Pirate's Smile
Pirate's Smile
Pirate's Smile
Pirate's Smile
Pirate's Smile by Oversee 30A | Perfect in Walton County Awards – Three-Time Diamond Winner – Best Rental Mgmt. 2026, 2025, 2024
Pirate's Smile is all about relaxed luxury, blending comfort and plenty of entertainment. Each bedroom features ultra-modern 4K Smart TVs and premium mattresses, while a private outdoor shower and five unique porches add to the charm.
Resting on a spacious corner lot on the west side of the neighborhood, this home has plenty of parking and easy access to the community pool, with Rosemary Beach and Alys Beach just a short stroll away.
Inside, the living room is designed for unwinding, with a 75” 4K Ultra HD TV, DVR, and premium movie channels. The ultra-comfy sectional might make you want to skip the beach altogether! High-speed internet and a handy workspace in the living room ensure you can stay connected when needed.
Step outside to a back deck made for lounging. The summer kitchen, gas grill, cozy seating, and a 58” 4K TV make this the perfect spot to gather, grill, and relax.
The open gourmet kitchen is a dream for cooking and entertaining.
With seating for eight at the dining table and three at the island, it’s great for group meals. Turkish marble countertops, high-end appliances, and a fully stocked kitchen make cooking a pleasure.
On the first floor, the Scallywag Suite offers a peaceful retreat with a king-sized bed, memory foam mattress, and en suite bathroom with a walk-in shower. A 58” 4K TV completes the space.
Upstairs, three more bedrooms await. The second-floor Captain’s Quarters is the primary suite you won’t want to leave. A king bed with a pillow-top mattress, a luxurious bathroom with a soaking tub, and a private veranda with comfy seating make this space a dream. You’ll also find a 65” curved 4K TV with premium channels for added indulgence.
Blackbeard’s Escape is another primary bedroom, king, with a vanity area and a shared Jack-and-Jill bathroom leading to Buccaneers’ Bunks, featuring custom-built bunk beds, storage, and charging stations. The kids have their own 58” 4K TV and Blu-Ray/DVD player for movie nights. The Crow’s Nest, with a queen sleeper sofa, is perfect for extra guests.
The beach is just across the street, and the community tram can take you there or to the 12,000-square-foot lagoon pool. In the summer, poolside snacks and a seasonal grill add to the fun!
Overview:
- 630 steps (.3 mile) to private beach access
- Giant community pool, 12,000 sq ft!
- 4 bedrooms, 3.5 baths
- Community tram
- Porch with gas grill, seating, TV
- Outdoor shower
- Wi-Fi
Overnight:
1ST FLOOR
- Primary Bedroom, King Bed, En Suite Bathroom, Walk-in Shower, TV
2ND FLOOR
- Primary Bedroom, King Bed, Double Vanity, Walk-in Shower, Tub, Private Veranda
- Primary Bedroom, King Bed, Vanity Area, Walk-in Shower, Share a Shower/Tub
- Bunk Room, 2 Custom Twin/Twin Bunks, Private Half Bath, Share a Shower/tub
- Landing Area, Sleeper Sofa, Queen
Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.
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Hassle-free check-in.
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Add your trip dates to get the cancellation details for this stay.
House Rules
Who can stay.
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12 guests maximum
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No pets
What's allowed.
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Check-in after 4:00 PM
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Check-out before 10:00 AM
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No smoking
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No parties or events
Amenities
Community Amenities
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Community pool
Outdoor
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Balcony
Indoor
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Wireless internet
Safety Features
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Carbon monoxide detector
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Fire extinguisher
Kitchen
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Standard coffee maker
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Microwave
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Refrigerator
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Toaster
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Dishwasher
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Stove
Bed And Bathroom
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Hair dryer
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Iron & board
Entertainment
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Smart TV
Complimentary Items
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4 Oversee bikes
Bed and Baths
1st Floor
bedroom
1 King bed
full bathroom
2nd Floor
bedroom
1 King bed
bedroom
2 Bunk beds
common
1 Sofa bed
Primary Bed Bedroom
1 King bed
full bathroom
full bathroom
half bathroom
Location
Upcoming Events
Steven Theriot
Seacrest
Live Music
Steven Theriot will perform a live set from 6:00 PM to 9:30 PM.
