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The Cowboy

Southern Pines vacation home with kitchen

Choose dates to view prices

Photo gallery for The Cowboy

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 two-story house with a covered porch, a front door, and two windows on the upper floor.
A modern kitchen with a wooden dining table, chairs, and a backsplash.
A bedroom with a large bed, dark wood paneling on the walls, two bedside tables with lamps, and a window with curtains.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

Explore the area

View in a map
Southern Pines, NC
  • Place, Sunrise Theater
    ‪15 min walk‬
  • Place, Campbell House Galleries
    ‪18 min walk‬
  • Place, Hyland Hills Golf Club
    ‪2 min drive‬
  • Airport, Fayetteville, NC (FAY-Fayetteville Regional)
    ‪52 min drive‬

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About the neighborhood

Southern Pines

In Southern Pines .Within a 15-minute walk of the vacation home, you'll find Weymouth Woods-Sandhills Nature Preserve and Sunrise Theater. Campbell House Galleries and Hyland Hills Golf Club are also within 2 miles (3 km).
View more Vacation Homes in Southern PinesOpens in a new window

What's nearby

  • Weymouth Woods-Sandhills Nature Preserve - 10 min walk - 0.6 miles
  • Sunrise Theater - 15 min walk - 0.8 miles
  • Campbell House Galleries - 18 min walk - 1.0 mile
  • Hyland Hills Golf Club - 2 min drive - 0.9 miles
  • Pine Needles Golf Club - 3 min drive - 1.5 miles

Getting around

  • Southern Pines Station - 15 min walk
  • Fayetteville Regional Airport (FAY) - 55 min drive

Restaurants

  • ‪Southern Pines Brewing Company - ‬2 min drive
  • ‪Red’s Corner - ‬3 min drive
  • ‪Hatchet Brewing Compan - ‬3 min drive
  • ‪Betsy's Crepes - ‬16 min walk
  • ‪Swank - ‬15 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

The Cowboy

Welcome to The Cowboy, hosted by Isle of the Pines Property Group – a striking home seamlessly blending modern-western decor in a prime location near downtown Southern Pines. This thoughtfully designed home offers a unique atmosphere, embodying a luxury cowboy vibe!

We pride ourselves on the inviting space we provide through offering luxury amenities such as a fully equipped kitchen, abundantly stocked coffee bar, toiletries upon arrival, several family oriented games, and so much more!

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Property amenities

Internet

  • Available in the house: WiFi

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Games

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited.

Frequently asked questions

How close is The Cowboy to the airport?

This vacation home is 40.2 mi (55-min drive) away from the Fayetteville Regional Airport (FAY) airport, the closest popular airport to the property.

How much does it cost to stay at The Cowboy?

As of Jul 26, 2026, prices found for a 1-night stay for 2 adults at The Cowboy on Aug 11, 2026 start from $532, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does The Cowboy have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does The Cowboy offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at The Cowboy?

No, there is no casino at this vacation home.

What time is check-in at The Cowboy?

Check-in begins at 4:00 PM.

Is there free parking at The Cowboy?

Free parking is not available at this vacation home.

Does The Cowboy have a pool?

This vacation home does not have a pool.

Does The Cowboy have a spa?

There are no spa services available at this vacation home.

How close is The Cowboy to downtown Southern Pines?

This vacation home is 0.6 mi away from Southern Pines.

The Cowboy Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Michael M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Sherry K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Cowboy is a wonderful place to stay. It’s fresh and clean, well equipped, beautifully decorated. Perfect for our group. We would definitely stay here again if the need arises.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Melissa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was lovely. The beds and linens were very comfortable and we all slept so well. The kids adored the game room and the host was incredibly communicative. We would love to stay again.
Stayed 5 nights in Apr 2026
Verified

10/10 Excellent

jorie f.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay here - the home is super clean and cozy. Well stocked kitchen and lots of space in the open concept 1st floor. Loved the back yard with fire pit and the kids especially loved the game room in the garage. Walkable to town, and all together would 100% stay here again when we come back!
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

Jayne Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect! Very clean, great layout with ample room, and loved the backyard amenities and game room! It made for a perfect get-away!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Jack V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home, amenities, and location are all fantastic. Thank you!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

A B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great experience!

Place was as advertised and host was easy to work with. Went on a golf trip and the location was amazing for several of our courses.
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Damond V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pinehurst Visit

Great visit / Excellent communication and the property was in top shape. Great experience +++
Stayed 1 night in Jun 2024
Verified

10/10 Excellent

John Michael H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Southern pines

Overall it was great
Stayed 6 nights in Jul 2025
Verified

10/10 Excellent

MONICA F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Cowboy was the most fun house I have ever stayed in. From check in to check out, our crew had a blast. The back yard fire pit and garage game room was a hit with the teenagers and the adults appreciated nice comfortable beds after a long day at the horse park. We had all of the amenities and more we wanted in a house and hope to come back and stay here again sometime!
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Greg A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome upscale property in Southern Pines. Beautiful kitchen and living area and big yard with fire pit and grill. The host couldn't of been more responsive or helpful. Highly recommend.
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

James B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice stay

We enjoyed our stay. Everything was nice and new. Very nice location. Easy to find and very well stocked. Would suggest this house for anyone planning to golf or just enjoy the area. Very clean and well managed. I give a 5 out of 5 only because 5 is the highest rating.
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Bruce T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Golf Getaway

The Cowboy worked well for 4 couples in Pinehurst for golf. Very well appointed. Our group loved spending nights in back around the firepit with that fun mural on the garage--felt like our own private bar. Location works. The common area downstairs could be a bit larger to accommodate all guests at once. Overall, highly recommend this property.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Kevin O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the perfect home for a golf weekend in Southern Pines. Great space for four people and close to downtown and the courses. Communication with the owners was as great as well.
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

TERESA D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Sam G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 1 night in Sep 2024

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