Surfing Cowboy
Share
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 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 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.
-
Take the 3D walkthrough.
-
Hassle-free check-in.
-
Add your trip dates to get the cancellation details for this stay.
House Rules
Who can stay.
-
8 guests maximum
-
No pets
What's allowed.
-
Check-in after 4:00 PM
-
Check-out before 10:00 AM
-
No smoking
-
No parties or events
Amenities
Community Amenities
-
Community elevator
-
Community pool
Outdoor
-
Balcony
Entertainment
-
Cable
-
Smart TV
Indoor
-
Wireless internet
Safety Features
-
Carbon monoxide detector
-
Fire extinguisher
Kitchen
-
Standard coffee maker
-
Microwave
-
Refrigerator
-
Toaster
-
Dishwasher
-
Stove
Bed And Bathroom
-
Hair dryer
-
Iron & board
-
Bathtub
Complimentary Items
-
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
Alex Napier-Main Stage
Seagrove
Sports & Games
Alex Napier will be performing live on the Main Stage from 6:30 PM to 9:30 PM.
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.
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.
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage can be seen live from 7 PM to 10 PM.
Russ Whitten-Lakeside
Seagrove
Live Music
Russ Whitten-Lakeside will be performing live from 4:30 PM to 8:30 PM.
Dueling Pianos-Main Stage
Seagrove
Live Music
Gentiva Hospice hosts a monthly Grief and Loss Support Group open to anyone in the community who has experienced the loss of a family member or friend, regardless of whether they received hospice care. This supportive gathering offers a safe and compassionate environment for individuals to share, connect, and find comfort among others who understand their experience. The group meets on the second Thursday of each month from 3:00 PM to 4:30 PM at Gentiva Hospice, located at 732 Baldwin Ave, Suite A, DeFuniak Springs, FL 32435. For further details, individuals can contact Chaplain Thom Phillips by phone at 850-951-9849 or via email.
Brunch Buffet with Santa
Seagrove
Family Fun
A fun-filled evening awaits attendees at Beach Camp Brewpub's Trivia Night, starting at 6 PM. Guests are encouraged to bring their friends to test their knowledge while enjoying food, cold drinks, and great company. Whether someone is a trivia professional or simply looking for a few laughs, it offers a perfect way to spend a night by the beach.
Holiday Wine Market
Seagrove
Food & Drink
The Daytrader Tiki Bar & Restaurant announced the return of "Miracle at The Daytrader," celebrating its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, the pop-up will feature elaborate festive décor, whimsical holiday themes, and imaginative Christmas-themed cocktails at the 30A seaside location. The Miracle concept, which started in 2014 in New York City, has grown into a global tradition with over 200 locations worldwide, known for its dazzling decorations, cheerful atmosphere, and collectible holiday glassware. The Daytrader, recently named "Best Cocktail Spot on 30A" in the 2025 Hot Spot Awards and led by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical twist on the holidays. This year's menu includes new drinks like the Dancing Sugarplums and Miracle Mouse, alongside popular returning favorites such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive staples like Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase. From November 17 through December 31, visitors can enjoy a full Christmas experience at Miracle at The Daytrader, combining tiki culture with holiday kitsch. Guests can sip seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric decorations. The Daytrader is open daily from 11 AM to 9 PM and operates on a first-come, first-served basis. As part of its global mission, Miracle will once again donate 10% of all proceeds from select glassware sales (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a nonprofit dedicated to preventing blindness and restoring sight worldwide.
Russ Whitten-Lakeside
Seagrove
Live Music
Salt Rock Revival, a classic rock and jams duo, performed free live music brought by local artists.
Dueling Pianos-Main Stage
Seagrove
Live Music
The business hosts a monthly local’s weekend where locals and snowbirds receive a 20% discount on classes. This offer is available during the second Saturday and Sunday of every month. Interested participants are encouraged to call 850-231-0544 to reserve a class.
David Martin-Lakeside Brunch
Seagrove
Live Music
The Daytrader Tiki Bar & Restaurant announced the return of Miracle at The Daytrader, marking its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, Miracle at The Daytrader will feature elaborate festive décor, nostalgic holiday themes, and unique Christmas-themed cocktails at the popular seaside destination on 30A. The Miracle concept originated in 2014 in New York City and has since grown to over 200 locations globally, spanning the United States, Canada, Europe, Asia, and Central America. The pop-up is recognized worldwide for its spectacular decorations, playful holiday spirit, and collectible seasonal glassware. The Daytrader, recently honored with Best Cocktail Spot on 30A in the 2025 Hot Spot Awards and overseen by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical interpretation of the holidays. This year’s drink menu includes new creations like the Dancing Sugarplums and Miracle Mouse, alongside favorite returning cocktails such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive items like the Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase. From November 17 through December 31, both locals and visitors can visit Miracle at The Daytrader for a complete Christmas experience that merges tiki culture with holiday kitsch. Guests can enjoy seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric décor, offering a holiday blend unique to Miracle. The Daytrader operates daily from 11 AM to 9 PM, accommodating guests on a first-come, first-served basis. In line with its global mission, Miracle will again contribute 10% of the proceeds from sales of specific glassware (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a non-profit organization dedicated to preventing blindness and restoring sight globally.
