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The Cowboy

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Photo gallery for The Cowboy

Private kitchen
4 bedrooms, iron/ironing board, WiFi, bed sheets
Living area
Exterior
Dining

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, 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

Room options

About the neighborhood

Southern Pines

This vacation home is a short stroll from Weymouth Woods-Sandhills Nature Preserve and Sunrise Theater. The vacation home includes conveniences like a kitchen.
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
  • Southern Pines Golf Club - 3 min drive - 1.7 miles

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
  • ‪Busaba Cafe - ‬19 min walk
  • ‪Betsy's Crepes - ‬16 min walk
  • ‪Hatchet Brewing Compan - ‬3 min drive

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!
The vacation home is air-conditioned and features a kitchen and 3 bathrooms, and there's space to spread out with 4 bedrooms. Other standard amenities include a washing machine and an ironing board.

Similar properties

Dining
Residence Inn by Marriott Southern Pines/Pinehurst NC
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  • Pool
  • Hot tub
  • Breakfast included
  • Pet friendly
9.0 out of 10, Wonderful, 368 reviews
$120 nightly
The price is $136
May 31 - Jun 1
Total with taxes and fees
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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
Minimum check-in age: 18

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 18

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Frequently asked questions

What's there to do within easy reach of this vacation home?

This vacation home is located in Southern Pines, a short 10-minute walk from Weymouth Woods-Sandhills Nature Preserve and also 14 minutes on foot from Sunrise Theater. You'll also find Southern Pines Golf Club and Pine Needles Golf Club within a short drive.

How much does it cost to stay at The Cowboy?

As of Apr 30, 2026, prices found for a 1-night stay for 2 adults at The Cowboy on May 4, 2026 start from $465, 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.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

The Cowboy Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 15 out of 15 reviews
Rating 8 - Good. 0 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Melissa C.

Liked: Cleanliness
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

10/10 Excellent

Sherry K.

Liked: Cleanliness
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

10/10 Excellent

Michael M.

Liked: Cleanliness
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

10/10 Excellent

jorie f.

Liked: Cleanliness
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

MONICA F.

Liked: Cleanliness
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

Jack V.

Liked: Cleanliness
The home, amenities, and location are all fantastic. Thank you!
Stayed 3 nights in Sep 2025

10/10 Excellent

Greg A., Washington, D.C.

Liked: Cleanliness
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

Jayne Q.

Liked: Cleanliness
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

John Michael H.

Liked: Cleanliness

Southern pines

Overall it was great
Stayed 6 nights in Jul 2025

10/10 Excellent

TERESA D.

Liked: Cleanliness
Stayed 3 nights in Apr 2025

10/10 Excellent

A B.

Liked: Cleanliness

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

Sam G.

Liked: Cleanliness
Stayed 1 night in Sep 2024

10/10 Excellent

Bruce T.

Liked: Cleanliness

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

James B.

Liked: Cleanliness

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

Damond V.

Liked: Cleanliness

Pinehurst Visit

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