Surfing Cowboy

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.

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  • Hassle-free check-in.
  • Add your trip dates to get the cancellation details for this stay.

House Rules

Who can stay.

  • Guests Maximum8 guests maximum
  • No petsNo pets

What's allowed.

  • Check-inCheck-in after 4:00 PM
  • Check-outCheck-out before 10:00 AM
  • No smokingNo smoking
  • No parties or eventsNo parties or events

Amenities

Community Amenities

  • Community elevatorCommunity elevator
  • Community poolCommunity pool

Outdoor

  • BalconyBalcony

Entertainment

  • CableCable
  • Smart TVSmart TV

Indoor

  • Wireless internetWireless internet

Safety Features

  • Carbon monoxide detectorCarbon monoxide detector
  • Fire extinguisherFire extinguisher

Kitchen

  • Standard coffee makerStandard coffee maker
  • MicrowaveMicrowave
  • RefrigeratorRefrigerator
  • ToasterToaster
  • DishwasherDishwasher
  • StoveStove

Bed And Bathroom

  • Hair dryerHair dryer
  • Iron & boardIron & board
  • BathtubBathtub

Complimentary Items

  • 3 Oversee bikes3 Oversee bikes
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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

Thu, January 29

Dueling Pianos

Seagrove
Live Music Live Music

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

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Fri, January 30

Dueling Pianos

Seagrove
Live Music Live Music

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

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Sat, January 31

Dueling Pianos

Seagrove
Live Music Live Music

Dueling Pianos performs live from 7 PM to 10 PM.

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Sun, February 1

Brunch by the Lake

Seagrove
Food & Drink Food & Drink

The establishment offers a Sunday Brunch every Sunday, beginning at 10 am.

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Sun, February 1

Dueling Pianos

Seagrove
Live Music Live Music

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

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Mon, February 2

Groundhog Day

Seagrove
Arts & Culture Arts & Culture

It was Groundhog Day.

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Tue, February 3

Mahjong

Seagrove
Sports & Games Sports & Games

Participants can learn and play Mahjong on select Tuesdays from 11:30 am to 4:30 pm. These dates include the 3rd, 17th, and 24th of the month.

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Tue, February 3

Alex Napier-Main Stage

Seagrove
Live Music Live Music

Alex Napier can be caught live on the Main Stage from 6–9 PM.

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Wed, February 4

Alex Napier-Main Stage

Seagrove
Live Music Live Music

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

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Thu, February 5

Beach Mahjong

Seagrove
Sports & Games Sports & Games

Beach Mahjong takes place every Thursday from 11:30 a.m. to 1:30 p.m. The dates for the event are the 5th, 12th, 19th, and 26th.

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Thu, February 5

Dueling Pianos

Seagrove
Live Music Live Music

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

Learn More
Fri, February 6

Dueling Pianos

Seagrove
Live Music Live Music

The venue hosts a live Dueling Pianos event, which takes place from 7:00 PM to 10:00 PM.

Learn More
Sat, February 7

Dueling Pianos

Seagrove
Live Music Live Music

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

Learn More
Sun, February 8

Brunch by the Lake

Seagrove
Food & Drink Food & Drink

A Sunday brunch commences every Sunday at 10 a.m.

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Sun, February 8

Football Party

Seagrove
Sports & Games Sports & Games

An announcement was made inviting people to a football party celebrating the Super Bowl.

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Sun, February 8

Football Party

Seagrove
Sports & Games Sports & Games

An announcement was made inviting people to a football party celebrating the Super Bowl.

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Tue, February 10

Alex Napier-Main Stage

Seagrove
Live Music Live Music

Alex Napier performs live on the Main Stage from 6:30 PM to 9:30 PM.

Learn More
Wed, February 11

Alex Napier-Main Stage

Seagrove
Live Music Live Music

Alex Napier performs on the Main Stage live from 6:30 PM to 9:30 PM.

Learn More
Thu, February 12

Beach Mahjong

Seagrove
Sports & Games Sports & Games

Beach Mahjong is scheduled for every Thursday from 11:30 a.m. to 1:30 p.m. The dates for the event are the 5th, 12th, 19th, and 26th.

Learn More
Thu, February 12

Dueling Pianos

Seagrove
Live Music Live Music

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

Learn More
Fri, February 13

Dueling Pianos

Seagrove
Live Music Live Music

They can catch Dueling Pianos live from 7 to 10 PM.

Learn More
Sat, February 14

Valentine's Dinner Specials

Seagrove
Food & Drink Food & Drink

The event is scheduled to begin at 4:30 PM on February 14th.

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Sat, February 14

Dueling Pianos

Seagrove
Live Music Live Music

The event features Dueling Pianos performing live from 7 PM to 10 PM.

Learn More
Sun, February 15

Brunch by the Lake

Seagrove
Food & Drink Food & Drink

The establishment offers a Sunday Brunch every Sunday, beginning at 10 am.

Learn More
Sun, February 15

Russ Whitten-Main Stage

Seagrove
Live Music Live Music

Russ Whitten performs live from 7-10 PM.

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Mon, February 16

Presidents’ Day

Seagrove
Family Fun Family Fun

It was Presidents' Day.

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Mon, February 16

Russell Brand Show

Seagrove
Arts & Culture 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.

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Tue, February 17

Mahjong

Seagrove
Sports & Games 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.

Learn More
Tue, February 17

Russell Brand Show

Seagrove
Arts & Culture Arts & Culture

Tickets for the Russel Brand Show on February 16th and 17th at 5:30pm are available for purchase on the website.

Learn More
Tue, February 17

Alex Napier-Main Stage

Seagrove
Live Music Live Music

Alex Napier is scheduled to perform live on the Main Stage from 6:30 PM to 9:30 PM.

Learn More
Wed, February 18

Ash Wednesday

Seagrove
Arts & Culture Arts & Culture

Ash Wednesday is scheduled for 2026.

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Wed, February 18

Alex Napier-Main Stage

Seagrove
Live Music Live Music

Alex Napier-Main Stage performs live from 6:30 to 9:30 PM.

Learn More
Thu, February 19

Beach Mahjong

Seagrove
Sports & Games Sports & Games

Beach Mahjong is held every Thursday from 11:30 am to 1:30 pm on the 5th, 12th, 19th, and 26th.

Learn More

Reviews - 24

sarah
Oct 2025 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.

nicole
Oct 2025 Airbnb

We have no complaints whatsoever. The property was as listed and exceeded our expectations.

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!

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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!

jordan
Aug 2025 Airbnb
kim
Little Rock, AR
Jun 2025 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!

david
May 2025 Airbnb

Great house with a short walk to the beach and restaurants.

emilee
Apr 2025 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!

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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.

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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!
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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!

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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!

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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

Host Family

Diamond Office at Sunnyside

Joseph Hunter
Haylee Becktel
Mackenzie Matthews
Roy Foreman
Meagan Wood
The Diamond Office is just a short hop from our homes between Seagrove and Watersound, making it easy for us to handle requests with speed and care.

Office location:

Diamond Office at Sunnyside, Florida

Contact Diamond Office at Sunnyside
Price Tag Prices include all fees and taxes
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1 guest