Photo by Eric Mondres

Holiday Rentals in Southern Pines

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Holiday Rentals in Southern Pines

Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course

10.0 out of 10, Exceptional, (34)
"The house was perfect. We had no idea this place had so much history! Plenty of room for our 14 guests, both inside (Dining table sat all of us comfortably too!) and on the back patio/yard. The owner was helpful and sent a message during our stay, to see if we needed anything. You won’t be disappointed. We found a gem and will definitely book this again in the future. "
The price is €1,068
includes taxes & fees
1 Dec - 2 Dec
Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course

Two blocks from downtown! Charming, cozy home close to everything!

2.0 star property
10.0 out of 10, Exceptional, (4)
"The home was clean, uncluttered, and offered a fantastic fenced in yard for our 2 dogs. Our host was welcoming and kind. We are so glad we found this charming home!"
Two blocks from downtown! Charming, cozy home close to everything!

Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.

9.8 out of 10, Exceptional, (7)
"The house was more than adequate for us. We got more than we expected. Clean, comfortable and located near to the golf courses."
The price is €298
includes taxes & fees
26 Nov - 27 Nov
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.

Beautiful 1920's Craftsman-Downtown Southern Pines

10.0 out of 10, Exceptional, (54)
"We've stayed here several times. It is a wonderful place to stay when visiting family at Penick. We're able to walk up to visit and also stroll into town for dinner, music, entertainment, etc. This house is a gem! We'll be back."
The price is €309
includes taxes & fees
2 Dec - 3 Dec
Beautiful 1920's Craftsman-Downtown Southern Pines

The Pinecone Cottage - a Southern Pines escape

10.0 out of 10, Exceptional, (1)
"Great house and location. Host was very accommodating. "
The Pinecone Cottage - a Southern Pines escape

Upstairs at the Estate - Across from SP Golf Club

9.8 out of 10, Exceptional, (20)
"Great location for this well appointed and super comfortable property!"
The price is €194
includes taxes & fees
2 Dec - 3 Dec
Upstairs at the Estate - Across from SP Golf Club

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

9.6 out of 10, Exceptional, (5)
"House was nice, clean. Location was ok. "
Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!

10.0 out of 10, Exceptional, (35)
"The house is perfectly located for a Pine Needles, Mid Pines, Southern Pines golf trip. The town of Southern Pines has lots of good dining options just a walk or short drive away. "
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!

Cozy Southern Pines Retreat 1 Mi to Downtown!

9.2 out of 10, Wonderful, (14)
"The house has a warm lived in feeliing making it feel like home. Nice rooms and furniture thru out. Owners accommodated us making it easer to get ready for our daughters wedding."
Cozy Southern Pines Retreat 1 Mi to Downtown!

Historic Home w/hot tub, steps from everything!

10.0 out of 10, Exceptional, (18)
"Beautiful and spotless historic home located in a very central location with lots of things to do. The owner was incredibly helpful, and made our stay even more special. Would definitely re-book for future trip"
The price is €662
includes taxes & fees
2 Dec - 3 Dec
Historic Home w/hot tub, steps from everything!

Cottage on Ridge- Short & Extended Stays

9.8 out of 10, Exceptional, (20)
"Nice little place, not far from downtown Southern Pines "
The price is €166
includes taxes & fees
2 Dec - 3 Dec
Cottage on Ridge- Short & Extended Stays

Peaceful Southern Pines Home w/ Pool + Yard!

9.4 out of 10, Exceptional, (30)
"My family and I thoroughly enjoyed our stay here. Pristine, spacious and comfortable. "
Peaceful Southern Pines Home w/ Pool + Yard!

The Pine Needles Haven, < .5miles from Pine Needles Golf Course! - Monthly!

