett awaits your next Southern Pines/Pinehurst stay. Beautiful furnishings, fully equipped kitchen. Two generous bedrooms with queen beds, 2 baths (one is en-suite).

Jan 18 – 25

G$31,373 GYD per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 142 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!

Jan 25 – Feb 1

G$30,445 GYD per night

Guest favorite

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!

Oct 27 – Nov 3

G$34,458 GYD per night

Guest favorite

Home in Southern Pines

4.99 out of 5 average rating, 146 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!

Feb 12 – 19

G$30,367 GYD per night

Guest favorite

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.

Nov 17 – 24

G$70,123 GYD per night

Guest favorite

Home in Southern Pines

4.98 out of 5 average rating, 172 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.

Sep 8 – 15

G$31,747 GYD per night

Guest favorite

Home in Pinehurst

4.98 out of 5 average rating, 663 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.

Oct 16 – 23

G$36,625 GYD per night

Guest favorite

Home in Aberdeen

4.95 out of 5 average rating, 22 reviews

Historic Martin House in Downtown Aberdeen

This is a beautiful historic home right in the middle of a quaint little downtown area in Aberdeen, NC. You can walk to pretty much anything you need: a small grocery, plenty of dining options and little boutiques spread all around. Come get away from the hustle and bustle and come relax in a great area filled with Southern hospitality! We are 10min away from Pinehurst Resort, Carolina Horse Park and plenty of golf and other activities!

Nov 17 – 24

G$29,500 GYD per night

Guest favorite

Home in Pinehurst

4.96 out of 5 average rating, 125 reviews

⛳️19th Hole🍸. Sleeps 10, Pool Table🎱 and Fire Pit

Spacious Pinehurst home, steps from Lake Pinehurst and adjacent to Pinehurst No. 3, down the street from the Fair Barn and No. 2! , this 5 bedroom, 3 bathroom home comfortably sleeps 10 adults, featuring 2 king bedroom retreats! Equally accommodating to golf foursomes, couples seeking a romantic getaway, or families on holiday! After a day on the course, enjoy Apres- golf cocktails around the pool table or fire pit!

Jan 20 – 27

G$62,640 GYD per night