Southern Pines Holiday House Rentals from AU$219: Search Holiday Homes

Southern Pines Holiday Homes
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Our top choices for Southern Pines holiday homes

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

A dining area with a round wooden table, two grey upholstered chairs, and a potted plant.

A living room with a blue sofa, two cushions, a small table with plants, and a framed picture on the wall.

A modern room with a wooden desk, a mounted TV, a small plant, and a decorative golden animal figure.

1. Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays

Southern Pines

9.8 out of 10, Exceptional, (50 reviews)

9.8/10

Exceptional

(50 reviews)

"Convenient, clean...a really cute place to stay."

Jeffrey S.

The price is AU$250

AU$250

includes taxes & fees

21 Oct - 22 Oct

Cottage on Ridge- Short & Extended Stays

A single-story house with a gray exterior, white trim, and a front porch.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A neatly made bed with patterned pillows and a green bedspread.

A living room with two beige armchairs, a round coffee table, and a TV stand with books and decorative items.

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)

9.8/10

Exceptional

(16 reviews)

"Perfect little place to stay with our dog! Would stay again."

Katrina M.

The price is AU$258

AU$258

includes taxes & fees

18 Oct - 19 Oct

Walkable Cottage, Pet Friendly with Fenced Patio

A two-story house with a white exterior, a brick chimney, and a covered porch.

A two-story building with a brick entrance, a small porch, and an American flag.

A wooden staircase with a view of a window and a door.

A modern living room with a grey sofa, wooden coffee table, and a TV on a black stand.

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)

10/10

Exceptional

(48 reviews)

"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"

Gaynell B.

The price is AU$305

AU$305

includes taxes & fees

19 Oct - 20 Oct

Upstairs at the Estate - Across from SP Golf Club

A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

A modern kitchen with wooden cabinets, a dining area with chairs, a leather sofa, and a large plant.

A living room with a sofa, ottoman, and chairs, a wooden coffee table, and a large window with blinds.

4. 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)

10/10

Exceptional

(22 reviews)

"Great location, updated interior, great overall experience"

Timothy

The price is AU$367

AU$367

includes taxes & fees

2 Nov - 3 Nov

The McCaskill Cottage in the Village of Pinehurst!

A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

A house with a front porch, a bench, a welcome mat, and a potted plant.

A bedroom with two beds, a ceiling fan, and a wall-mounted light fixture.

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a microwave. There is a dining area with a yellow sofa and a black armchair.

5. 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)

10/10

Exceptional

(37 reviews)

"Amazing place!"

Jeremy

The price is AU$435

AU$435

includes taxes & fees

19 Oct - 20 Oct

Isle of the Pines, 1 mile from The Village of Pinehurst!

A patio with a table and chairs, a small building with a door and window, and a white picket fence.

A house with a white picket fence, surrounded by trees and a well-maintained lawn.

A neatly made bed with a quilted bedspread and several pillows, flanked by bedside tables with lamps and clocks.

A dining area with a white brick fireplace, wooden chairs, a table, and a hanging light fixture.

6. Charming Downtown Cottage

Charming Downtown Cottage

Southern Pines

9.8 out of 10, Exceptional, (60 reviews)

9.8/10

Exceptional

(60 reviews)

"Cutest little house!"

Aletta W.

The price is AU$423

AU$423

includes taxes & fees

18 Oct - 19 Oct

Charming Downtown Cottage

A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with stools.

A living room with a beige sofa, a coffee table, and a ceiling fan.

A modern kitchen with wooden flooring, a central island with stools, a microwave, and a dishwasher.

7. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines

Southern Pines

10.0 out of 10, Exceptional, (99 reviews)

10/10

Exceptional

(99 reviews)

"Great location and was a perfect place to stay for a golf trip"

Sean M.

The price is AU$441

AU$441

includes taxes & fees

27 Oct - 28 Oct

Beautiful 1920's Craftsman-Downtown Southern Pines

A spacious living room with a fireplace, a dining area, and a view of the outdoors.

A covered patio with a round table and chairs, a grill, and a sliding glass door leading to an outdoor seating area.

A bedroom with a dark blue headboard, white bedding, two bedside tables with lamps, and a view of the outdoors through a window.

A modern kitchen with white cabinets, a round dining table with blue chairs, and a hanging blue pendant light.

8. The Mulligan!

The Mulligan!

Pinehurst

9.8 out of 10, Exceptional, (42 reviews)

9.8/10

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."

James N.

The price is AU$674

AU$674

includes taxes & fees

18 Oct - 19 Oct

The Mulligan!

A modern kitchen with white cabinets, a marble countertop, and a built-in oven.

A round table with a glass bowl of pinecones, surrounded by chairs with woven placemats.

A kitchen with white cabinetry, a granite countertop, a stainless steel sink, and a gold-framed mirror.

9. 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)

9.0/10

Wonderful

(18 reviews)

"Enjoyed our time here!"

Scot W.

The price is AU$391

AU$391

includes taxes & fees

16 Oct - 17 Oct

Beautiful 1 Bed Condo on Pinehurst Course No.5!

A living room with a wooden dining table, blue chairs, a sofa, and a television on the wall.

A covered outdoor area with a grill, two chairs, and a wooden railing.

A living room with a wooden coffee table, blue sofas, and a patterned rug.

A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a framed picture of North Carolina on the wall.

10. Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.

Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.

