Southern Pines Vacation Home Rentals from CA $93: Search Top Private Vacation Homes for Rent

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

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Our top choices for Southern Pines vacation homes

A rustic wooden cabin with a black door, a window with colorful mugs, and a welcome mat on the deck.

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

Southern Pines

Ted D.

CA $215 total

includes taxes & fees

Sep 13 - Sep 14

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

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

Southern Pines

Gaynell B.

CA $284 total

includes taxes & fees

Sep 10 - Sep 11

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

3. Walkable Cottage, Pet Friendly with Fenced Patio

West Southern Pines

Katrina M.

CA $228 total

includes taxes & fees

Sep 8 - Sep 9

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

4. Beautiful 1920's Craftsman-Downtown Southern Pines

Southern Pines

Sean M.

CA $432 total

includes taxes & fees

Sep 20 - Sep 21

A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

5. Charming Downtown Cottage

Southern Pines

Jennifer G.

CA $415 total

includes taxes & fees

Sep 9 - Sep 10

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

6. The McCaskill Cottage in the Village of Pinehurst!

Old Town Pinehurst

Timothy

CA $344 total

includes taxes & fees

Sep 14 - Sep 15

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

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

Pinehurst

Jeremy

CA $382 total

includes taxes & fees

Sep 8 - Sep 9

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

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

Southern Pines

Michelle B.

CA $574 total

includes taxes & fees

Sep 8 - Sep 9

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

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

Downtown Southern Pines

Evan M.

CA $598 total

includes taxes & fees

Sep 28 - Sep 29

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

10. The Cowboy

Southern Pines

Michael M.

CA $672 total

includes taxes & fees

Sep 14 - Sep 15

A modern interior with a dark wall, a wooden ceiling, a tan leather sofa with colorful cushions, and a window with a view.

11. 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.

CA $400 total

includes taxes & fees

Sep 8 - Sep 9

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

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

Pinehurst

Mike S.

CA $465 total

includes taxes & fees

Sep 9 - Sep 10

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

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

Pinehurst

John M.

CA $467 total

includes taxes & fees

Sep 8 - Sep 9

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

14. The Mulligan!

Pinehurst

James N.

CA $617 total

includes taxes & fees

Sep 8 - Sep 9

A modern kitchen with white cabinets, a granite countertop, and three grey bar stools.

15. Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!

Pine Hurst

Randy F.

CA $647 total

includes taxes & fees

Sep 21 - Sep 22

A spacious living room with a blue sofa, a dining area with a wooden table, and a kitchen with modern appliances.

16. A Home in One ⛳️ Sleeps 10 & 🎱 Table!

West End

Billy P.

CA $638 total

includes taxes & fees

Sep 20 - Sep 21

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

17. NEW! Pinehurst Eight Sleeps 10!

Pine Hurst

CA $642 total

includes taxes & fees

Sep 14 - Sep 15

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

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

Pinehurst

Eli J.

CA $321 total

includes taxes & fees

Sep 8 - Sep 9

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

19. Polo & Pine Retreat

Pinehurst

kevin t.

CA $536 total

includes taxes & fees

Sep 21 - Sep 22

A living room with a fireplace, a flat-screen TV mounted above it, a round coffee table with a bowl, and a sofa.

20. Putt in the Pines 3BD 2 BA Charming Quiet Home

Aberdeen

Kirsten L.

CA $514 total

includes taxes & fees

Sep 8 - Sep 9

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Top Southern Pines Hotel Reviews

Residence Inn by Marriott Southern Pines/Pinehurst NC

10/10 Excellent

"Great location close to Pinehurst and Southern Pines shopping and restaurants."

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

10/10 Excellent

"Woven 2026 - Lighthouse Nation What a beautiful and peaceful place to gather for our Leadership Women’s Retreat! We are so grateful for the opportunity to step away, slow down, fellowship, laugh, pray, and simply enjoy time together. This beautiful setting was the perfect backdrop for making memories and strengthening the bonds we share as sisters in Christ. We left refreshed, encouraged, and so thankful for the time God gave us together. What a blessing! "

SoPi Cottage - Walk to Town - King Bed

10/10 Excellent

"House location was only a few blocks from townVery pet friendly nice fenced in back yardvery cleanIf you are going in fall or spring great fire pit with wood on siteWe will be coming in for music events off and on and will for sure stay here againCheck in was easy and owners had great communication"

19th Hole - Pickelball, Park, Walk to Downtown

10/10 Excellent

"We had an incredible stay! Our group ranged from seniors all the way down to a toddler and a baby, and the house was truly perfect for everyone. It was absolutely spotless, incredibly comfortable, and had every amenity we could possibly ask for. You can tell so much thought went into making the home welcoming and convenient for guests of all ages.The location was fantastic as well—so convenient and perfect for everything we wanted to do during our stay. We honestly couldn’t have asked for a better experience and would absolutely stay here again. Highly recommend!"

Find out more about Southern Pines

Southern Pines Vacation Homes information

Number of reviews	4,280
Accommodation	277 Vacation Homes
Lowest Price	CA $93
Highest Price	CA $286

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southern Pines vacation homes

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

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

3. Walkable Cottage, Pet Friendly with Fenced Patio