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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Southern Pines vacation homes

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 CA $104
CA $231 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 CA $130
CA $250 total
includes taxes & fees
Oct 27 - Oct 28
Walkable Cottage, Pet Friendly with Fenced Patio
A two-story house with a white exterior, a brick chimney, and a covered porch.

3. 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 $277 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.

4. 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 CA $101
CA $400 total
includes taxes & fees
Nov 2 - Nov 3
Isle of the Pines, 1 mile from The Village of Pinehurst!
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

5. 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 CA $95
CA $339 total
includes taxes & fees
Oct 27 - Oct 28
The McCaskill Cottage in the Village of Pinehurst!
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

6. 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 CA $157
CA $652 total
includes taxes & fees
Nov 9 - Nov 10
The Mulligan!
Living area

7. 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 CA $151
CA $362 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

8. 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 $176
CA $435 total
includes taxes & fees
Nov 4 - Nov 5
Beautiful 1920's Craftsman-Downtown Southern Pines
A covered outdoor patio with a fire pit, seating area, and a grill.

9. 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 CA $138
CA $533 total
includes taxes & fees
Oct 28 - Oct 29
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
A modern living room with a white sofa, a wooden coffee table, and a blue rug.

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 $191
CA $556 total
includes taxes & fees
Nov 2 - Nov 3
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

11. Polo & Pine Retreat

Polo & Pine Retreat
Pinehurst
10.0 out of 10, Exceptional, (1 review)
"The property was clean and looked exactly like the pictures. It was a great value and we enjoyed our stay."
United States
kevin t.
The price is CA $97
CA $530 total
includes taxes & fees
Nov 2 - Nov 3
Polo & Pine Retreat
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

12. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (61 reviews)
"Cutest little house!"
United States
Aletta W.
The price is CA $188
CA $418 total
includes taxes & fees
Nov 2 - Nov 3
Charming Downtown Cottage
A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

13. Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn

Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Pinehurst
8.8 out of 10, Excellent, (18 reviews)
"Clean, space looked just like the description. Great location "
United States
Eli J.
The price is CA $138
CA $323 total
includes taxes & fees
Oct 27 - Oct 28
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

14. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (101 reviews)
"good value for the cost. needed to be cleaner."
United States
Erik W.
The price is CA $166
CA $658 total
includes taxes & fees
Oct 27 - Oct 28
NEW! Pinehurst Eight Sleeps 10!
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

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 $234
CA $611 total
includes taxes & fees
Oct 27 - Oct 28
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A modern kitchen with a central island, stainless steel appliances, and large windows.

16. The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (23 reviews)
"Great stay. Very pleased with the amenities of the house, the cleanliness and condition. Will plan to book here again next time we are coming to Southern Pines!"
United States
Michael M.
The price is CA $271
CA $702 total
includes taxes & fees
Nov 4 - Nov 5
The Cowboy
A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

17. Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst

Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
Taylortown
9.0 out of 10, Wonderful, (4 reviews)
"Really pretty place. The loft was very very small. I’m 5’4” and had to bend at the waist to get to the bed. Wish the front door had a way to cover it (full see through glass). The beds and couch were very comfortable. House was clean and decorated very nicely. Bathroom is a dream!!"
United States
Matthew C.
The price is CA $144
CA $226 total
includes taxes & fees
Nov 4 - Nov 5
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

18. Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace

Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace
Pinehurst
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay! The house was very comfortable, clean, and exactly as advertised. The beds were terrific—some of the best we’ve slept on while traveling.The host was gracious, extremely responsive, and a real pleasure to deal with from start to finish. Everything was easy and stress-free.Highly recommend this property. We would definitely stay here again!"
United States
Jake B.
The price is CA $247
CA $806 total
includes taxes & fees
Oct 27 - Oct 28
Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace
A hallway with a dark door, a hanging plant with lemons, a patterned rug, a table with a lamp, and a wall-mounted mirror.

19. Cheerful Eclectic Pinehurst Home! Less than 2 miles from Pinehurst #1-4

Cheerful Eclectic Pinehurst Home! Less than 2 miles from Pinehurst #1-4
Pinehurst
10.0 out of 10, Exceptional, (2 reviews)
"convenient location!"
United States
Elsa F.
The price is CA $195
CA $490 total
includes taxes & fees
Oct 27 - Oct 28
Cheerful Eclectic Pinehurst Home! Less than 2 miles from Pinehurst #1-4
A spacious living area with a wooden coffee table, a sofa, and a dining table. There is a green-framed window and a wall-mounted artwork.

20. Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!

Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Pinehurst
10.0 out of 10, Exceptional, (52 reviews)
"2nd time staying here, convenient location, would stay here again"
United States
Angela D.
The price is CA $202
CA $485 total
includes taxes & fees
Oct 28 - Oct 29
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
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

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

10/10 Excellent
"Room was clean staff friendly & helpful and price for Room fantastic will go again."
James 2-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Find out more about Southern Pines

Southern Pines Vacation Homes information

Number of reviews
581
Accommodation
274 Vacation Homes
Lowest Price
CA $226
Highest Price
CA $806

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