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
  • No petsNo pets

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

Sun, April 27

Olivia Nagy

Seacrest
Live Music Live Music

Olivia Nagy will be performing live from 6:00 to 9:30 PM.

Learn More
Mon, April 28

Tom Paquette

Seacrest
Live Music Live Music

Tom Paquette will be performing live from 6:00 to 9:30 PM.

Learn More
Tue, April 29

Timmy Hood

Seacrest
Live Music Live Music

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

Learn More
Wed, April 30

Joe Forte

Seacrest
Live Music Live Music

Joe Forte will be performing live from 6:00 to 9:30 PM.

Learn More
Thu, May 1

Chris McKay

Seacrest
Live Music Live Music

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

Learn More
Fri, May 2

Tom Pacquette

Seacrest
Live Music Live Music

Tom Pacquette will be performing live from 6:00 to 9:30 PM.

Learn More
Sat, May 3

Timmy Hood

Seacrest
Live Music Live Music

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

Learn More
Sun, May 4

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, May 5

Steven Theriot

Seacrest
Live Music Live Music

Steven Theriot will be performing live from 6:00 to 9:30 PM.

Learn More
Wed, May 7

Christon Birge

Seacrest
Live Music Live Music

Christon Birge will be performing live from 6:00 to 9:30 PM.

Learn More
Sat, May 10

Jared Herzog

Seacrest
Live Music Live Music

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

Learn More
Sun, May 11

String Theory

Seacrest
Live Music Live Music

String Theory will perform live from 6:00 to 9:30 PM.

Learn More
Mon, May 12

Kyle Lamonica

Seacrest
Live Music Live Music

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

Learn More
Tue, May 13

Casey Jordan

Seacrest
Live Music Live Music

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

Learn More

Sun, April 27

Olivia Nagy

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Sunday, April 27, 6:00 pm - 9:30 pm

In 0 days

Olivia Nagy will be performing live from 6:00 to 9:30 PM.

Mon, April 28

Tom Paquette

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Monday, April 28, 6:00 pm - 9:30 pm

In 1 days

Tom Paquette will be performing live from 6:00 to 9:30 PM.

Tue, April 29

Timmy Hood

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Tuesday, April 29, 6:00 pm - 9:30 pm

In 2 days

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

Wed, April 30

Joe Forte

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Wednesday, April 30, 6:00 pm - 9:30 pm

In 3 days

Joe Forte will be performing live from 6:00 to 9:30 PM.

Thu, May 1

Chris McKay

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Thursday, May 1, 6:00 pm - 9:30 pm

In 4 days

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

Fri, May 2

Tom Pacquette

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Friday, May 2, 6:00 pm - 9:30 pm

In 5 days

Tom Pacquette will be performing live from 6:00 to 9:30 PM.

Sat, May 3

Timmy Hood

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Saturday, May 3, 6:00 pm - 9:30 pm

In 6 days

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

Sun, May 4

Sundown Strays (Rob Cathcart)

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Sunday, May 4, 6:00 pm - 9:30 pm

In 7 days

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

Mon, May 5

Steven Theriot

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Monday, May 5, 6:00 pm - 9:30 pm

In 8 days

Steven Theriot will be performing live from 6:00 to 9:30 PM.

Wed, May 7

Christon Birge

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Wednesday, May 7, 6:00 pm - 9:30 pm

In 10 days

Christon Birge will be performing live from 6:00 to 9:30 PM.

Sat, May 10

Jared Herzog

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Saturday, May 10, 6:00 pm - 9:30 pm

In 13 days

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

Sun, May 11

String Theory

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Sunday, May 11, 6:00 pm - 9:00 pm

In 14 days

String Theory will perform live from 6:00 to 9:30 PM.

Mon, May 12

Kyle Lamonica

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Monday, May 12, 9:00 am - 3:00 pm

In 15 days

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

Tue, May 13

Casey Jordan

Seacrest
Live Music Live Music
Where:

Peddlers' Pavilion

10343 E. County Hwy 30A, seacrest, 32413

When:

Tuesday, May 13, 7:00 pm - 9:00 pm

In 16 days

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

Host Family

Emerald Office at Sunnyside

Daniel Cecil
Skyler Lanave
Jing Moore
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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