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
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Bathtub
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
Kyle Lamonica
Seacrest
Live Music
Kyle Lamonica will perform live 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 a weekly Music Bingo event every Wednesday at 6 PM. This free-to-play activity offers participants the chance to win prizes while enjoying a selection of thirty craft beers, wine, and frozen cocktails. Although the venue focuses on providing cold beverages, guests are welcome to bring their own food or order delivery to the site.
Pickl’d Coast Shoppy Hour – Pickle, Shop, & Sip
Seacrest
Live Music
Nicole Rayne performs 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 p.m. The venue features thirty craft beers on tap, frozen rosé, piña coladas, and a selection of wines. While the establishment focuses on providing cold drinks and a relaxed atmosphere, guests are welcome to bring their own food or order delivery during their visit.
Nate Kelly
Seacrest
Live Music
Nate Kelly performs 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 starting at 6 PM. The venue features a selection of thirty beers on tap, wine by the glass, and frozen cocktails such as rosé and piña coladas. Focusing on cold drinks and a relaxed atmosphere, the establishment encourages guests to bring their own food or order delivery to enjoy while they visit.
String Theory
Seacrest
Live Music
String Theory performs live from 6:00 PM to 9:30 PM.
Jared Herzog
Seacrest
Live Music
Jared Herzog performs live from 6:00 PM to 9:30 PM.
Weston Hine
Seacrest
Live Music
Weston Hine performs live from 6:00 to 9:30 PM.
Kyle Lamonica
Seacrest
Live Music
Kyle Lamonica will perform live from 6:00 to 9:30 PM.
Chris McKay
Seacrest
Live Music
Chris McKay will be performing a live set from 6:00 PM until 9:30 PM.
Brett Stafford Smith
Seacrest
Live Music
Brett Stafford Smith will perform a live musical set from 6:00 PM to 9:30 PM.
Music Bingo
Seacrest
Food & Drink
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 beers on tap, frozen cocktails, and wine. 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 and Brew on 30A hosts live music every Thursday starting at 6:00 PM. The venue offers 30 draft beers, wine by the glass, and frozen drinks such as rosé and piña coladas. While the establishment focuses on providing cold beverages and a relaxed atmosphere, guests are welcome to bring their own food or have it delivered while they enjoy their visit.
Otha Allen
Seacrest
Live Music
Attendees can experience a live performance by Otha Allen between 6:00 PM and 9:30 PM.
David Auen
Seacrest
Live Music
David Auen will be performing 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 a selection of 30 draft beers, wine by the glass, and frozen drinks like rosé and piña coladas. While the establishment focuses on providing a relaxing atmosphere with cold beverages, guests are welcome to bring their own food or order delivery to the location.
Jared Herzog
Seacrest
Live Music
Jared Herzog will be performing live from 6:00 PM to 9:30 PM.
Mon, May 18
Kyle Lamonica
Seacrest
Live Music
Tue, May 19
Gage Cowart
Seacrest
Live Music
Wed, May 20
Music Bingo
Seacrest
Sports & Games
Wed, May 20
Pickl’d Coast Shoppy Hour – Pickle, Shop, & Sip
Seacrest
Live Music
Thu, May 21
Live Music
Seacrest
Live Music
Thu, May 21
Nate Kelly
Seacrest
Live Music
Fri, May 22
Live Music
Seacrest
Live Music
Fri, May 22
String Theory
Seacrest
Live Music
Sat, May 23
Jared Herzog
Seacrest
Live Music
Sun, May 24
Weston Hine
Seacrest
Live Music
Mon, May 25
Kyle Lamonica
Seacrest
Live Music
Tue, May 26
Chris McKay
Seacrest
Live Music
Wed, May 27
Brett Stafford Smith
Seacrest
Live Music
Wed, May 27
Music Bingo
Seacrest
Food & Drink
Thu, May 28
Live Music
Seacrest
Live Music
Thu, May 28
Otha Allen
Seacrest
Live Music
Fri, May 29
David Auen
Seacrest
Live Music
Fri, May 29
Live Music
Seacrest
Live Music
Sat, May 30
Jared Herzog
Seacrest
Live Music
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