Surfing Cowboy

Sleeps 8 - 3 Bedrooms - 3 Baths
57 Cassine Garden Circle, Santa Rosa Beach, FL 32459

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 Place 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 Place 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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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

Wed, June 4

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Wed, June 4

Alex Napier Duo on the Main Stage

Seagrove Beach
Live Music Live Music

The Alex Napier Duo will perform live from 7 to 10 PM.

Learn More
Thu, June 5

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Thu, June 5

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

Dueling Pianos will perform live from 7 to 10 PM.

Learn More
Fri, June 6

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Fri, June 6

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

The audience can enjoy a live performance by Dueling Pianos from 7:30 to 10:30 PM.

Learn More
Sat, June 7

Aaron Shepard on the Lawn

Seagrove Beach
Live Music Live Music

Aaron Shepard will be performing live on the Lawn from 5 to 9 PM.

Learn More
Sat, June 7

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

The audience can enjoy a live performance by Dueling Pianos from 7:30 to 10:30 PM.

Learn More
Sun, June 8

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Sun, June 8

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

Dueling Pianos will perform live from 7 to 10 PM.

Learn More
Mon, June 9

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Mon, June 9

Alex Napier on the Main Stage

Seagrove Beach
Food & Drink Food & Drink

Alex Napier can be seen performing live from 7 to 10 PM.

Learn More
Tue, June 10

David Martin on the Lawn

Seagrove Beach
Live Music Live Music

David Martin will be performing live on the Lawn from 5 to 9 PM.

Learn More
Tue, June 10

Alex Napier Duo on the Main Stage

Seagrove Beach
Live Music Live Music

The Alex Napier Duo will perform live from 7 to 10 PM.

Learn More
Wed, June 11

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Wed, June 11

Alex Napier Duo on the Main Stage

Seagrove Beach
Live Music Live Music

The Alex Napier Duo will perform live from 7 to 10 PM.

Learn More
Thu, June 12

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Thu, June 12

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

Dueling Pianos will perform live from 7 to 10 PM.

Learn More
Fri, June 13

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Fri, June 13

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

The audience can enjoy a live performance by Dueling Pianos from 7:30 to 10:30 PM.

Learn More
Sat, June 14

Aaron Shepard on the Lawn

Seagrove Beach
Live Music Live Music

Aaron Shepard will be performing live on the Lawn from 5 to 9 PM.

Learn More
Sat, June 14

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

The audience can enjoy a live performance by Dueling Pianos from 7:30 to 10:30 PM.

Learn More
Sun, June 15

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Sun, June 15

Dueling Pianos on the Main Stage

Seagrove Beach
Live Music Live Music

Dueling Pianos will perform live from 7 to 10 PM.

Learn More
Mon, June 16

Russ Whitten on the Lawn

Seagrove Beach
Live Music Live Music

Russ Whitten can be seen performing live from 5 to 9 PM.

Learn More
Mon, June 16

Alex Napier on the Main Stage

Seagrove Beach
Live Music Live Music

Alex Napier can be seen performing live from 7 to 10 PM.

Learn More

Reviews - 16

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
Roy Foreman
Chris Parsons
Mackenzie Matthews
Haylee Becktel
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
Guests

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