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Southern Pines Vacation Rentals

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Our top choices for Southern Pines vacation 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 CA $90
CA $206 total
includes taxes & fees
Nov 8 - Nov 9
Cottage on Ridge- Short & Extended Stays

2. 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 CA $130
CA $237 total
includes taxes & fees
Nov 10 - Nov 11
Walkable Cottage, Pet Friendly with Fenced Patio

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 CA $126
CA $352 total
includes taxes & fees
Dec 2 - Dec 3
The Lucky Lie - Entire Condo in Pinehurst

4. 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 CA $133
CA $361 total
includes taxes & fees
Nov 10 - Nov 11
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

5. 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 CA $134
CA $291 total
includes taxes & fees
Nov 8 - Nov 9
The Cottage at Knollwood Manor

6. 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 CA $95
CA $214 total
includes taxes & fees
Nov 15 - Nov 16
Located in # 6 golf community, close to First Health Moore Regional Hospital.

7. 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 CA $189
CA $403 total
includes taxes & fees
Nov 8 - Nov 9
Charming Downtown Cottage

8. 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 CA $183
CA $440 total
includes taxes & fees
Nov 15 - Nov 16
NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn

9. 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 CA $188
CA $531 total
includes taxes & fees
Nov 10 - Nov 11
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

10. 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.
The price is CA $201
CA $547 total
includes taxes & fees
Nov 8 - Nov 9
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!

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, (82 reviews)
"Great location"
United States
Launi M.
The price is CA $141
CA $370 total
includes taxes & fees
Nov 17 - Nov 18
The Perfect Lie in Pinehurst! A golfer's paradise!

12. 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 CA $120
CA $265 total
includes taxes & fees
Nov 8 - Nov 9
Upstairs at the Estate - Across from SP Golf Club

13. 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 CA $186
CA $427 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful 1920's Craftsman-Downtown Southern Pines

14. 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 CA $101
CA $531 total
includes taxes & fees
Nov 10 - Nov 11
Isle of the Pines, 1 mile from The Village of Pinehurst!

15. 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 CA $233
CA $587 total
includes taxes & fees
Nov 9 - Nov 10
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines

16. Lakeside Condo on Pinehurst #5

Lakeside Condo on Pinehurst #5
Pinehurst
10.0 out of 10, Exceptional, (65 reviews)
"We loved this spot. Great location and great host! Highly recommend"
United States
Mitchell L.
The price is CA $164
CA $415 total
includes taxes & fees
Nov 17 - Nov 18
Lakeside Condo on Pinehurst #5

17. 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 CA $128
CA $282 total
includes taxes & fees
Nov 10 - Nov 11
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

18. 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 CA $281
CA $687 total
includes taxes & fees
Nov 8 - Nov 9
The Cowboy

19. 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 price is CA $229
CA $393 total
includes taxes & fees
Nov 9 - Nov 10
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst

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.
The price is CA $255
CA $538 total
includes taxes & fees
Nov 20 - Nov 21
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Simulator & Unbeatable Golf Experience On 2 Acres!: Visitors like this Southern Pines vacation home rental. It offers a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 vacation rentals are there in Southern Pines?

With 88 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 Mid Pines Golf Club and Pine Needles 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.