10.0 out of 10, Exceptional, (6)
"Very nicely remodeled and decorated. Water and snacks upon arrival. Even shower amenities in the bathroom. Super clean and comfortable. I don't know if it was just me, but the digital key pad was a little tricky to initially light up to see the numbers. The only feedback I have to give is to include information about the other rentals on the property and to mark designated areas for parking for each rental. When I pulled up there were two cars in the driveway, spread out, taking up most of the...
The Pine Needles Haven, < .5miles from Pine Needles Golf Course! - Monthly!

52 Longleaf: 2 BR, 2 BA Condominium in Southern Pines, Sleeps 4

9.4 out of 10, Exceptional, (42)
"Wonderful accommodations and perfect location! Right on the 9th hole fairway. Hopefully States will be at Longleaf in 2025, will definitely book this little cutie again! "
52 Longleaf: 2 BR, 2 BA Condominium in Southern Pines, Sleeps 4

"Peace On Wheels" Sleeps 4 Comfortably w/Outside Entertainment

10.0 out of 10, Exceptional, (1)
"Had a short 2 night stay. Host was extremely helpful in arranging entire camping experience."
"Peace On Wheels" Sleeps 4 Comfortably w/Outside Entertainment

Mystical Cottage in Southern Pines

9.8 out of 10, Exceptional, (38)
"Well kept pool and spacious cottage. Allen is an attentive and gracious host."
The price is €251
includes taxes & fees
2 Dec - 3 Dec
Mystical Cottage in Southern Pines

Cozy Southern Pines Retreat 1 Mi to Downtown!

2.0 star property
Cozy Southern Pines Retreat 1 Mi to Downtown!

This is it! | Pool | Golf | Convenient to Town

10.0 out of 10, Exceptional, (12)
"everything was as promised clean ,spacious, communications was great between owners and myself. if we return next year this is where we will stay "
This is it! | Pool | Golf | Convenient to Town

Suite Cypress Golf Hideaway. Minutes from Downtown

9.4 out of 10, Exceptional, (14)
"The townhouse is an end unit which provides additional privacy. It was furnished nicely and was neat and clean. The check in and out processes were easy. Overall, this is a great rental close to many golf courses, restaurants, and shopping."
The price is €354
includes taxes & fees
26 Nov - 27 Nov
Suite Cypress Golf Hideaway. Minutes from Downtown

Now available during the US Open

10.0 out of 10, Exceptional, (11)
"This place is ideal for large group of golfers. Accommodations work for large groups interested in large group meals and plenty of places to hang-out and catch-up. The only drawback was no large screen TV( which we knew going into rental, so for us it was not a negative). We did not mind as the group was playing 36 holes of golf per day and re-connecting each evening."
Now available during the US Open
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Southern Pines you may be interested in

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

2.5 star property
7.6 out of 10, Good, (915)
"Lacking in much needed maintenance in the rooms. Appears cutting corners is how they keep the rates down. It was good enough for the money"
The price is €73
includes taxes & fees
1 Dec - 2 Dec
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel

2.5 star property
9.0 out of 10, Wonderful, (743)
"Rooms were clean, staff friendly, and breakfast was above par!"
The price is €106
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

2.0 star property
7.6 out of 10, Good, (899)
"We have used the property in the past. No problems"
The price is €78
includes taxes & fees
1 Dec - 2 Dec
Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there holiday rentals in Southern Pines?

Yes, there are holiday rentals close to the most popular sights in Southern Pines, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Southern Pines. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Southern Pines has to offer?

Peaceful Southern Pines Home w/ Pool + Yard!: This highly rated holiday home rental in Southern Pines offers a fireplace, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Southern Pines?

With 92 Expedia holiday rentals, you're guaranteed to find just the right place for your Southern Pines stay.

What can I see and do in Southern Pines?

Explore the area and cultural attractions such as Seagrove Pottery of the Sandhills, or visit one of the family-friendly sights such as Carolina Horse Park. Other places in town to visit include Pine Needles Golf Club and Pinehurst No. 9.

What are holiday rentals like in Southern Pines?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southern Pines. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.