Pirate's Smile
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Pirate's Smile
Pirate's Smile by Oversee 30A | 2025 Diamond Winner-Best Rental Mgmt.
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.
Highlights:
📍 Seacrest Beach
👣 630 steps (.3 mile) to private beach access
🛏️ 4 bedrooms, 3.5 baths
👙 Giant community pool!
😎 Community tram
🚿 Outdoor shower
🚲 4 bikes
🕶️ Explore Seacrest, Rosemary Beach, and Alys Beach
🦞 4-star restaurants
🛍️ Fun eateries and boutiques
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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Pet friendly
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
Entertainment
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Cable
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Smart TV
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
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
Primary Bed Bedroom
1 King bed
full bathroom
full bathroom
half bathroom
Location
Upcoming Events
Live Music with Tanner Lee Gray
Seacrest
Live Music
Tanner Lee Gray will be performing live from 6 to 9 PM.
Timmy Hood
Seacrest
Live Music
Timmy Hood will be performing live from 6:00 to 9:30 PM.
Chris McKay
Seacrest
Live Music
Chris McKay will be performing live from 6:00 to 9:30 PM.
Kristi Allen
Seacrest
Live Music
Kristi Allen will be performing live from 6:00 to 9:30 PM.
David Auen
Seacrest
Live Music
David Auen will be performing live from 6:00 to 9:30 PM.
Jared Herzog
Seacrest
Live Music
Jared Herzog will perform live from 6:00 to 9:30 PM.
Tue, May 20
Live Music with Tanner Lee Gray
Seacrest
Live Music
Tanner Lee Gray will be performing live from 6 to 9 PM.
Tue, May 20
Timmy Hood
Seacrest
Live Music
Timmy Hood will be performing live from 6:00 to 9:30 PM.
Wed, May 21
Chris McKay
Seacrest
Live Music
Chris McKay will be performing live from 6:00 to 9:30 PM.
Thu, May 22
Kristi Allen
Seacrest
Live Music
Kristi Allen will be performing live from 6:00 to 9:30 PM.
Fri, May 23
David Auen
Seacrest
Live Music
David Auen will be performing live from 6:00 to 9:30 PM.
Sat, May 24
Jared Herzog
Seacrest
Live Music
Jared Herzog will perform live from 6:00 to 9:30 PM.
Reviews - 4
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