Pirate's Smile

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

Pirate's Smile by Oversee 30A | 2024 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
👣 Just steps to beach
🛏️ 4 bedrooms, 3.5 baths
👙 Giant community pool!
😎 Community tram
🚿 Outdoor shower
🕶️ 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:
- Just steps to beach
- 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

30A Farmer’s Markets

30A Florida

Harvest Wine & Food Festival: Grand Tasting

Seascape Golf Course

2024 Mountainfilm on Tour

WaterColor

Seeing Red Wine Festival

Seaside Scenic Highway 30-A
seabreeze jazz festival

Seabreeze Jazz Festival

Panama City Beach

30a10k Thanksgiving Day races

Rosemary Beach
30a wine festival

30A Wine Festival

Oversee 30A Beach Vacation Giveaway +1 more

South Walton Beaches Wine & Food Festival: Craft Beer & Spirits Jam

Grand Boulevard Town Center

30a10k Thanksgiving Day races

Rosemary Beach

South Walton Beaches Wine & Food Festival: Craft Beer & Spirits Jam

Grand Boulevard Town Center

30a10k Thanksgiving Day races

Rosemary Beach

South Walton Beaches Wine & Food Festival: Craft Beer & Spirits Jam

Grand Boulevard Town Center

30a10k Thanksgiving Day races

Rosemary Beach

Host Family

Sunnyside

Roy Foreman
Daniel Cecil
Skyler Lanave
Jing Moore
Crystal Becktel
Our Sunnyside Office, acquired in 2017 and fully renovated in 2021, is just down the street from many of our beautiful homes. Its proximity lets us ensure every guest request is met in a timely manner.

Office location:

Sunnyside, Florida

Contact Sunnyside

Pirate's Smile

Rosemary Beach - Sleeps 12

4 bedrooms - 5 beds - 3.5 baths

Guests
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Adults (18+)

Children (2-17)

Infants (0-1)

Pets

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