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 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.
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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
Aaron Sheppard Lakeside
Seagrove
Live Music
Aaron Sheppard Lakeside will perform live from 5-9 PM.
El Tequileño Tequila
Seagrove
Food & Drink
An event celebrating the rich heritage of El Tequileño Tequila will be held at Old Florida Fish House. Attendees can experience a curated dinner paired with tequila selections, guided by Master Distiller Antonio Salles. The event will take place on October 25th at 6:00 PM at Old Florida Fish House, located at 33 Heron’s Watch Way, Santa Rosa Beach, FL 32459. This unforgettable dining experience will blend authentic flavors with premium tequila pairings in a warm coastal setting. The price is $135++ per person. The event is hosted by Antonio Salles, Master Distiller of El Tequileño.
Dueling Pianos on the Main Stage
Seagrove
Live Music
Dueling Pianos can be seen on the Main Stage live from 7:30 to 10:30 p.m.
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten performs Lakeside live from 5-9 PM.
Jake and Aime Main Stage
Seagrove
Live Music
Jake and Aime will be performing live on the Main Stage from 6-9 PM.
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten Lakeside will be performing live from 5-9 PM.
Piano Tunes with Tim Buie Main Stage
Seagrove
Live Music
Tim Buie plays piano tunes on the Main Stage live from 6-9 PM.
Ryan Keefe Lakeside
Seagrove
Live Music
Ryan Keefe will be performing lakeside live from 5-9 PM.
Alex Napier on the Main Stage
Seagrove
Live Music
Alex Napier will be performing live on the Main Stage from 7-10 PM.
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten Lakeside will be performing live from 5-9 PM.
Alex Napier on the Main Stage
Seagrove
Live Music
Alex Napier will perform on the Main Stage live from 7-10 PM.
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten will be performing live from 5-9 PM at Lakeside.
Dueling Pianos on the Main Stage
Seagrove
Live Music
Dueling Pianos can be seen on the Main Stage live from 7-10 PM.
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten will be performing live from 5-9 PM at Lakeside.
Dueling Pianos on the Main Stage
Seagrove
Live Music
Dueling Pianos can be seen live on the Main Stage from 7:30 to 10:30 PM.
Sat, October 25
Aaron Sheppard Lakeside
Seagrove
Live Music
Aaron Sheppard Lakeside will perform live from 5-9 PM.
Sat, October 25
El Tequileño Tequila
Seagrove
Food & Drink
An event celebrating the rich heritage of El Tequileño Tequila will be held at Old Florida Fish House. Attendees can experience a curated dinner paired with tequila selections, guided by Master Distiller Antonio Salles. The event will take place on October 25th at 6:00 PM at Old Florida Fish House, located at 33 Heron’s Watch Way, Santa Rosa Beach, FL 32459. This unforgettable dining experience will blend authentic flavors with premium tequila pairings in a warm coastal setting. The price is $135++ per person. The event is hosted by Antonio Salles, Master Distiller of El Tequileño.
Sat, October 25
Dueling Pianos on the Main Stage
Seagrove
Live Music
Dueling Pianos can be seen on the Main Stage live from 7:30 to 10:30 p.m.
Sun, October 26
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten performs Lakeside live from 5-9 PM.
Sun, October 26
Jake and Aime Main Stage
Seagrove
Live Music
Jake and Aime will be performing live on the Main Stage from 6-9 PM.
Mon, October 27
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten Lakeside will be performing live from 5-9 PM.
Mon, October 27
Piano Tunes with Tim Buie Main Stage
Seagrove
Live Music
Tim Buie plays piano tunes on the Main Stage live from 6-9 PM.
Tue, October 28
Ryan Keefe Lakeside
Seagrove
Live Music
Ryan Keefe will be performing lakeside live from 5-9 PM.
Tue, October 28
Alex Napier on the Main Stage
Seagrove
Live Music
Alex Napier will be performing live on the Main Stage from 7-10 PM.
Wed, October 29
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten Lakeside will be performing live from 5-9 PM.
Wed, October 29
Alex Napier on the Main Stage
Seagrove
Live Music
Alex Napier will perform on the Main Stage live from 7-10 PM.
Thu, October 30
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten will be performing live from 5-9 PM at Lakeside.
Thu, October 30
Dueling Pianos on the Main Stage
Seagrove
Live Music
Dueling Pianos can be seen on the Main Stage live from 7-10 PM.
Fri, October 31
Russ Whitten Lakeside
Seagrove
Live Music
Russ Whitten will be performing live from 5-9 PM at Lakeside.
Fri, October 31
Dueling Pianos on the Main Stage
Seagrove
Live Music
Dueling Pianos can be seen live on the Main Stage from 7:30 to 10:30 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