A dense forest of tall pine trees with a clear sky.

Southern Pines Holiday Rentals

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Our top choices for Southern Pines holiday rentals

1. Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays
Southern Pines
9.8 out of 10, Exceptional, (50 reviews)
"Convenient, clean...a really cute place to stay."
United States
Jeffrey S.
The price is NZ$269
includes taxes & fees
10 Nov - 11 Nov
Cottage on Ridge- Short & Extended Stays

2. The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
Pinehurst
10.0 out of 10, Exceptional, (54 reviews)
"Very clean, great location, minutes from Pinehurst main complex, perfect for our stay"
United States
James D.
The price is NZ$463
includes taxes & fees
10 Nov - 11 Nov
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

3. The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.8 out of 10, Exceptional, (66 reviews)
"Always a wonderful stay!"
United States
Whitney S.
The price is NZ$450
includes taxes & fees
10 Nov - 11 Nov
The Lucky Lie - Entire Condo in Pinehurst

4. Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!

Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
Downtown Southern Pines
9.8 out of 10, Exceptional, (32 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!

5. Isle of the Pines, 1 mile from The Village of Pinehurst!

Isle of the Pines, 1 mile from The Village of Pinehurst!
Pinehurst
10.0 out of 10, Exceptional, (37 reviews)
"Great place, great location, great hosts."
United States
Aaron Z.
The price is NZ$667
includes taxes & fees
10 Nov - 11 Nov
Isle of the Pines, 1 mile from The Village of Pinehurst!

6. Upstairs at the Estate - Across from SP Golf Club

Upstairs at the Estate - Across from SP Golf Club
Southern Pines
10.0 out of 10, Exceptional, (48 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is NZ$333
includes taxes & fees
10 Nov - 11 Nov
Upstairs at the Estate - Across from SP Golf Club

7. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
9.8 out of 10, Exceptional, (16 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
The price is NZ$306
includes taxes & fees
10 Nov - 11 Nov
Walkable Cottage, Pet Friendly with Fenced Patio

8. Located in # 6 golf community, close to First Health Moore Regional Hospital.

Located in # 6 golf community, close to First Health Moore Regional Hospital.
Pinehurst
10.0 out of 10, Exceptional, (80 reviews)
"Nice cozy suite, just right for two people. Wife and I were in town for a nearby wedding and stayed here. Excellent place to stay."
United States
Thomas M.
The price is NZ$275
includes taxes & fees
10 Nov - 11 Nov
Located in # 6 golf community, close to First Health Moore Regional Hospital.

9. Studio Seven at Pine Valley

Studio Seven at Pine Valley
Pinehurst
9.8 out of 10, Exceptional, (16 reviews)
"Great stay"
United States
Lauren
The price is NZ$307
includes taxes & fees
15 Nov - 16 Nov
Studio Seven at Pine Valley

10. Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines

Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
Southern Pines
9.8 out of 10, Exceptional, (13 reviews)
"The host was very accommodating and we had a wonderful stay!The home is lovely and the host thought of everything, we wanted for nothing while we were there.The neighborhood is a great place to walk as is the downtown area!We can’t wait to visit again!"
United States
Michelle B.
The price is NZ$737
includes taxes & fees
10 Nov - 11 Nov
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines

11. Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (57 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
The price is NZ$365
includes taxes & fees
10 Nov - 11 Nov
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

12. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (62 reviews)
"Cutest little house!"
United States
Aletta W.
The price is NZ$516
includes taxes & fees
13 Nov - 14 Nov
Charming Downtown Cottage

13. 5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
Pinehurst
9.4 out of 10, Exceptional, (20 reviews)
"Great place for a short golf getaway "
United States
Jay G.
The price is NZ$671
includes taxes & fees
10 Nov - 11 Nov
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

14. NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn

NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn
Pinehurst
10.0 out of 10, Exceptional, (21 reviews)
"This place was absolutely amazing. I would definitely stay here again. Very clean and comfortable quiet and the location couldn’t have been better."
United States
Angela S.
The price is NZ$559
includes taxes & fees
15 Nov - 16 Nov
NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn

15. Stunning Lake front views in Pinehurst with a pool!

Stunning Lake front views in Pinehurst with a pool!
Pinehurst
10.0 out of 10, Exceptional, (113 reviews)
"Great place to stay!"
United States
Jody W.
The price is NZ$523
includes taxes & fees
11 Nov - 12 Nov
Stunning Lake front views in Pinehurst with a pool!

16. The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
10.0 out of 10, Exceptional, (21 reviews)
"This is a favorite place for us to stay when in Southern Pines. It is lovely, comfortable, the host is very helpful and the location is great. "
United States
Tracey W.
The price is NZ$387
includes taxes & fees
11 Nov - 12 Nov
The Cottage at Knollwood Manor

17. The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful home. Everything was great."
United States
Erik A.
The price is NZ$813
includes taxes & fees
10 Nov - 11 Nov
The Cowboy

18. The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst

The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
Southern Pines
10.0 out of 10, Exceptional, (4 reviews)
"A lovely home, just as described. Comfortable and well appointed. Highly recommend."
United States
Tracey W.
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst

19. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (100 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is NZ$537
includes taxes & fees
16 Nov - 17 Nov
Beautiful 1920's Craftsman-Downtown Southern Pines

20. Golf Front Longleaf Condo2BR/2BA

Golf Front Longleaf Condo2BR/2BA
Southern Pines
9.8 out of 10, Exceptional, (6 reviews)
"Everything was great! Host was very responsive. "
United States
Cindi N.
Golf Front Longleaf Condo2BR/2BA
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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Top Southern Pines Hotel Reviews

Find out more about Southern Pines

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?

Simulator & Unbeatable Golf Experience On 2 Acres!: This highly rated holiday home rental in Southern Pines offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Another good choice for your trip to Southern Pines is Beautiful 1920's Craftsman-Downtown Southern Pines.

How many holiday rentals are there in Southern Pines?

With 88 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?

Cultural attractions include Campbell House Galleries, whereas Reservoir Park is a spot to enjoy nature. Other places in town to visit include Mid Pines Golf Club and Pine Needles Golf Club.

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.