Photo by Eric Mondres

Southern Pines Holiday Rentals

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Holiday Rentals in Southern Pines

Property grounds
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!
10.0 out of 10, Exceptional, (16)
"Super quiet, very comfy and cozy 😊! The only problem we had, was having to go back to our stressful lives 😂. Definitely will come back?"
ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK!
Outdoor dining
Charming, newly updated Downtown Cottage
9.8 out of 10, Exceptional, (26)
"Great location. Close walking distance to the local eateries and shops. We had a great time here."
The price is NZ$514
includes taxes & fees
27 May - 28 May
Charming, newly updated Downtown Cottage
Pool
Peaceful Southern Pines Home w/ Pool + Yard!
9.4 out of 10, Exceptional, (20)
"To say this property meets all of the printed expectations is a simple response. ABOVE AND BEYOND what we expected! Plenty of comfort upgrades, little notes to help at each area we may have had issues and quick response from property helped us to settle in quickly and enjoy the lovely weather and quiet neighborhood!"
Peaceful Southern Pines Home w/ Pool + Yard!
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Property grounds
Loft Cottage on Ridge<br>? Short & Extended Stays?
10.0 out of 10, Exceptional, (7)
"A delightful little loft apartment in a perfect location. It had everything required for a month long stay while working in the area. Megan was fantastic with her communication, including suggestions for places to eat, drink, and things to see and do in the area. Will definitely book again when I’m back in Southern Pines."
The price is NZ$254
includes taxes & fees
30 May - 31 May
Loft Cottage on Ridge<br>? Short & Extended Stays?
Fridge, microwave, oven, stovetop
52 Longleaf - Rented during 2024 Open
9.2 out of 10, Wonderful, (35)
"Very quiet and cozy townhouse no amenities such as pool or guest house but my stay didn't require that. Enjoyed the serenity and was a good place to enjoy the unique North Carolina countryside."
52 Longleaf - Rented during 2024 Open
1 bedroom, desk, travel cot, WiFi
Cottage on Ridge- Short & Extended Stays
10.0 out of 10, Exceptional, (15)
"Cute place and perfect for an overnight stay in the area. The cottage had everything we needed, except for soap in the shower. Would stay there again, if in the area."
The price is NZ$282
includes taxes & fees
27 May - 28 May
Cottage on Ridge- Short & Extended Stays
Pool
Mystical Cottage in Southern Pines
9.8 out of 10, Exceptional, (36)
"The house was very comfortable and had everything we needed (except the WiFi wasn’t working but we lived without it). The location was great. Very close to our friends and the golf courses we were playing."
Mystical Cottage in Southern Pines
Interior
Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course
10.0 out of 10, Exceptional, (29)
"The stay was wonderful. Tyler was such a great host. We will certainly stay here again!"
The price is NZ$1,593
includes taxes & fees
26 May - 27 May
Knollwood Manor - Historic Mansion Overlooking the Famous Mid Pines Golf Course
Aerial view
Upstairs at the Estate - Across from SP Golf Club
9.8 out of 10, Exceptional, (14)
"I stayed for work in a rapid, dynamic schedule. The hostess was very kind and worked with me for my needs. She also was very responsive."
The price is NZ$336
includes taxes & fees
28 May - 29 May
Upstairs at the Estate - Across from SP Golf Club
Aerial view
Suite Cypress Golf Hideaway. Minutes from Downtown
9.6 out of 10, Exceptional, (12)
"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 NZ$613
includes taxes & fees
27 May - 28 May
Suite Cypress Golf Hideaway. Minutes from Downtown
Fridge, microwave, oven, stovetop
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
10.0 out of 10, Exceptional, (26)
"We had the best time! The house was absolutely perfect. No details were left unturned. Excellent parking for large trucks and close to the horse show. Loved it!"
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Fridge, microwave, oven, stovetop
Southern Pines Getaway w/Theater, Fire Pit & Pool
10.0 out of 10, Exceptional, (12)
"Fantastic time at a great property. The location was perfect and the host were second to none. Would highly recommend this property."
Southern Pines Getaway w/Theater, Fire Pit & Pool
Fridge, microwave, oven, stovetop
Guest House on 7 acres in horse country
10.0 out of 10, Exceptional, (5)
"The property was clean and very spacious! The owners are a joy; great communicators, helped us out by lending us chairs since we forgot ours, and provided us with delicious fresh eggs and a beer sampler that helped us decide which local places to eat! The dogs are so friendly and will only visit you if you want them to! This was a gem to discover because it’s one of the only places to stay close to the Carolina horse park, and it is a wonderful place to stay!"
Guest House on 7 acres in horse country
Private kitchen
Modern Luxury 5BR House in Downtown Southern Pines
10.0 out of 10, Exceptional, (6)
"Family and friends gathering for southern Pines wedding. Two blocks from our venue and everything was in order. Large spacious area/great room /kitchenfor the family to gather. Lots of bedroom space all very clean and tidy."
The price is NZ$1,093
includes taxes & fees
28 May - 29 May
Modern Luxury 5BR House in Downtown Southern Pines
Interior
Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!
10.0 out of 10, Exceptional, (2)
"Enjoyed our stay over the Christmas holiday. We choose the house based on its location. It’s easily walkable to downtown Southern Pines and a short drive to Pinehurst. The house is nicely decorated, bedrooms comfy and equally sized, kitchen well equipped, and the hot tub was very relaxing. The bathrooms are updated. The backyard is huge and would be a nice place to hang out in good weather. Check-out was simple. Hosts were quick to respond to communication. Great experience overall!"
The price is NZ$408
includes taxes & fees
29 May - 30 May
Golf Retreat -Walk or Bike to Downtown - Golf, Breweries, Restaurants!
Fridge, microwave, oven, stovetop
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
10.0 out of 10, Exceptional, (1)
"Door handle for tbe master loose master toilet almost overflowed had to plunge it. Other than that good place to stay"
The price is NZ$496
includes taxes & fees
27 May - 28 May
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Private kitchen
The Pine Needles Haven, < .5miles from Pine Needles Golf Course! - Monthly!
10.0 out of 10, Exceptional, (4)
"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!
Exterior
Beautiful 1920's Craftsman-Downtown Southern Pines
10.0 out of 10, Exceptional, (44)
"Would definitely stay here again"
The price is NZ$523
includes taxes & fees
1 Jun - 2 Jun
Beautiful 1920's Craftsman-Downtown Southern Pines
Property grounds
Reynolds Villa- Golf/Couples Retreat
10.0 out of 10, Exceptional, (13)
"Wonderful stay! Great setup and exactly as advertised. Enjoyed easy communication with the host, would highly recommend, and will look to stay here again."
Reynolds Villa- Golf/Couples Retreat
Interior
Cozy Southern Pines Retreat 1 Mi to Downtown!
3.5 star property
Cozy Southern Pines Retreat 1 Mi to Downtown!
Don't see what you're looking for?
See all available properties in Southern Pines
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.

