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The Cowboy

Vacation home in Southern Pines with kitchen

Photo gallery for The Cowboy

Living area
Living area
Living area
Living area
Private kitchen

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

Explore the area

View in a map
Southern Pines, NC
  • Place, Weymouth Woods-Sandhills Nature Preserve
    ‪10 min walk‬
  • Place, Sunrise Theater
    ‪15 min walk‬
  • Place, Hyland Hills Golf Club
    ‪2 min drive‬
  • Airport, Fayetteville, NC (FAY-Fayetteville Regional)
    ‪57 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Double Beds

3 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Shower only · Shampoo · Hair dryer

Spaces

Kitchen

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!
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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

About the neighborhood

Southern Pines

Southern Pines is home to this vacation 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 Hillcrest Park are also worth visiting.
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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
  • Pinehurst Resort - 11 min drive - 11.7 km

Getting around

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

Restaurants

  • ‪Southern Pines Brewing Company - ‬2 min drive
  • ‪Chapman's Food and Spirits - ‬13 min walk
  • ‪Betsy's Crepes - ‬16 min walk
  • ‪Hatchet Brewing Compan - ‬3 min drive
  • ‪Busaba Cafe - ‬19 min walk

Frequently asked questions

Is The Cowboy pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Cowboy?

As of Dec 25, 2025, prices found for a 1-night stay for 2 adults at The Cowboy on Jan 6, 2026 start from $403.33, 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.

What time is check-in at The Cowboy?

Check-in begins at 4:00 PM.

What time is check-out at The Cowboy?

Check-out is at 11:00 AM.

Where is The Cowboy located?

Situated in Southern Pines, this vacation 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 mi (2 km). Southern Pines Station is 15 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 12 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

TERESA D.

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

10/10 Excellent

Sam G.

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

About the host

Hosted by Ameeta Swaby

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