Kyle Lamonica
Seacrest
Live Music
Kyle Lamonica will perform a live musical set from 6:00 PM to 9:30 PM.
Chris McKay
Seacrest
Live Music
Chris McKay will perform a live set from 6:00 PM to 9:30 PM.
Music Bingo
Seacrest
Sports & Games
Beach & Brew on 30A hosts Music Bingo every Wednesday at 6 PM. This free event offers participants a fun night of music, drinks, and prizes in a relaxed atmosphere. The venue features thirty beers on tap along with wine and frozen cocktails like rosé and piña coladas. Guests are encouraged to arrive early to secure a table and are welcome to bring their own food or order delivery to enjoy while they play.
Nate Kelly
Seacrest
Live Music
Nate Kelly will perform a live set from 6:00 PM to 9:30 PM.
Christon Birge
Seacrest
Live Music
Christon Birge will perform a live musical set from 6:00 PM to 9:30 PM.
Live Music
Seacrest
Live Music
Beach & Brew on 30A hosts live music every Thursday at 6:00 PM. The venue offers a selection of 30 beers on tap, frozen cocktails like rosé and piña coladas, and wine by the glass. While the establishment focuses on providing drinks and a relaxed atmosphere, guests are welcome to bring their own food or order delivery to enjoy during their visit.
David Auen
Seacrest
Live Music
David Auen will perform a live musical set from 6:00 PM to 9:30 PM.
Live Music
Seacrest
Live Music
Beach & Brew on 30A hosts live music every Friday at 6:00 PM. The venue offers 30 beers on tap, wine by the glass, and frozen drinks like rosé and piña coladas. Guests are encouraged to enjoy the relaxed atmosphere and are welcome to bring their own food or order delivery to the establishment.
Jared Herzog
Seacrest
Live Music
Jared Herzog will perform a live musical set from 6:00 PM to 9:30 PM.
Steven Theriot
Seacrest
Live Music
Steven Theriot will perform a live musical set from 6:00 PM to 9:30 PM.
Kyle Lamonica
Seacrest
Live Music
Kyle Lamonica performs live from 6:00 to 9:30 PM.
Chris McKay
Seacrest
Live Music
Chris McKay performs a live set from 6:00 PM to 9:30 PM.
Gage Cowart
Seacrest
Live Music
Gage Cowart will perform a live musical set from 6:00 PM to 9:30 PM.
Music Bingo
Seacrest
Sports & Games
Beach & Brew on 30A hosts Music Bingo every Wednesday at 6 PM. This free event offers a lively atmosphere with music, prizes, and a selection of thirty craft beers, wine, frozen rosé, and piña coladas. While the venue focuses on providing cold drinks and a relaxed environment, guests are welcome to bring their own food or order delivery to enjoy during the games.
Live Music
Seacrest
Live Music
Beach and Brew on 30A hosts live music every Thursday at 6:00 PM. The venue offers thirty beers on tap, frozen rosé, piña coladas, and various wines by the glass. While the establishment focuses on providing cold drinks and a relaxed atmosphere, guests are encouraged to bring their own food or order delivery while they enjoy the environment.
Otha Allen
Seacrest
Live Music
Otha Allen will perform live from 6:00 PM to 9:30 PM.
Live Music
Seacrest
Live Music
Beach & Brew on 30A hosts live music every Friday starting at 6:00 PM. The venue offers thirty beers on tap, frozen cocktails like rosé and piña coladas, and wine by the glass. While the establishment focuses on providing cold drinks and a relaxed atmosphere, guests are welcome to bring their own food or order delivery to enjoy on-site.
Weston Hine
Seacrest
Live Music
Weston Hine will perform a live musical set from 6:00 PM to 9:30 PM.