Other types of properties in Southern Pines you may be interested in

Outdoor banquet area
Days Inn & Conf Center by Wyndham Southern Pines Pinehurst
2.0 star property
6.6 out of 10, (695)
"Very polite front desk help. Clean and safe feel to it. Great value for the money spent."
The price is NZ$112
includes taxes & fees
30 May - 31 May
Days Inn & Conf Center by Wyndham Southern Pines Pinehurst
In-room safe, desk, laptop workspace, iron/ironing board
SureStay Plus Hotel by Best Western Southern Pines Pinehurst
2.5 star property
7.6 out of 10, Good, (823)
"Great value for the price. Only downfall was the AC didn't cool very well."
The price is NZ$142
includes taxes & fees
25 May - 26 May
SureStay Plus Hotel by Best Western Southern Pines Pinehurst
In-room safe, desk, laptop workspace, blackout curtains
Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (696)
"Friendly and helpful staff, quiet and clean."
The price is NZ$195
includes taxes & fees
26 May - 27 May
Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southern Pines holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southern Pines. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southern Pines. Seeing all the best attractions is bound to make you fall in love with Southern Pines. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southern Pines short-term rentals, that won’t be hard to do.

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?

Charming, newly updated Downtown Cottage: This highly rated holiday home rental in Southern Pines is located in the city centre, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. Other favourite homes for rent in Southern Pines are ASK ME ABOUT DISCOUNTS BEFORE YOU BOOK! and Loft Cottage on Ridge
? Short & Extended Stays?
.

How many holiday rentals are there in Southern Pines?

With 111 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.

Recent reviews of Southern Pines properties
Expedia verified reviews