Surfing Cowboy
Surfing Cowboy
Surfing Cowboy
Surfing Cowboy
Surfin’ Cowboy by Oversee 30A | Perfect in Walton County Awards – Three-Time Diamond Winner – Best Rental Mgmt. 2026, 2025, 2024
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.
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 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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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
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen performing live from 7 PM to 10 PM.
Dueling Pianos
Seagrove
Live Music
They can catch Dueling Pianos live from 7 to 10 PM.
Valentine's Dinner Specials
Seagrove
Food & Drink
The event is scheduled to begin at 4:30 PM on February 14th.
Valentine's Day
Seagrove
Food & Drink
The restaurant is encouraging guests to make their reservations and select their preferred location for Valentine’s Day. The chefs have prepared special menus for the holiday celebration.
Dueling Pianos
Seagrove
Live Music
The event features Dueling Pianos performing live from 7 PM to 10 PM.
Brunch by the Lake
Seagrove
Food & Drink
The establishment offers a Sunday Brunch every Sunday, beginning at 10 am.
Russ Whitten-Main Stage
Seagrove
Live Music
Russ Whitten performs live from 7-10 PM.
Presidents’ Day
Seagrove
Family Fun
It was Presidents' Day.
Russell Brand Show
Seagrove
Arts & Culture
The Russell Brand Show is scheduled for February 16th and 17th at 5:30 PM. Tickets are available for purchase on their website.
Mahjong
Seagrove
Sports & Games
The Mahjong event is held on select Tuesdays from 11:30 a.m. to 4:30 p.m., specifically on the 3rd, 17th, and 24th of the month, and offers participants the opportunity to learn and play the game.
Russell Brand Show
Seagrove
Arts & Culture
Tickets for the Russel Brand Show on February 16th and 17th at 5:30pm are available for purchase on the website.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6:30 PM to 9:30 PM.
Ash Wednesday
Seagrove
Arts & Culture
Ash Wednesday is scheduled for 2026.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier-Main Stage performs live from 6:30 to 9:30 PM.
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is held every Thursday from 11:30 am to 1:30 pm on the 5th, 12th, 19th, and 26th.
Dueling Pianos
Seagrove
Live Music
A live Dueling Pianos performance is scheduled from 7:00 PM to 10:00 PM.
Coastside Wine Tasting with John Gibson (Salexis Wines)
Seagrove
Food & Drink
Coastside Wine Tasting with John Gibson (Salexis Wines) is scheduled to take place. Additionally, AJ’s Grayton Beach will host a job fair on February 2nd and February 9th from 12 PM – 5 PM. Applicants interested in positions such as Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers are encouraged to bring their resume and attend ready to interview. Candidates will have the opportunity to meet with hiring managers from the locally owned and operated restaurant group, which has been part of the community for over 42 years, to discuss the various opportunities available across all departments.
Dueling Pianos
Seagrove
Live Music
AJ’s Grayton Beach is holding a job fair on February 2nd and February 9th from 12 PM to 5 PM. The restaurant group is seeking applicants for various departments, including Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers. Interested candidates should attend the event prepared for an interview and bring their resume to meet face-to-face with hiring managers. Additionally, the venue features Dueling Pianos live from 7 PM to 10 PM. The locally owned and operated restaurant group has been serving the community for over 42 years.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen live from 7 PM to 10 PM.
Brunch by the Lake
Seagrove
Food & Drink
Sunday Brunch is available every Sunday starting at 10 a.m.
Russ Whitten-Main Stage
Seagrove
Food & Drink
Russ Whitten can be caught live from 7 p.m. to 10 p.m.
Mahjong
Seagrove
Food & Drink
Alex Napier-Main Stage
Seagrove
Live Music
The Freeport State of the City Breakfast, sponsored by Ascension Sacred Heart Hospital on the Emerald Coast, is a special edition of the Quarterly Wake Up Walton Breakfast. This informative event is scheduled for February 3rd at 7:30 a.m. at the E.O. Wilson Biophilia Center in Freeport. The breakfast will gather business leaders, community members, and local stakeholders to hear important updates on the future of the city. Mayor Russ Barley will deliver the State of the City of Freeport Address, sharing insights on current initiatives, economic development, and the future outlook for the community. Attendees will have the opportunity to enjoy breakfast while networking with fellow professionals and gaining valuable perspective on the growth and direction of Freeport. The event will cost $20 for members and $35 for non-members. Additionally, Alex Napier will be performing live on the Main Stage from 6:30 p.m. to 9:30 p.m.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6:30 PM to 9:30 PM.
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is scheduled to take place every Thursday from 11:30 AM to 1:30 PM. The dates for these events are the 5th, 12th, 19th, and 26th.
Thu, February 12
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen performing live from 7 PM to 10 PM.
Fri, February 13
Dueling Pianos
Seagrove
Live Music
They can catch Dueling Pianos live from 7 to 10 PM.
Sat, February 14
Valentine's Dinner Specials
Seagrove
Food & Drink
The event is scheduled to begin at 4:30 PM on February 14th.
Sat, February 14
Valentine's Day
Seagrove
Food & Drink
The restaurant is encouraging guests to make their reservations and select their preferred location for Valentine’s Day. The chefs have prepared special menus for the holiday celebration.
Sat, February 14
Dueling Pianos
Seagrove
Live Music
The event features Dueling Pianos performing live from 7 PM to 10 PM.
Sun, February 15
Brunch by the Lake
Seagrove
Food & Drink
The establishment offers a Sunday Brunch every Sunday, beginning at 10 am.
