Pirate's Smile

Sleeps 12 - 4 Bedrooms - 3.5 Baths
109 Woody Wagon Way, Seacrest Beach, Florida 32461

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.
  • Add your trip dates to get the cancellation details for this stay.

House Rules

Who can stay.

  • Guests Maximum12 guests maximum
  • Pet friendlyPet friendly

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 poolCommunity pool

Outdoor

  • BalconyBalcony

Indoor

  • Wireless internetWireless internet

Entertainment

  • CableCable
  • Smart TVSmart TV

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

Complimentary Items

  • 4 Oversee bikes4 Oversee bikes
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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

Fri, June 6

David Auen

Seacrest
Live Music Live Music

David Auen will be performing live from 6:00 to 9:30 PM.

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Sat, June 7

Jared Herzog

Seacrest
Live Music Live Music

Jared Herzog will perform live from 6:00 to 9:30 PM.

Learn More
Sun, June 8

Sundown Strays (Rob Cathcart)

Seacrest
Live Music Live Music

Sundown Strays, featuring Rob Cathcart, will perform live from 6:00 to 9:30 PM.

Learn More
Mon, June 9

Timmy Hood

Seacrest
Live Music Live Music

Timmy Hood will be performing live from 6:00 to 9:30 PM.

Learn More
Tue, June 10

Casey Jordan

Seacrest
Live Music Live Music

Casey Jordan will be performing live from 6:00 to 9:30 PM.

Learn More
Wed, June 11

Chris McKay

Seacrest
Live Music Live Music

Chris Mckay will be performing live from 6:00 to 9:30 PM.

Learn More
Thu, June 12

Nicole Rayne

Seacrest
Live Music Live Music

Nicole Rayne will be performing live from 6:00 to 9:30 PM.

Learn More
Fri, June 13

David Auen

Seacrest
Live Music Live Music

David Auen will be performing live from 6:00 to 9:30 PM.

Learn More
Sat, June 14

Jared Herzog

Seacrest
Live Music Live Music

Jared Herzog will perform live from 6:00 to 9:30 PM.

Learn More
Sun, June 15

Mitchell Edwards

Seacrest
Live Music Live Music

Mitchell Edwards will be performing live from 6:00 to 9:30 PM.

Learn More
Mon, June 16

Kyle Lamonica

Seacrest
Live Music Live Music

Kyle Lamonica will be performing live from 6:00 to 9:30 PM.

Learn More

Fri, June 6

David Auen

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Friday, June 6, 6:00 pm - 9:30 pm

In 0 days

David Auen will be performing live from 6:00 to 9:30 PM.

Sat, June 7

Jared Herzog

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Saturday, June 7, 6:00 pm - 9:30 pm

In 1 days

Jared Herzog will perform live from 6:00 to 9:30 PM.

Sun, June 8

Sundown Strays (Rob Cathcart)

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Sunday, June 8, 6:00 pm - 9:30 pm

In 2 days

Sundown Strays, featuring Rob Cathcart, will perform live from 6:00 to 9:30 PM.

Mon, June 9

Timmy Hood

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Monday, June 9, 6:00 pm - 9:30 pm

In 3 days

Timmy Hood will be performing live from 6:00 to 9:30 PM.

Tue, June 10

Casey Jordan

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Tuesday, June 10, 6:00 pm - 9:30 pm

In 4 days

Casey Jordan will be performing live from 6:00 to 9:30 PM.

Wed, June 11

Chris McKay

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Wednesday, June 11, 6:00 pm - 9:30 pm

In 5 days

Chris Mckay will be performing live from 6:00 to 9:30 PM.

Thu, June 12

Nicole Rayne

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Thursday, June 12, 6:00 pm - 9:30 pm

In 6 days

Nicole Rayne will be performing live from 6:00 to 9:30 PM.

Fri, June 13

David Auen

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Friday, June 13, 6:00 pm - 9:30 pm

In 7 days

David Auen will be performing live from 6:00 to 9:30 PM.

Sat, June 14

Jared Herzog

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Saturday, June 14, 6:00 pm - 9:30 pm

In 8 days

Jared Herzog will perform live from 6:00 to 9:30 PM.

Sun, June 15

Mitchell Edwards

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Sunday, June 15, 6:00 pm - 9:30 pm

In 9 days

Mitchell Edwards will be performing live from 6:00 to 9:30 PM.

Mon, June 16

Kyle Lamonica

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Monday, June 16, 6:00 pm - 9:30 pm

In 10 days

Kyle Lamonica will be performing live from 6:00 to 9:30 PM.

Reviews - 4

james
, KY
Feb 2025 Airbnb
christopher
Jan 2025 Airbnb

Absolutely amazing

shari
, SC
Oversee
This beach house is located  close to everything. Park your car and  walk or bike to shops, restaurants, the beach or the fantastic pool.  The house is perfect for large families, with open spaces for reading or just lounging.  The kitchen is well equipped for cooking local seafood. On Sunday mornings a wonderful farmers market is close by for shopping for fresh seafood, local honey, baked breads, fresh produce, pickles and homemade spice blends, just to name a few.  My family had everything we needed and more for a great week on 30-A at the home. We will be back.
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robert
Atlanta, GA
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.

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Host Family

Emerald Office at Sunnyside

Jing Moore
Daniel Cecil
Skyler Lanave
Ranzi Veale
The Emerald Office takes care of our homes to the east of Camp Creek Lake, making it simple for our team to be close when you need us, ensuring every detail of your stay is covered.

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

Guests
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Adults (18+)

Children (2-17)

Infants (0-1)

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