•
19 reviews
Operated by a Wander partner
Trusted operators, vetted by Wander
Surfin’ Cowboy by Oversee 30A | Perfect in Walton County Awards – Three-Time Diamond Winner – Best Rental Mgmt. 2026, 2025, 2024
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.
Highlights:
📍 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:
Overnight:
FIRST FLOOR
Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.
Bedroom 1
1 bed
Bedroom 2
1 bed
Bedroom 3
1 bed
Bedroom 1
1 bed
Bedroom 2
1 bed
Bedroom 3
1 bed
Sarah N.
•
October 2025
Mary-Elizabeth T.
•
April 2025
Heather M.
•
October 2023
Santa Rosa Beach, Florida 32459, United States
Santa Rosa Beach, Florida, United StatesFree cancellation up to 60 days before check-in. 50% refund up to 30 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Nov 12, 2026 | $105 | Available |
| Nov 13, 2026 | $105 | Available |
| Nov 14, 2026 | $105 | Available |
| Nov 15, 2026 | $105 | Available |
| Nov 16, 2026 | $105 | Available |
| Nov 17, 2026 | $105 | Available |
| Nov 18, 2026 | $105 | Available |
| Nov 19, 2026 | $105 | Available |
| Nov 20, 2026 | $105 | Available |
| Nov 21, 2026 | $249 | Available |
| Nov 22, 2026 | $249 | Available |
| Nov 23, 2026 | $249 | Available |
| Nov 24, 2026 | $249 | Available |
| Nov 25, 2026 | $249 | Available |
| Nov 26, 2026 | $249 | Available |
| Nov 27, 2026 | $249 | Available |
| Nov 28, 2026 | $249 | Available |
| Nov 29, 2026 | $105 | Available |
| Nov 30, 2026 | $105 | Available |
| Dec 1, 2026 | $105 | Available |
| Dec 2, 2026 | $105 | Available |
| Dec 3, 2026 | $105 | Available |
| Dec 4, 2026 | $105 | Available |
| Dec 5, 2026 | $105 | Available |
| Dec 6, 2026 | $105 | Available |
| Dec 7, 2026 | $105 | Available |
| Dec 8, 2026 | $105 | Available |
| Dec 9, 2026 | $105 | Available |
| Dec 10, 2026 | $113 | Available |
| Dec 11, 2026 | $115 | Available |
| Dec 12, 2026 | $119 | Available |
| Dec 13, 2026 | $116 | Available |
| Dec 14, 2026 | $113 | Not Available |
| Dec 15, 2026 | $112 | Not Available |
| Dec 16, 2026 | $112 | Not Available |
| Dec 17, 2026 | $105 | Available |
| Dec 18, 2026 | $105 | Available |
| Dec 19, 2026 | $126 | Not Available |
| Dec 20, 2026 | $127 | Not Available |
| Dec 21, 2026 | $137 | Not Available |
| Dec 22, 2026 | $138 | Not Available |
| Dec 23, 2026 | $145 | Not Available |
| Dec 24, 2026 | $149 | Not Available |
| Dec 25, 2026 | $151 | Not Available |
| Dec 26, 2026 | $162 | Not Available |
| Dec 27, 2026 | $195 | Not Available |
| Dec 28, 2026 | $202 | Not Available |
| Dec 29, 2026 | $203 | Not Available |
| Dec 30, 2026 | $219 | Not Available |
| Dec 31, 2026 | $222 | Not Available |
| Jan 1, 2027 | $225 | Not Available |
| Jan 2, 2027 | $165 | Available |
| Jan 3, 2027 | $165 | Available |
| Jan 4, 2027 | $165 | Available |
| Jan 5, 2027 | $165 | Available |
| Jan 6, 2027 | $165 | Available |
| Jan 7, 2027 | $165 | Available |
| Jan 8, 2027 | $165 | Available |
| Jan 9, 2027 | $165 | Available |
| Jan 10, 2027 | $165 | Available |
| Jan 11, 2027 | $165 | Available |
| Jan 12, 2027 | $165 | Available |
| Jan 13, 2027 | $165 | Available |
| Jan 14, 2027 | $165 | Available |
| Jan 15, 2027 | $165 | Available |
| Jan 16, 2027 | $165 | Available |
| Jan 17, 2027 | $165 | Available |
| Jan 18, 2027 | $165 | Available |
| Jan 19, 2027 | $165 | Available |
| Jan 20, 2027 | $165 | Available |
| Jan 21, 2027 | $165 | Available |
| Jan 22, 2027 | $165 | Available |
| Jan 23, 2027 | $165 | Available |
| Jan 24, 2027 | $165 | Available |
| Jan 25, 2027 | $165 | Available |
| Jan 26, 2027 | $165 | Available |
| Jan 27, 2027 | $165 | Available |
| Jan 28, 2027 | $165 | Available |
| Jan 29, 2027 | $165 | Available |
| Jan 30, 2027 | $165 | Available |
| Jan 31, 2027 | $165 | Available |
| Feb 1, 2027 | $165 | Available |
| Feb 2, 2027 | $165 | Available |
| Feb 3, 2027 | $165 | Available |
| Feb 4, 2027 | $165 | Available |
| Feb 5, 2027 | $165 | Available |
| Feb 6, 2027 | $165 | Available |
| Feb 7, 2027 | $165 | Available |
| Feb 8, 2027 | $165 | Available |
| Feb 9, 2027 | $165 | Available |
| Feb 10, 2027 | $165 | Available |