Walton County Fore Her Peer Support Group
Seacrest
Workshops & Classes
A peer support group for breast cancer patients and survivors meets on the first Saturday of each month. The sessions are held at the Hive in Panama City from 10:00 AM to 12:00 PM.
Nate Kelly
Seacrest
Live Music
Nate Kelly will perform live from 6:00 PM to 9:30 PM.
Gage Smith
Seacrest
Live Music
Gage Smith will perform a live musical set from 6:00 PM to 9:30 PM.
Kyle Lamonica
Seacrest
Live Music
Kyle Lamonica will perform a live musical set from 6:00 PM to 9:30 PM.
Chris McKay
Seacrest
Live Music
Chris McKay will perform a live set from 6:00 PM to 9:30 PM.
Gage Cowart
Seacrest
Live Music
Gage Cowart will perform a live musical set from 6:00 PM to 9:30 PM.
Music Bingo
Seacrest
Sports & Games
Beach & Brew on 30A hosts Music Bingo every Wednesday at 6 PM, offering a fun evening of music, drinks, and prizes. The event is free to play and features a selection of 30 draft beers, wine, and frozen cocktails like rosé and piña coladas. While the venue focuses on providing cold drinks and a relaxed atmosphere, guests are welcome to bring their own food or order delivery to enjoy during the games.
Live Music
Seacrest
Live Music
Beach & Brew on 30A hosts live music every Thursday at 6:00 PM. The venue features 30 cold beers on tap along with wine by the glass and frozen beverages like rosé and piña coladas. While the establishment focuses on providing drinks and a relaxed atmosphere, guests are welcome to bring their own food or order delivery while they enjoy the experience.
Official After Party
Seacrest
Live Music
Ronni Kay will perform a live show from 6:00 PM to 9:30 PM.
David Auen
Seacrest
Live Music
David Auen will perform a live set from 6:00 PM to 9:30 PM.
Live Music
Seacrest
Live Music
Beach & Brew on 30A hosts live music every Friday at 6 PM. The venue offers thirty cold beers on tap, frozen rosé, piña coladas, and wine by the glass. With a focus on cold drinks and a relaxed atmosphere, guests are welcome to bring their own food or order delivery while they enjoy the music.
Jared Herzog
Seacrest
Live Music
Jared Herzog will perform live from 6:00 PM to 9:30 PM.
Steven Theriot
Seacrest
Live Music
Steven Theriot will perform live from 6:00 PM to 9:30 PM.
Christon Birge
Seacrest
Live Music
Christon Birge will perform live from 6:00 PM to 9:30 PM.
Chris McKay
Seacrest
Live Music
Chris McKay performs live from 6:00 PM to 9:30 PM.
Music Bingo
Seacrest
Sports & Games
Beach and Brew on 30A hosts a weekly Music Bingo event every Wednesday starting at 6 PM. This free-to-play evening features music, prizes, and a variety of beverages, including thirty beers on tap, wine, and frozen cocktails. While the venue focuses on providing drinks and a relaxed atmosphere, guests are encouraged to bring their own food or order delivery to enjoy during the event.
