Surfing Cowboy

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

Surfin’ Cowboy by Oversee 30A | 2024 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

Sat, December 21

Ryan Keef – Lakeside

Seagrove
Live Music Live Music

Ryan Keef can be seen performing live from 5 to 9 PM.

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Sat, December 21

Dueling Piano – Main Stage

Seagrove
Live Music Live Music

Dueling Piano can be enjoyed live from 7 to 10 PM.

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Sun, December 22

Alex Napier – Main Stage

Seagrove
Live Music Live Music

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

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Mon, December 23

Alex Napier Duo – Main Stage

Seagrove
Live Music Live Music

The Alex Napier Duo will be performing live from 6 to 9 PM.

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Tue, December 24

Christmas Eve

Seagrove
Markets & Shopping Markets & Shopping

On Christmas Eve, the establishment will be open from 11 AM to 7 PM, providing an ideal opportunity for individuals to complete their tasks before enjoying the evening festivities.

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Tue, December 24

Christmas Eve Dinner featuring Live Violin Holiday Music

Seagrove
Food & Drink Food & Drink

The magic of the season is celebrated with a Christmas Eve Dinner at Old Florida Fish House, available from 4:30 PM to 8 PM. Guests can enjoy the enchanting sounds of live holiday music performed on the violin. The festive menu and cozy ambiance provide the perfect setting for creating cherished holiday memories with family and friends.

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Thu, December 26

Russ Whitten – Lakeside

Seagrove
Live Music Live Music

Russ Whitten can be seen performing live from 4:30 to 8:30 PM.

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Thu, December 26

Dueling Piano – Main Stage

Seagrove
Live Music Live Music

Dueling Piano can be enjoyed live from 7 to 10 PM.

Learn More
Fri, December 27

Russ Whitten – Lakeside

Seagrove
Live Music Live Music

Russ Whitten can be seen performing live from 4:30 to 8:30 PM.

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Fri, December 27

Dueling Piano – Main Stage

Seagrove
Live Music Live Music

Dueling Piano can be enjoyed live from 7 to 10 PM.

Learn More
Sat, December 28

David Martin – Lakeside

Seagrove
Live Music Live Music

David Martin can be seen live from 5 to 9 PM.

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Sat, December 28

Dueling Piano – Main Stage

Seagrove
Live Music Live Music

Dueling Piano can be enjoyed live from 7 to 10 PM.

Learn More
Sun, December 29

Alex Napier – Main Stage

Seagrove
Live Music Live Music

Alex Napier will be performing live on the Main Stage from 7 to 10 PM.

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Mon, December 30

Alex Napier Duo – Main Stage

Seagrove
Live Music Live Music

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

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Tue, December 31

New Year's Eve

Seagrove
Food & Drink Food & Drink

Attendees are invited to experience an unforgettable evening celebrating the New Year at the Old Florida Fish House, renowned as the premier party destination on 30A.

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Tue, December 31

New Year's Eve Dinner 2024

Seagrove
Food & Drink Food & Drink

As the year draws to a close, Surfing Deer is excited to announce its much-anticipated New Year's Eve celebration. This event has become a beloved tradition on the scenic 30A, making Surfing Deer the preferred destination for an unforgettable New Year's Eve experience. The celebration features an exclusive five-course prix fixe dinner menu, which includes vegan options and curated optional wine pairings. This marks the ninth consecutive year that Surfing Deer has hosted this renowned event, cherished by both locals and visitors. The five-course menu offers a variety of exceptional options, including choices for plant-based guests. Chef Greggory Smith has crafted a new menu for the 2024 festivities. A preview of the menu includes House Made Dinner Rolls with Pumpkin Butter for the first course. For the second course, guests can choose between Braised Elk Ravioli or Tempura Battered Cauliflower. The third course offers a choice of French Onion Soup with Beef Short Rib or a Little Gem Salad. For the main course, Chef Gregg will prepare options such as Blackened Red Snapper, Chargrilled Bison Tenderloin, Seared Yellowfin Tuna, or Creamy Pesto Pappardelle. Dessert options include Pear & Frangipane Tartlet, Chocolate Marquise, or Granny Smith Apple & Cranberry Crisp. The cost of this five-course chef-curated experience is $150.00 per person, with an additional wine pairing option available for $65.00 per person. Guests will enjoy the ambiance of Surfing Deer on New Year's Eve. This acclaimed event is highly sought after and has consistently sold out early in previous years, so guests are encouraged to make reservations promptly to secure their spot at the celebration. For reservations or further inquiries, guests can contact Surfing Deer at (850) 213-4200 or visit their reservation page. Don't miss the chance to be part of the unforgettable New Year's Eve celebration at Surfing Deer. For more information about Surfing Deer and Hartley Restaurant Group, please visit their website or follow Surfing Deer on social media.

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Tue, December 31

NYE Celebration with 5-piece band Daybreak featuring local favorite Alex Napier

Seagrove
Live Music Live Music

Old Florida Fish House offers an unforgettable New Year's celebration featuring live music by the energetic five-piece band, Daybreak, which includes the popular local artist, Alex Napier. The festivities begin at 9:30 PM and continue until 12:30 AM, providing a perfect mix of music, fun, and festive atmosphere to welcome 2024.

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Tue, December 31

Alex Napier & Band

Seagrove
Live Music Live Music

Alexi Napier and Band invite everyone to celebrate the New Year with an unforgettable event. The celebration will feature electrifying live music on the Main Stage. The festivities begin at 10:00 PM, promising an evening filled with energy, rhythm, and the magic of the countdown.

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Reviews - 10

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
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!

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

Grayton

Danny West
Joseph Hunter
Jacob Scali
Theresa Byess
Charles McTear
Anna Munzer
Haylee Macon
Chris Parsons
Ryan Pearson
Acquired in 2014 and fully renovated in 2019, the Grayton Office is solely used to provide the fastest hospitality to the homes that are just a stone’s throw away.

Office location:

Grayton, Florida

Contact Grayton
Guests

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