Surfing Cowboy
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Surfing Cowboy
Surfin’ Cowboy by Oversee 30A | 2025 Diamond Winner-Best Rental Mgmt.
Surfin' Cowboy is a beautiful home, ideal for up to 8 guests craving coastal relaxation, 30A adventure, and the perfect Emerald Coast experience. The white picket fence adds a charming nuance.
📍 Cassine Village in Seagrove Beach
🏖️ .3 miles from One Seagrove Place Beach Access
😎 5-minute stroll to stunning coastal dune lake
👙 2 Community pools!
🛌 3 bedrooms, 3 baths
🚲 3 bikes!
🔥 Gas grill
🚿 Outdoor shower
🦞 4-star restaurants
This gorgeous 3-bedroom, 3-bath getaway, built in 2020, is just a short stroll from the sugar-white sands of Seagrove Beach. Eastern Lake is close, too, and a must-visit.
Tucked in tranquil Cassine Village, the white picket fence says, “We’re home!” You’ll have access to two pools, tennis courts, breathtaking nature trails(!), plus shops and restaurants just steps away.
On the main floor, the delightfully decorated, open living, dining, and kitchen area is designed for easy, breezy gatherings. The kitchen’s fully equipped for whipping up meals, with bar seating for three and a dining table for six.
The first-floor guest bedroom features a queen bed, a twin XL bunk, and a walk-in closet. Upstairs, the primary suite includes a queen bed, an en-suite bathroom with a soaking tub, dual vanity, and a private balcony.
The guest room has three twin XL beds and its own bathroom,
Colorful and inviting, the massive screened-in porch out back is a wonderful space and a favorite hangout spot. Enjoy the ping pong table, custom bar, and comfy seating— all framed by lush greenery for that extra dose of privacy.
The front porches on both levels are ideal for sipping coffee or unwinding in the fresh air. Outside, there’s space for three cars, an outdoor hot-and-cold shower, a gas grill, and a beach gear closet stocked with chairs.
Dining spots, a local seafood market, and shops are just a short walk away. Seaside is two miles down the road, perfect for a scenic bike ride. Check out The Big Chill for live entertainment and food, or take an easy pedal over to Deer Lake State Park to explore the untouched beauty of 30A’s beaches and rare dune lakes.
Seagrove Beach is in the middle of everything, making Surfin' Cowboy the ideal launchpad for exploring all of 30A’s vibrant communities. A truly magnificent home.
Overview:
- .3 miles from One Seagrove Place Beach Access
- 3 bedrooms, 3 baths
- 1500 sq ft
- 2 community pools
- 3 bikes included
- Gas grill
- Wi-Fi
- Table tennis
- Outdoor shower
- Bassinet available
Overnight:
FIRST FLOOR
- Guest room: Twin/queen built-in bunk, hall bath, TV
SECOND FLOOR
- Primary bedroom: Queen bed, private bath, private balcony, TV
- Bunk room: Twin/twin bunk, single twin bed, private bath, TV
Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.
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Take the 3D walkthrough.
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Hassle-free check-in.
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Add your trip dates to get the cancellation details for this stay.
House Rules
Who can stay.
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8 guests maximum
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No pets
What's allowed.
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Check-in after 4:00 PM
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Check-out before 10:00 AM
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No smoking
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No parties or events
Amenities
Community Amenities
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Community elevator
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Community pool
Outdoor
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Balcony
Entertainment
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Cable
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Smart TV
Indoor
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Wireless internet
Safety Features
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Carbon monoxide detector
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Fire extinguisher
Kitchen
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Standard coffee maker
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Microwave
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Refrigerator
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Toaster
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Dishwasher
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Stove
Bed And Bathroom
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Hair dryer
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Iron & board
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Bathtub
Complimentary Items
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3 Oversee bikes
Bed and Baths
1st Floor
bedroom
1 Bunk bed
full bathroom
2nd Floor
Primary Bedroom
1 Queen bed
full bathroom
bedroom
1 Bunk bed 1 Single bed
full bathroom
Location
Upcoming Events
David Martin on the Lawn
Seagrove Beach
Live Music
David Martin will be performing live on the Lawn from 5 to 9 PM.
Alex Napier Duo on the Main Stage
Seagrove Beach
Live Music
The Alex Napier Duo will perform live from 7 to 10 PM.
Brittnie Sloan
Seagrove Beach
Live Music
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Russ Whitten can be seen performing live from 5 to 9 PM.
Alex Napier Duo on the Main Stage
Seagrove Beach
Live Music
The Alex Napier Duo will perform live from 7 to 10 PM.
Sean Brewer
Seagrove Beach
Live Music
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Russ Whitten can be seen performing live from 5 to 9 PM.
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
Dueling Pianos will perform live from 7 to 10 PM.
Jay Lilies
Seagrove Beach
Live Music
This summer, individuals can enjoy live music, theater, and more under the shade of The Pavilion at Watersound Town Center. On Thursday, June 26th, the 30A Songwriters Showcase will feature Ruthie Foster. Each month, a different children's play from The Seaside REP will be presented, along with family nights or friendly neighborhood races with Fleet Feet. The 30A Songwriter’s Festival Showcase will include performances by nationally known artists such as the Abe Patridge Band, Ruthie Foster, Gurufish, and Livingston Taylor. With ample parking, a covered pavilion, and ceiling fans, the Pavilion at Watersound Town Center is quickly becoming a popular destination for outdoor events in South Walton. These events are free and open to the public.