West Southern Pines

9.0 out of 10, Wonderful, (18 reviews)

9.0/10

Wonderful

(18 reviews)

"Everything was perfect. We enjoyed our stay! "

Brandon S.

Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

A modern living room with a dark brown sofa, a white sofa, and a beige sofa, all arranged around a central coffee table.

A two-story house with a front porch, a covered entryway, and a landscaped front yard.

A bedroom with a wooden headboard, a ceiling fan, and a large bed with white bedding.

11. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!

Pine Hurst

9.4 out of 10, Exceptional, (100 reviews)

9.4/10

Exceptional

(100 reviews)

"good value for the cost. needed to be cleaner."

Erik W.

The price is AU$706

AU$706

includes taxes & fees

28 Oct - 29 Oct

NEW! Pinehurst Eight Sleeps 10!

A modern living room with a white sofa, a wooden coffee table, and a blue rug.

A modern living room with a fireplace, wooden flooring, a flat-screen TV, and a kitchen in the background.

A wooden deck with a railing, surrounded by trees.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with two brown bar stools.

12. 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)

9.8/10

Exceptional

(32 reviews)

"It was perfect, beds extremely comfortable and safe location "

Shane H.

The price is AU$557

AU$557

includes taxes & fees

19 Oct - 20 Oct

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

A deck with a glass table and chairs overlooking a golf course.

A house with a number '210' on the door, a porch with steps, and a small garden area.

A golf course with pine trees, a pond, and a sign indicating a hole number.

A spacious living room with a high ceiling, a ceiling fan, a dining area with wooden furniture, and a large window offering a view of the outdoors.

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

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

Pinehurst

10.0 out of 10, Exceptional, (66 reviews)

10/10

Exceptional

(66 reviews)

"Perfect for our golf trip. Loved it and will be back."

John M.

The price is AU$510

AU$510

includes taxes & fees

18 Oct - 19 Oct

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

A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

A living room with a sofa, a coffee table, a bookshelf, and a kitchen area in the background.

A cabin with a porch, surrounded by tall pine trees and a wooden fence.

A living room with a fireplace, a television, and a sofa.

14. Polo & Pine Retreat

Polo & Pine Retreat

Pinehurst

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The property was clean and looked exactly like the pictures. It was a great value and we enjoyed our stay."

kevin t.

The price is AU$550

AU$550

includes taxes & fees

3 Nov - 4 Nov

Polo & Pine Retreat

A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

A two-story house with a front porch, a small window, and a flag.

A living room with a blue sofa, beige armchairs, a wooden coffee table, and a TV on a stand.

A hallway with wooden flooring, white walls, and a door leading to a room with a chair and a small table with a plant.

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, (12 reviews)

9.8/10

Exceptional

(12 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!"

Michelle B.

The price is AU$602

AU$602

includes taxes & fees

21 Oct - 22 Oct

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

A covered outdoor patio with a fire pit, seating area, and a grill.

A neatly arranged bedroom with a large bed, two bedside tables with lamps, a window with curtains, and a mirror on the wall.

A wooden deck with a white railing, large windows, and an American flag.

A modern living room with a sectional sofa, a matching ottoman, and two side tables with lamps.

16. 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)

9.4/10

Exceptional

(19 reviews)

"Great place for a family or golf getaway! "

Mike S.

The price is AU$524

AU$524

includes taxes & fees

28 Oct - 29 Oct

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

A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

A dining area with a round wooden table, woven centerpiece, and white placemats.

A two-story building with a central staircase and a small balcony on each floor.

A spacious living room with a dining area, large windows, and a view of the city.

17. 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)

8.8/10

Excellent

(18 reviews)

"Clean, space looked just like the description. Great location "

Eli J.

The price is AU$360

AU$360

includes taxes & fees

4 Nov - 5 Nov

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

A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

A wooden deck with a bench, overlooking a residential area with houses and trees.

A modern kitchen with a marble island, a dining area with a brick fireplace, and a living room with a sofa and TV.

A two-story house with a front porch, large windows, and a well-maintained lawn.

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)

10/10

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!"

Jake B.

The price is AU$766

AU$766

includes taxes & fees

28 Oct - 29 Oct

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

A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

A covered outdoor seating area with wicker furniture, a glass table, and a view of the outdoors.

A wooden kitchen shelf with plates, bowls, and utensils.

19. 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)

9.0/10

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!!"

Matthew C.

The price is AU$219

AU$219

includes taxes & fees

27 Oct - 28 Oct

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

A modern kitchen with a central island, stainless steel appliances, and large windows.

A modern living room with a leather sofa, a coffee table, and a fireplace.

A modern kitchen with a wooden dining table, chairs, and a backsplash.

A two-story house with a covered porch, a front door, and two windows on the upper floor.

20. The Cowboy

The Cowboy

Southern Pines

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 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!"

Michael M.

The price is AU$839

AU$839

includes taxes & fees

17 Oct - 18 Oct

The Cowboy

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

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

10/10 Excellent

"I was pleasantly surprised and enjoyed my stay."

Julian 1-night trip

Posted 17 hours ago

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

Clarion Inn Southern Pines - Pinehurst

8/10 Good

"Room was clean and it was quite. The room did smell really strong of moth balls. I did let front desk know. They were very helpful to make me comfortable. Breakfast was good. Over all southern pines is peaceful and nice hidden treasure. Thank you ladies at front desk!"

Iris 1-night trip

Posted 3 days ago

Clarion Inn Southern Pines - Pinehurst