Sun, April 19
Steven Theriot
Seacrest
Live Music
Mon, April 20
Kyle Lamonica
Seacrest
Live Music
Tue, April 21
Chris McKay
Seacrest
Live Music
Wed, April 22
Music Bingo
Seacrest
Sports & Games
Wed, April 22
Nate Kelly
Seacrest
Live Music
Thu, April 23
Christon Birge
Seacrest
Live Music
Thu, April 23
Live Music
Seacrest
Live Music
Fri, April 24
David Auen
Seacrest
Live Music
Fri, April 24
Live Music
Seacrest
Live Music
Sat, April 25
Jared Herzog
Seacrest
Live Music
Sun, April 26
Steven Theriot
Seacrest
Live Music
Mon, April 27
Kyle Lamonica
Seacrest
Live Music
Tue, April 28
Chris McKay
Seacrest
Live Music
Wed, April 29
Gage Cowart
Seacrest
Live Music
Wed, April 29
Music Bingo
Seacrest
Sports & Games
Thu, April 30
Live Music
Seacrest
Live Music
Thu, April 30
Otha Allen
Seacrest
Live Music
Fri, May 1
Live Music
Seacrest
Live Music
Fri, May 1
Weston Hine
Seacrest
Live Music
Sat, May 2
Walton County Fore Her Peer Support Group
Seacrest
Workshops & Classes
Sat, May 2
Nate Kelly
Seacrest
Live Music
Sun, May 3
Gage Smith
Seacrest
Live Music
Mon, May 4
Kyle Lamonica
Seacrest
Live Music
Tue, May 5
Chris McKay
Seacrest
Live Music
Wed, May 6
Gage Cowart
Seacrest
Live Music
Wed, May 6
Music Bingo
Seacrest
Sports & Games
Thu, May 7
Live Music
Seacrest
Live Music
Thu, May 7
Official After Party
Seacrest
Live Music
Fri, May 8
David Auen
Seacrest
Live Music
Fri, May 8
Live Music
Seacrest
Live Music
Sat, May 9
Jared Herzog
Seacrest
Live Music
Sun, May 10
Steven Theriot
Seacrest
Live Music
Mon, May 11
Christon Birge
Seacrest
Live Music
Tue, May 12
Chris McKay
Seacrest
Live Music
Wed, May 13
Music Bingo
Seacrest
Sports & Games
Reviews - 17
Google
We stayed at Pirates Smile in Seacrest Beach for Easter. There were 3 families with children from 18 months to 13 yrs old. The location was perfect with a tram stop at our back door and the perfect neighborhood to bike around. The house was really clean and the beach towels and tumblers were a great surprise! 5/5 would stay here again next year.
Google
Booking with Oversee is a great experience! They are always very helpful and responsive not only during the booking but also during our stays. We rent properties from them every time we come to 30A and couldn’t be happier.
Airbnb
Google
Pirate’s SMile, Seacrest Beach. BEST experience ever. Beautiful, comfortable, amazing location, pool, beach, the thing of dreams!
Airbnb
Great spot with amazing community pool and easy access to the beach!
Airbnb
Airbnb
Beautiful and clean home for a perfect beach getaway in magical town!
Airbnb
The home is large and beautiful. The mangagement staff was helpful and very responsive. Great location to Tram. The bikes were great to have!
Airbnb
Awesome location
Airbnb
Beautiful home in a beautiful community with easy tram access to both seacrest pool and beach. Very family friendly with our two small kids. We highly recommend this home to enjoy all 30A has to offer. Highly recommend! 5 ‚≠êÔ∏è‚’s
Vrbo
Great house in perfect location. Quick walk to the beach and the pool. Owners were very responsive. Very clean.
Airbnb
Great stay, nice house with tram stop directly out the back door. Second floor balcony was very nice and spacious.
Airbnb
Great location to everything. Great space. Clean and tidy. Nice to have washer and dryer to clean your clothes while traveling. The tram is great to get to the beach.
Airbnb
Airbnb
Absolutely amazing
Oversee
Oversee
Having vacationed at Pirate’s Smile multiple times, I can confidently say it’s the epitome of upscale family retreats. Nestled in the serene Seacrest Beach community, this expansive and impeccably maintained home exudes an elevated beach-casual charm that immediately sets the tone for relaxation. The house comfortably accommodates large families, offering ample space and thoughtful amenities. Its proximity to a resort-style lagoon pool and the pristine white sandy beaches ensures that both relaxation and adventure are always within reach. A short stroll or bike ride leads to charming shops, diverse restaurants, and vibrant seasonal events. Exploring the nearby Alys Beach development and attending the local farmers market have become cherished traditions during our stays. For families seeking a luxurious, well-appointed beach getaway that caters to every need and desire, Pirate’s Smile is an unparalleled choice.
Host Family
Emerald Office at Sunnyside
Office location:
Emerald Office at Sunnyside, Florida
Contact Emerald Office at Sunnyside
Pirate's Smile
Seacrest Beach - Sleeps 12
4 bedrooms - 5 beds - 3.5 baths
Prices include all fees and taxes