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Thursday night has become Trivia Night at AJ's on the Bayou. The event begins at 6:30 PM and is free to participate in. There are numerous prizes from AJ's for the top teams. It promises to be an enjoyable evening on the Bayou with live trivia.
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
David Bly on the Lawn
Seagrove Beach
Live Music
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Alex Napier on the Main Stage
Seagrove Beach
Live Music
Tue, June 24
David Martin on the Lawn
Seagrove Beach
Live Music
David Martin will be performing live on the Lawn from 5 to 9 PM.
Tue, June 24
Alex Napier Duo on the Main Stage
Seagrove Beach
Live Music
The Alex Napier Duo will perform live from 7 to 10 PM.
Tue, June 24
Brittnie Sloan
Seagrove Beach
Live Music
Wed, June 25
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Russ Whitten can be seen performing live from 5 to 9 PM.
Wed, June 25
Alex Napier Duo on the Main Stage
Seagrove Beach
Live Music
The Alex Napier Duo will perform live from 7 to 10 PM.
Wed, June 25
Sean Brewer
Seagrove Beach
Live Music
Thu, June 26
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Russ Whitten can be seen performing live from 5 to 9 PM.
Thu, June 26
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
Dueling Pianos will perform live from 7 to 10 PM.
Fri, June 27
Jay Lilies
Seagrove Beach
Live Music
This summer, individuals can enjoy live music, theater, and more under the shade of The Pavilion at Watersound Town Center. On Thursday, June 26th, the 30A Songwriters Showcase will feature Ruthie Foster. Each month, a different children’s play from The Seaside REP will be presented, along with family nights or friendly neighborhood races with Fleet Feet. The 30A Songwriter’s Festival Showcase will include performances by nationally known artists such as the Abe Patridge Band, Ruthie Foster, Gurufish, and Livingston Taylor. With ample parking, a covered pavilion, and ceiling fans, the Pavilion at Watersound Town Center is quickly becoming a popular destination for outdoor events in South Walton. These events are free and open to the public.
Fri, June 27
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Thursday night has become Trivia Night at AJ’s on the Bayou. The event begins at 6:30 PM and is free to participate in. There are numerous prizes from AJ’s for the top teams. It promises to be an enjoyable evening on the Bayou with live trivia.
Fri, June 27
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
Sat, June 28
David Bly on the Lawn
Seagrove Beach
Live Music
Sat, June 28
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
Sun, June 29
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Sun, June 29
Dueling Pianos on the Main Stage
Seagrove Beach
Live Music
Mon, June 30
Russ Whitten on the Lawn
Seagrove Beach
Live Music
Mon, June 30
Alex Napier on the Main Stage
Seagrove Beach
Live Music
Reviews - 16
Google
We had an AMAZING time. What a great place to stay. Seriously we were so taken care of by you guys. Thanks for making it one of our favorite family vacations. I couldn’t say enough good things about all the communication, the house was immaculate and the area was so taken care of. Thank you! Bless you all.
Airbnb
Comfortable, well appointed, fresh, with plenty of lightweight beach gear like chairs, coolers, and umbrella provided.
Tennis courts, pools, bikes, and ping pong table gave us plenty to do off the beach!
Airbnb
We were so taken care of! Lots of clear communication from Oversee. They took the time to answer our questions. The house was amazing! We had the best week. I will 100% book a vacation home with Oversee in the future.
Google
Google
Vrbo
Airbnb
Airbnb
We had a wonderful stay at Surfin Cowboy. It was just like the pictures. I was clean and the location was great!
Airbnb
Oversee
Loved the location…..house was perfect.
Vrbo
We had an amazing experience at the Surfing Cowboy. It was exactly as described and the access to the beach was even better than I expected. The house was beautifully decorated and had all the kitchen appliances, cookware, cups, plates, serving platters, etc. The bikes provided were such an amazing asset to have. We don’t have one negative thing to say and can’t wait to stay again next year!! Thank you for your amazing hospitality!
Vrbo
We enjoyed our stay for Spring Break 2023. Great location, property was super clean. A little smaller than we envisioned but well equipped, well maintained house with nice amenities and super close to beach and main road. Great neighborhood. Nice extras like beach chairs and bikes. Great stay!
Airbnb
Wonderful place to stay
Vrbo
We greatly enjoyed our week at Surfing Cowboy. The home is gorgeous and the location couldn’t be better. The nature trail was a BIG surprise! The home is equipped with EVERYTHING to make your vacation complete.
Vrbo
This rental was everything we expected and more! The location is great, whether you are headed to the beach or cruising down 30A on a bike. We would definitely stay again!
Vrbo
Adorable house and close to the beach
Host Family
Diamond Office at Sunnyside
Office location:
Diamond Office at Sunnyside, Florida
Contact Diamond Office at Sunnyside
Surfing Cowboy
Santa Rosa Beach - Sleeps 8
3 bedrooms - 4 beds - 3 baths