Description
House Rules
Amenities
Bed and Baths
Location
Community
Upcoming Events
Reviews
Host Family

Surfing Cowboy

Sleeps 8 - 3 Bedrooms - 3 Baths

57 Cassine Garden Circle, Santa Rosa Beach, FL 32459

📍

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

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.

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

Community

Seagrove - Diamond

Upcoming Events

Tue, January 6

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.

Wed, January 7

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.

Thu, January 8

Dueling Pianos

Seagrove

Live Music

The Dueling Pianos show can be seen live from 6:30 to 9:30 PM.

Fri, January 9

Dueling Pianos

Seagrove

Live Music

Dueling Pianos will be performing live from 7 PM to 10 PM.

Sat, January 10

Dueling Pianos

Seagrove

Live Music

Dueling Pianos is scheduled to perform live from 7 PM to 10 PM.

Sun, January 11

Bryan Umphy-Main Stage

Seagrove

Live Music

Bryan Umphy can be seen performing live on the Main Stage between 6 and 9 PM.

Mon, January 12

Bryan Umphy-Main Stage

Seagrove

Live Music

Bryan Umphy-Main Stage is scheduled to perform live from 6-9 PM.

Tue, January 13

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier is scheduled to perform live on the Main Stage from 6 PM to 9 PM.

Wed, January 14

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.

Thu, January 15

Dueling Pianos

Seagrove

Live Music

Dueling Pianos can be seen live from 6:30 to 9:30 PM.

Fri, January 16

30A Singer/Songwriter

Seagrove

Live Music

The 30A Singer/Songwriter event will feature a live performance from 7:00 PM to 10:00 PM.

Sat, January 17

30A Singer/Songwriter

Seagrove

Live Music

A 30A singer/songwriter will be performing live from 7 PM to 10 PM.

Sun, January 18

30A Singer/Songwriter

Seagrove

Live Music

The event features a 30A singer/songwriter performing live from 7 PM to 10 PM.

Mon, January 19

30A Singer/Songwriter

Seagrove

Live Music

A 30A Singer/Songwriter performance will be held live from 7 PM to 10 PM.

Tue, January 20

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.

Wed, January 21

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier is performing live on the Main Stage from 6 PM to 9 PM.

Thu, January 22

Dueling Pianos

Seagrove

Live Music

Dueling Pianos will perform live from 6:30 PM to 9:30 PM.

Fri, January 23

Dueling Pianos

Seagrove

Live Music

The Dueling Pianos show can be seen live from 7 PM to 10 PM.

Sat, January 24

Red Shoe Party

Seagrove

Arts & Culture

The Florida Fish House is set to host the Red Shoe Party on Saturday, January 24, 2026. This elegant cocktail-style event supports children in foster care across Okaloosa and Walton Counties. The event is inspired by the iconic red shoes, which symbolize hope, comfort, and belonging. Cocktail attire is encouraged, and guests can participate in the Red Shoe Contest categories: Sportiest, Most Glamorous, and Most Creative. The evening will feature chef-driven small plates, entree stations, desserts, themed cocktails, a silent auction, and meaningful stories highlighting the impact of the cause. Tickets are $150 and are of limited availability. Sponsorship opportunities are also available. More information and tickets can be found at the event's website.

Sat, January 24

Dueling Pianos

Seagrove

Live Music

Dueling Pianos will be performing live from 7 to 10 PM.

Sun, January 25

Russ Whiten-Main Stage

Seagrove

Live Music

The event features a live performance by Russ Whiten on the Main Stage, scheduled from 6 PM to 9 PM.

Tue, January 27

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier performs on the Main Stage live from 6:00 PM to 9:00 PM.

Wed, January 28

Alex Napier-Main Stage

Seagrove

Live Music

Alex Napier is scheduled to perform live on the Main Stage from 6 PM to 9 PM.

Thu, January 29

Dueling Pianos

Seagrove

Live Music

Dueling Pianos can be caught live from 6:30 to 9:30 PM.

Fri, January 30

Dueling Pianos

Seagrove

Live Music

Dueling Pianos will be performing live from 7:00 PM to 10:00 PM.

Sat, January 31

Dueling Pianos

Seagrove

Live Music

Dueling Pianos performs live from 7 PM to 10 PM.

Reviews - 18

nicole

Oct 2025

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!

ian

Loveland, OH

Sep 2025

Google

Love working with oversee and staying at the Surfing Cowboy. This is our 4th year and we can’t wait for next year!

amy

Mar 2025

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.

mary-elizabeth

Apr 2025

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!

amy

Mar 2025

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.

winnie

Hendersonville, TN

Oct 2024

Google

The house was clean and beautiful. A perfect location and had everything we needed and more! The communication from the host was amazing. We will definitely go back the the Surfin Cowboy!

bonnie

Jul 2024

Google

amanda

, TN

Oct 2024

Vrbo

shawn

Sep 2024

Airbnb

karen

Jul 2024

Airbnb

We had a wonderful stay at Surfin Cowboy. It was just like the pictures. I was clean and the location was great!

robert

Jun 2024

Airbnb

peggy

Pekin, IL

Jan 2023

Oversee

Loved the location…..house was perfect.

heather

Roswell

Sep 2023

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!

pia

Wildwood, MO

Mar 2023

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!

traci

Mar 2023

Airbnb

Wonderful place to stay

karen

Woodstock, IL

Feb 2023

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.

ryleigh

Jan 2023

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!

peggy

Pekin, IL

Jan 2023

Vrbo

Adorable house and close to the beach