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

Southern Pines Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Southern Pines vacation rentals

A modern living room with a wooden floor, a leopard print rug, a white console table with a lamp, and a large plant.

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 ￥12,863
￥27,248 total
includes taxes & fees
Oct 28 - Oct 29
Cottage on Ridge- Short & Extended Stays
A single-story house with a gray exterior, white trim, and a front porch.

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 ￥14,546
￥27,961 total
includes taxes & fees
Oct 25 - Oct 26
Walkable Cottage, Pet Friendly with Fenced Patio
A bedroom with a bed, a desk, a chair, a ceiling fan, and a view through a glass door.

3. 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 ￥10,658
￥25,326 total
includes taxes & fees
Oct 27 - Oct 28
Located in # 6 golf community, close to First Health Moore Regional Hospital.
A modern kitchen with a double sink, a coffee maker, and a variety of snacks on the counter.

4. 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, (56 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
The price is ￥14,294
￥33,332 total
includes taxes & fees
Oct 25 - Oct 26
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
A modern bedroom with a bed, a desk, and a balcony with a chair.

5. 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 ￥14,106
￥40,026 total
includes taxes & fees
Oct 27 - Oct 28
The Lucky Lie - Entire Condo in Pinehurst
A house with a front porch, steps leading to a green door, and a welcome mat.

6. The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
9.8 out of 10, Exceptional, (20 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 Cottage at Knollwood Manor
A two-story house with a white exterior, a brick chimney, and a covered porch.

7. 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 ￥14,106
￥32,384 total
includes taxes & fees
Oct 27 - Oct 28
Upstairs at the Estate - Across from SP Golf Club
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

8. 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)
"Amazing place!"
United States
Jeremy
The price is ￥11,894
￥45,350 total
includes taxes & fees
Nov 2 - Nov 3
Isle of the Pines, 1 mile from The Village of Pinehurst!
A living room with a sofa, armchair, coffee table, and a view through a glass door to the outside.

9. Studio Seven at Pine Valley

Studio Seven at Pine Valley
Pinehurst
9.6 out of 10, Exceptional, (14 reviews)
"Great stay"
United States
Lauren
The price is ￥6,946
￥29,121 total
includes taxes & fees
Nov 9 - Nov 10
Studio Seven at Pine Valley
A dining area with a poker table, chairs, a hanging light fixture, and a view of the outside through large windows.

10. 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 ￥12,836
￥51,873 total
includes taxes & fees
Oct 27 - Oct 28
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

11. 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, (22 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is ￥10,495
￥38,780 total
includes taxes & fees
Oct 27 - Oct 28
The McCaskill Cottage in the Village of Pinehurst!
A modern kitchen with a white island, yellow bar stools, stainless steel appliances, and large windows with curtains.

12. 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 ￥14,889
￥40,734 total
includes taxes & fees
Oct 25 - Oct 26
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
A modern kitchen with a dining area, a flat-screen TV, and a coffee maker.

13. 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, (95 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 ￥14,294
￥33,508 total
includes taxes & fees
Oct 26 - Oct 27
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
Living area

14. Beautiful 1 Bed Condo on Pinehurst Course No.5!

Beautiful 1 Bed Condo on Pinehurst Course No.5!
Pinehurst
9.0 out of 10, Wonderful, (18 reviews)
"Enjoyed our time here!"
United States
Scot W.
The price is ￥16,927
￥40,559 total
includes taxes & fees
Oct 25 - Oct 26
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

15. Cozy Pinehurst 2BR Apartment w/3 Beds • Across from Pinehurst #6 • Firepit

Cozy Pinehurst 2BR Apartment w/3 Beds • Across from Pinehurst #6 • Firepit
Pinehurst
10.0 out of 10, Exceptional, (13 reviews)
"Great stay!"
United States
Amanda B.
The price is ￥11,849
￥45,447 total
includes taxes & fees
Oct 28 - Oct 29
Cozy Pinehurst 2BR Apartment w/3 Beds • Across from Pinehurst #6 • Firepit
A dining area with a wooden table and chairs, a hanging light fixture, and wall-mounted artwork.

16. 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)
"We loved our stay. The condo was perfect and very close to Pinehurst. We would stay there again!"
United States
Candice J.
The price is ￥14,106
￥41,266 total
includes taxes & fees
Oct 26 - Oct 27
The Mulligan Manor - 1BR/1BA Condo in Pinehurst
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

17. The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (42 reviews)
"Great location to get to all of the golf courses we played. Plenty of room for the 6 of us. Host very attentive."
United States
James N.
The price is ￥18,450
￥74,157 total
includes taxes & fees
Oct 27 - Oct 28
The Mulligan!
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a large window with a view of the outside.

18. 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 ￥16,786
￥44,827 total
includes taxes & fees
Oct 27 - Oct 28
The Perfect Lie in Pinehurst! A golfer's paradise!
A corner room with a desk, chair, and large windows with blinds.

19. 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 ￥14,889
￥34,251 total
includes taxes & fees
Oct 25 - Oct 26
11 E Pinehurst Manor
A covered outdoor patio with a fire pit, seating area, and a grill.

20. Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf

Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
Pinehurst
9.4 out of 10, Exceptional, (19 reviews)
"Great place for a family or golf getaway! "
United States
Mike S.
The price is ￥15,482
￥55,219 total
includes taxes & fees
Oct 28 - Oct 29
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
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

SoPi Cottage - Walk to Town - King Bed

SoPi Cottage - Walk to Town - King Bed

10/10 Excellent
"Second time at the property. Absolutely perfect"
jet t. 7-night trip
Posted 1 day ago
SoPi Cottage - Walk to Town - King Bed

Find out more about Southern Pines

Search for holiday rentals in Southern Pines on Expedia! You can easily find your home rentals, villas, holiday apartments in Southern Pines using one of the methods below:

  • View our selection of featured holiday rentals in Southern Pines
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  • Enter your travel dates to view the best deals on holiday rentals in Southern Pines while they last

Look no further and take a look at our great range of rental properties in Southern Pines!

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.