Southern Pines Vacation Rentals from $149: Search Short-Term Rentals

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Our top choices for Southern Pines vacation rentals

1. Cottage on Ridge- Short & Extended Stays

Southern Pines

Jeffrey S.

$158 nightly

Aug 4 - Aug 5

Total with taxes and fees

2 bedrooms, iron/ironing board, travel crib, WiFi

2. Charming Downtown Cottage

Southern Pines

Jennifer G.

$264 nightly

Aug 4 - Aug 5

Total with taxes and fees

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

Southern Pines

Matea S.

$226 nightly

Aug 10 - Aug 11

Total with taxes and fees

4. Walkable Cottage, Pet Friendly with Fenced Patio

West Southern Pines

M T.

$151 nightly

Aug 17 - Aug 18

Total with taxes and fees

5. The Cottage at Knollwood Manor

West Southern Pines

Tracey W.

$210 nightly

Aug 8 - Aug 9

Total with taxes and fees

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

Pinehurst

Thomas M.

$135 nightly

Aug 5 - Aug 6

Total with taxes and fees

7. Beautiful 1920's Craftsman-Downtown Southern Pines

Southern Pines

Josh J.

$277 nightly

Aug 16 - Aug 17

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Southern Pines

Michelle B.

$373 nightly

Aug 10 - Aug 11

Total with taxes and fees

9. 11 E Pinehurst Manor

Pinehurst

john w.

$205 nightly

Aug 10 - Aug 11

Total with taxes and fees

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

Downtown Southern Pines

$335 nightly

Aug 10 - Aug 11

Total with taxes and fees

1 bedroom, desk, iron/ironing board, WiFi (free)

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

Pinehurst

Jack K.

$177 nightly

Aug 5 - Aug 6

Total with taxes and fees

Desk, iron/ironing board, WiFi (free), bed sheets

12. The Lucky Lie - Entire Condo in Pinehurst

Pinehurst

Andrew

$233 nightly

Aug 10 - Aug 11

Total with taxes and fees

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

Pinehurst

Britni H.

$184 nightly

Aug 17 - Aug 18

Total with taxes and fees

14. 19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3

Pinehurst

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property is very well located in connection to many nice restaurants and shopping opportunities as well as it being quiet and low key which was great for us"

Rita C.

$191 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

Pinehurst

Chris F.

$232 nightly

Aug 4 - Aug 5

Total with taxes and fees

16. The McCaskill Cottage in the Village of Pinehurst!

Old Town Pinehurst

Timothy

$243 nightly

Aug 6 - Aug 7

Total with taxes and fees

17. 5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

Pinehurst

Jay G.

$291 nightly

Aug 4 - Aug 5

Total with taxes and fees

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

Southern Pines

"We absolutely loved our stay here! The house is beautifully designed and just a short walk to downtown Southern Pines, where there are so many great restaurants and shops. Everything felt fresh, modern, and thoughtfully decorated with a fun mid-century vibe.Our favorite spot was definitely the Carolina room. It had the perfect cozy, dark-and-moody feel, with a huge window looking outside. Every morning we found ourselves sitting there with a cup of coffee, and it quickly became our favorite...

Andrea S.

$260 nightly

Sep 1 - Sep 2

Total with taxes and fees

19. Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8

Pinehurst

John M.

$289 nightly

Aug 5 - Aug 6

Total with taxes and fees

20. Bourbon & Bubbles with Speakeasy & Hot Tub in Downtown Southern Pines!

Southern Pines

Brandon L.

$478 nightly

Aug 17 - Aug 18

Total with taxes and fees

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Top Southern Pines Hotel Reviews

Holiday Inn Express Hotel & Suites Southern Pines by IHG

10/10 Excellent

"Everything at the hotel was a pleasant experience. The whole property was well-maintained and our room was clean. Staff was wonderful as well."

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

8/10 Good

"The house was a good size. The neighborhood was a little run down. I wouldn’t say you could walk to the restaurants- there aren’t sidewalks. The vent over the oven did not work- tried to cook bacon and it was a nightmare. The front door handle was not very secure. The showers were great and the AC was awesome!"

Beautiful 1920's Craftsman-Downtown Southern Pines

10/10 Excellent

"Great location near Southern Pines. Walking distance to several restaurants. weymouth Woods hiking trails literally two blocks away. Only a few minutes away from the Golf Course that we played. I would probably paint the front fence and do some things in the yard for curb appeal. Inside /older home but clean and you get what is advertised. Appliances, air-conditioning, all the important things have been updated/ large suite upstairs that we gave to our friends to stay in and they really enjoyed it. Almost instantaneous responses from the host answering my questions. Great experience for us. Great spacious property for a couple. It accommodated our two couples very well. Could also be used for a couple and 3 of their kids. depending on age.."

Loft Cottage on Ridge<br>? Short & Extended Stays?

8/10 Good

"It was a comfortable stay for 2 people. It is super quiet! Only issue is the parking. Only one spot for 2 units. One night we had to park on the street and walk in the dark to get to the back of the house (lights were on the steps) other than the parking (I use a cane) it was a nice retreat instead of the bustle of a hotel."

Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst

10/10 Excellent

"We had a great stay here for a long golf weekend with 10 guys. The house had plenty of room for our group, was comfortable to settle into, and made an excellent home base for playing courses in the area. It's conveniently located near several golf courses, grocery stores, and restaurants. We'd happily stay here again."

Find out more about Southern Pines

Everything you need to know about Southern Pines vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Pines vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Pines vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southern Pines vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Pines. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southern Pines in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $149 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southern Pines rentals

At Expedia, we put the best Southern Pines vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southern Pines rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Pines vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Pines. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Southern Pines?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Southern Pines, or you can select a secluded option if you want a relaxing place to 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 vacation home rentals in Southern Pines?

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8: Visitors like this Southern Pines vacation home rental. It is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Southern Pines is Beautiful 1920's Craftsman-Downtown Southern Pines.

How many vacation rentals are there in Southern Pines?

With 85 Expedia vacation rentals, you're sure 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 Hyland Hills Golf Club and Southern Pines Golf Club.

What are vacation rentals like in Southern Pines?

Vacation rentals are private accommodations you can stay in for a couple days or more in Southern Pines. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.

Southern Pines Vacation Rentals

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Check prices for these dates

Our top choices for Southern Pines vacation rentals

1. Cottage on Ridge- Short & Extended Stays

2. Charming Downtown Cottage

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

4. Walkable Cottage, Pet Friendly with Fenced Patio

5. The Cottage at Knollwood Manor

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

7. Beautiful 1920's Craftsman-Downtown Southern Pines

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

9. 11 E Pinehurst Manor

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

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

12. The Lucky Lie - Entire Condo in Pinehurst

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

14. 19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3

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

16. The McCaskill Cottage in the Village of Pinehurst!

17. 5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

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

19. Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8

20. Bourbon & Bubbles with Speakeasy & Hot Tub in Downtown Southern Pines!

Find vacation rentals that suit your style

Top Southern Pines Hotel Reviews

Holiday Inn Express Hotel & Suites Southern Pines by IHG

Find out more about Southern Pines

Explore a world of travel with Expedia

Frequently asked questions

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