Russ-Main Stage
Seagrove
Live Music
The event features Russ performing live on the Main Stage from 6 to 9 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier can be seen live on the Main Stage from 6:30 PM to 9:30 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier will be performing live on the Main Stage from 6:30 PM to 9:30 PM.
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.
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage is scheduled to perform live between 7 PM and 10 PM.
Mon, December 8
Alex Napier-Main Stage
Seagrove
Sports & Games
Alex Napier will be performing live on the Main Stage from 6:30 PM to 9:30 PM.
Tue, December 9
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, December 10
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, December 11
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage can be seen live from 7 PM to 10 PM.
Fri, December 12
Russ Whitten-Lakeside
Seagrove
Live Music
Russ Whitten-Lakeside will be performing live from 4:30 PM to 8:30 PM.
Fri, December 12
Dueling Pianos-Main Stage
Seagrove
Live Music
Gentiva Hospice hosts a monthly Grief and Loss Support Group open to anyone in the community who has experienced the loss of a family member or friend, regardless of whether they received hospice care. This supportive gathering offers a safe and compassionate environment for individuals to share, connect, and find comfort among others who understand their experience. The group meets on the second Thursday of each month from 3:00 PM to 4:30 PM at Gentiva Hospice, located at 732 Baldwin Ave, Suite A, DeFuniak Springs, FL 32435. For further details, individuals can contact Chaplain Thom Phillips by phone at 850-951-9849 or via email.
Sat, December 13
Brunch Buffet with Santa
Seagrove
Family Fun
A fun-filled evening awaits attendees at Beach Camp Brewpub’s Trivia Night, starting at 6 PM. Guests are encouraged to bring their friends to test their knowledge while enjoying food, cold drinks, and great company. Whether someone is a trivia professional or simply looking for a few laughs, it offers a perfect way to spend a night by the beach.
Sat, December 13
Holiday Wine Market
Seagrove
Food & Drink
The Daytrader Tiki Bar & Restaurant announced the return of “Miracle at The Daytrader,” celebrating its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, the pop-up will feature elaborate festive décor, whimsical holiday themes, and imaginative Christmas-themed cocktails at the 30A seaside location.
The Miracle concept, which started in 2014 in New York City, has grown into a global tradition with over 200 locations worldwide, known for its dazzling decorations, cheerful atmosphere, and collectible holiday glassware. The Daytrader, recently named “Best Cocktail Spot on 30A” in the 2025 Hot Spot Awards and led by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical twist on the holidays. This year’s menu includes new drinks like the Dancing Sugarplums and Miracle Mouse, alongside popular returning favorites such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive staples like Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase.
From November 17 through December 31, visitors can enjoy a full Christmas experience at Miracle at The Daytrader, combining tiki culture with holiday kitsch. Guests can sip seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric decorations. The Daytrader is open daily from 11 AM to 9 PM and operates on a first-come, first-served basis.
As part of its global mission, Miracle will once again donate 10% of all proceeds from select glassware sales (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a nonprofit dedicated to preventing blindness and restoring sight worldwide.
Sat, December 13
Russ Whitten-Lakeside
Seagrove
Live Music
Salt Rock Revival, a classic rock and jams duo, performed free live music brought by local artists.
Sat, December 13
Dueling Pianos-Main Stage
Seagrove
Live Music
The business hosts a monthly local’s weekend where locals and snowbirds receive a 20% discount on classes. This offer is available during the second Saturday and Sunday of every month. Interested participants are encouraged to call 850-231-0544 to reserve a class.
Sun, December 14
David Martin-Lakeside Brunch
Seagrove
Live Music
The Daytrader Tiki Bar & Restaurant announced the return of Miracle at The Daytrader, marking its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, Miracle at The Daytrader will feature elaborate festive décor, nostalgic holiday themes, and unique Christmas-themed cocktails at the popular seaside destination on 30A.
The Miracle concept originated in 2014 in New York City and has since grown to over 200 locations globally, spanning the United States, Canada, Europe, Asia, and Central America. The pop-up is recognized worldwide for its spectacular decorations, playful holiday spirit, and collectible seasonal glassware.
The Daytrader, recently honored with Best Cocktail Spot on 30A in the 2025 Hot Spot Awards and overseen by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical interpretation of the holidays. This year’s drink menu includes new creations like the Dancing Sugarplums and Miracle Mouse, alongside favorite returning cocktails such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive items like the Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase.
From November 17 through December 31, both locals and visitors can visit Miracle at The Daytrader for a complete Christmas experience that merges tiki culture with holiday kitsch. Guests can enjoy seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric décor, offering a holiday blend unique to Miracle. The Daytrader operates daily from 11 AM to 9 PM, accommodating guests on a first-come, first-served basis.
In line with its global mission, Miracle will again contribute 10% of the proceeds from sales of specific glassware (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a non-profit organization dedicated to preventing blindness and restoring sight globally.
Sun, December 14
Russ-Main Stage
Seagrove
Live Music
The event features Russ performing live on the Main Stage from 6 to 9 PM.
Mon, December 15
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier can be seen live on the Main Stage from 6:30 PM to 9:30 PM.
Tue, December 16
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier will be performing live on the Main Stage from 6:30 PM to 9:30 PM.
Wed, December 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.
Thu, December 18
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage is scheduled to perform live between 7 PM and 10 PM.
Reviews - 18
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!
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