Sun, February 15
Russ Whitten-Main Stage
Seagrove
Live Music
Russ Whitten performs live from 7-10 PM.
Mon, February 16
Presidents’ Day
Seagrove
Family Fun
It was Presidents’ Day.
Mon, February 16
Russell Brand Show
Seagrove
Arts & Culture
The Russell Brand Show is scheduled for February 16th and 17th at 5:30 PM. Tickets are available for purchase on their website.
Tue, February 17
Mahjong
Seagrove
Sports & Games
The Mahjong event is held on select Tuesdays from 11:30 a.m. to 4:30 p.m., specifically on the 3rd, 17th, and 24th of the month, and offers participants the opportunity to learn and play the game.
Tue, February 17
Russell Brand Show
Seagrove
Arts & Culture
Tickets for the Russel Brand Show on February 16th and 17th at 5:30pm are available for purchase on the website.
Tue, February 17
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6:30 PM to 9:30 PM.
Wed, February 18
Ash Wednesday
Seagrove
Arts & Culture
Ash Wednesday is scheduled for 2026.
Wed, February 18
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier-Main Stage performs live from 6:30 to 9:30 PM.
Thu, February 19
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is held every Thursday from 11:30 am to 1:30 pm on the 5th, 12th, 19th, and 26th.
Thu, February 19
Dueling Pianos
Seagrove
Live Music
A live Dueling Pianos performance is scheduled from 7:00 PM to 10:00 PM.
Fri, February 20
Coastside Wine Tasting with John Gibson (Salexis Wines)
Seagrove
Food & Drink
Coastside Wine Tasting with John Gibson (Salexis Wines) is scheduled to take place. Additionally, AJ’s Grayton Beach will host a job fair on February 2nd and February 9th from 12 PM – 5 PM. Applicants interested in positions such as Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers are encouraged to bring their resume and attend ready to interview. Candidates will have the opportunity to meet with hiring managers from the locally owned and operated restaurant group, which has been part of the community for over 42 years, to discuss the various opportunities available across all departments.
Fri, February 20
Dueling Pianos
Seagrove
Live Music
AJ’s Grayton Beach is holding a job fair on February 2nd and February 9th from 12 PM to 5 PM. The restaurant group is seeking applicants for various departments, including Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers. Interested candidates should attend the event prepared for an interview and bring their resume to meet face-to-face with hiring managers. Additionally, the venue features Dueling Pianos live from 7 PM to 10 PM. The locally owned and operated restaurant group has been serving the community for over 42 years.
Sat, February 21
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen live from 7 PM to 10 PM.
Sun, February 22
Brunch by the Lake
Seagrove
Food & Drink
Sunday Brunch is available every Sunday starting at 10 a.m.
Sun, February 22
Russ Whitten-Main Stage
Seagrove
Food & Drink
Russ Whitten can be caught live from 7 p.m. to 10 p.m.
Tue, February 24
Mahjong
Seagrove
Food & Drink
Tue, February 24
Alex Napier-Main Stage
Seagrove
Live Music
The Freeport State of the City Breakfast, sponsored by Ascension Sacred Heart Hospital on the Emerald Coast, is a special edition of the Quarterly Wake Up Walton Breakfast. This informative event is scheduled for February 3rd at 7:30 a.m. at the E.O. Wilson Biophilia Center in Freeport. The breakfast will gather business leaders, community members, and local stakeholders to hear important updates on the future of the city. Mayor Russ Barley will deliver the State of the City of Freeport Address, sharing insights on current initiatives, economic development, and the future outlook for the community. Attendees will have the opportunity to enjoy breakfast while networking with fellow professionals and gaining valuable perspective on the growth and direction of Freeport. The event will cost $20 for members and $35 for non-members. Additionally, Alex Napier will be performing live on the Main Stage from 6:30 p.m. to 9:30 p.m.
Wed, February 25
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6:30 PM to 9:30 PM.
Thu, February 26
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is scheduled to take place every Thursday from 11:30 AM to 1:30 PM. The dates for these events are the 5th, 12th, 19th, and 26th.
Reviews - 24
Airbnb
This house was perfection. Already thinking about when we can go back. Love the porches, ping pong table, walkability to beach and restaurants. Beautifully decorated and comfortable. Cutest neighborhood with pool, tennis courts and bikes to ride around.
Airbnb
We have no complaints whatsoever. The property was as listed and exceeded our expectations.
Google
The Surfin’ Cowboy exceeded our expectations. The house is well appointed, beautiful, and a close walk/bike ride to the beach. My family loved having the bikes to ride and the ping pong table to play. The bedding is super comfortable and amenities were a nice added touch. We would most definitely come back!
Google
Love working with oversee and staying at the Surfing Cowboy. This is our 4th year and we can’t wait for next year!
Airbnb
Vrbo
The house was perfect for our group! Very clean, great location, well stocked— great attention to detail. Having the bikes, golf cart baggo ping pong and games was a hit for the adults and kids. Service was awesome- timely responses. We would stay again!
Airbnb
Great house with a short walk to the beach and restaurants.
Airbnb
We enjoyed our stay here. It was a nice size for 7guests. Beautiful home and good location, walking distance to beach although the access was closed so we had to drive. We were left with no paper towels and only 2 trash bags. Not sure if this is normal or just an accident so I‚’d bring some if you plan on staying here. Overall still loved our stay here there was just a few little things to improve on. Would definitely book again!
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
Prices include all fees and taxes