Entire home

The Cowboy

Photo gallery for The Cowboy

A modern kitchen with a central island, stainless steel appliances, and large windows. - The Cowboy (Southern Pines)
A modern living room with a leather sofa, a coffee table, and a fireplace. - The Cowboy (Southern Pines)
A bedroom with a large bed, dark wood paneling on the walls, two bedside tables with lamps, and a window with curtains. - The Cowboy (Southern Pines)
A two-story house with a covered porch, a front door, and two windows on the upper floor. - The Cowboy (Southern Pines)
A modern kitchen with a wooden dining table, chairs, and a backsplash. - The Cowboy (Southern Pines)
The Cowboy provides laundry facilities and more. Stay connected with in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning

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About this property

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!

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

  • Smoke-free property

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)

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  • Air-conditioning
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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

Pets not 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
On-site 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

About the area

Southern Pines is home to this holiday home. Hyland Hills Golf Club and Southern Pines Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Weymouth Woods-Sandhills Nature Preserve and Reservoir Park. Malcolm Blue Farm and World Golf Hall of Fame are also worth visiting. Visit our Southern Pines travel guide
View more Holiday homes in Southern Pines
Map
Southern Pines, NC

What's nearby

  • Weymouth Woods-Sandhills Nature Preserve
    10 min walk - 0.9 km
  • Sunrise Theater
    15 min walk - 1.3 km
  • Campbell House Galleries
    18 min walk - 1.5 km
  • Hyland Hills Golf Club
    2 min drive - 1.4 km
  • Pine Needles Golf Club
    3 min drive - 2.3 km

Getting around

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

Restaurants

  • Red’s Corner
    3 min drive
  • The Jefferson Inn
    15 min walk
  • The Bell Tree Tavern
    15 min walk
  • Betsy's Crepes
    16 min walk
  • Swank
    15 min walk

Frequently asked questions

Is The Cowboy pet-friendly?

No, pets are not allowed at this property.

What time is check-in at The Cowboy?

Check-in begins at 4:00 PM.

What time is check-out at The Cowboy?

Checkout is at 11:00 AM.

Where is The Cowboy located?

Situated in Southern Pines, this holiday home is within a 15-minute walk of Weymouth Woods-Sandhills Nature Preserve and Sunrise Theater. Campbell House Galleries and Hyland Hills Golf Club are also within 1 mile (2 km). Southern Pines Station is 15 minutes by foot.

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Reviews

The Cowboy Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 22 out of 23 reviews
Rating 8 - Good. 1 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

Reviews

Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Southern pines

Overall it was great
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property. Very clean and comfortable. It’s walking distance to downtown Southern Pines which is great for dinners and drinks. We will definitely be back.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

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

10/10 Excellent

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