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

Southern Pines Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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$300
includes taxes & fees
21 Oct - 22 Oct
Cottage on Ridge- Short & Extended Stays

2. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
The price is NZ$314
includes taxes & fees
27 Sept - 28 Sept
Walkable Cottage, Pet Friendly with Fenced Patio

3. 11 E Pinehurst Manor

11 E Pinehurst Manor
Pinehurst
9.4 out of 10, Exceptional, (56 reviews)
"Nice place "
United States
john w.
The price is NZ$387
includes taxes & fees
27 Sept - 28 Sept
11 E Pinehurst Manor

4. The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
9.8 out of 10, Exceptional, (18 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$348
includes taxes & fees
28 Sept - 29 Sept
The Cottage at Knollwood Manor

5. 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, (47 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is NZ$384
includes taxes & fees
30 Sept - 1 Oct
Upstairs at the Estate - Across from SP Golf Club

6. The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.6 out of 10, Exceptional, (65 reviews)
"Always a wonderful stay!"
United States
Whitney S.
The price is NZ$456
includes taxes & fees
28 Sept - 29 Sept
The Lucky Lie - Entire Condo in Pinehurst

7. 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, (79 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$269
includes taxes & fees
28 Sept - 29 Sept
Located in # 6 golf community, close to First Health Moore Regional Hospital.

8. 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, (53 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
The price is NZ$378
includes taxes & fees
8 Oct - 9 Oct
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

9. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (59 reviews)
"Comfortable, convenient and all around enjoyable stay! Thank you to the hosts!"
United States
Jennifer G.
The price is NZ$524
includes taxes & fees
2 Oct - 3 Oct
Charming Downtown Cottage

10. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (97 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is NZ$539
includes taxes & fees
27 Sept - 28 Sept
Beautiful 1920's Craftsman-Downtown Southern Pines

11. The Perfect Lie in Pinehurst! A golfer's paradise!

The Perfect Lie in Pinehurst! A golfer's paradise!
Pinehurst
9.8 out of 10, Exceptional, (77 reviews)
"Wonderful stay and great experience with our host!"
United States
Matthew D.
The price is NZ$498
includes taxes & fees
28 Sept - 29 Sept
The Perfect Lie in Pinehurst! A golfer's paradise!

12. Studio Seven at Pine Valley

Studio Seven at Pine Valley
Pinehurst
9.6 out of 10, Exceptional, (11 reviews)
"Great stay"
United States
Lauren
The price is NZ$342
includes taxes & fees
5 Oct - 6 Oct
Studio Seven at Pine Valley

13. 19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3

19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
Pinehurst
8.8 out of 10, Excellent, (66 reviews)
"Great location and plenty of room for the two of us. Dog friendly neighborhood and very walkable. Nice work area off the dining room. Kitchen was stocked pretty well from a dishes/pans/glasses perspective. The only issues were: no hangers in any of the closets, no hair dryer, and the floors were really dirty (ruined a couple pairs of socks) so needed to wear shoes all the time."
United States
sheri m.
The price is NZ$360
includes taxes & fees
28 Sept - 29 Sept
19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3

14. The McCaskill Cottage in the Village of Pinehurst!

The McCaskill Cottage in the Village of Pinehurst!
Old Town Pinehurst
10.0 out of 10, Exceptional, (21 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is NZ$466
includes taxes & fees
5 Oct - 6 Oct
The McCaskill Cottage in the Village of Pinehurst!

15. The Mulligan Manor - 1BR/1BA Condo in Pinehurst

The Mulligan Manor - 1BR/1BA Condo in Pinehurst
Pinehurst
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Chris F.
The price is NZ$466
includes taxes & fees
29 Sept - 30 Sept
The Mulligan Manor - 1BR/1BA Condo in Pinehurst

16. 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, (29 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
The price is NZ$689
includes taxes & fees
27 Sept - 28 Sept
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!

17. Lakeside Condo on Pinehurst #5

Lakeside Condo on Pinehurst #5
Pinehurst
10.0 out of 10, Exceptional, (60 reviews)
"The place has an awesome location.. you can walk to the clubhouse if you wanted to... would definitely recommend this rental and i might do it again at some point "
United States
Jason W.
The price is NZ$531
includes taxes & fees
29 Sept - 30 Sept
Lakeside Condo on Pinehurst #5

18. 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, (19 reviews)
"Great place for a short golf getaway "
United States
Jay G.
The price is NZ$571
includes taxes & fees
29 Sept - 30 Sept
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

19. To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse

To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (92 reviews)
"I would highly recommend staying here when visiting Pinehurst and Southern Pines. It was one of the best VRBO experiences we have enjoyed."
United States
Jenny I.
The price is NZ$404
includes taxes & fees
7 Oct - 8 Oct
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse

20. 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, (53 reviews)
"Very clean, great location, minutes from Pinehurst main complex, perfect for our stay"
United States
James D.
The price is NZ$468
includes taxes & fees
28 Sept - 29 Sept
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Beautiful 1920's Craftsman-Downtown Southern Pines: This highly rated holiday home rental in Southern Pines is located next to a golf course, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Another good choice for your trip to Southern Pines is Luxury Golf Retreat - Simulator & Short Game Setup.

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.