Rosemary Beach "Jolly Roger" 35 Town Hall Road - Carriage House
Rosemary Beach, FL
Short Term Rental #STR-075590
Bedrooms 2
Beds 4
Sleeps 5
Full Baths 2
Half Baths 0
HOME HIGHLIGHTS:
- Located in the heart of Rosemary Beach, just a few blocks from the beach
- South of 30A
- Courtyard and fountain
- Pet-friendly
- 2 adult bikes
- Grill
- Community pools
- Complete Clean Linen Participant - ALL linens, including comforter covers, are laundered upon every checkout

DETAILS: Discover a delightful coastal escape at Jolly Roger, a charming pet-friendly Carriage House nestled in the heart of Rosemary Beach— only a 4-minute stroll from the sparkling shoreline! This 2-bedroom, 2-bathroom haven provides a spacious getaway for up to 5 guests, offering a seamless blend of relaxation and convenience. Mornings begin in the private courtyard with a cup of coffee, on the loft’s cushioned bench with a good book, or savoring neighborhood views from the wraparound deck. With access to nearby community pools and other amenities, Jolly Roger is the ultimate home base for an unbelievable beach getaway!

At ground level, the private courtyard offers a peaceful retreat, with cozy seating where guests can enjoy their morning coffee or immerse themselves in a good book. This enclosed area, complete with a fountain, offers the perfect spot for playful dogs to roam freely.

Step into an open, airy living area featuring abundant natural light, soothing neutral tones, and touches of coastal blues. The plush sectional sofa is ideal for curling up after a day in the sun, while the well-stocked kitchen with stainless steel appliances and a breakfast bar for 2 ensures all culinary needs are met. The main floor also boasts a serene primary bedroom with a luxurious king bed, TV, and a private bathroom with a shower. Step out onto the wraparound deck to take in the neighborhood views and bask in the gentle coastal breezes.

A spiral staircase leads to the top floor, where a cozy loft provides a welcoming space for children or additional guests. With 2 twin beds, 1 twin trundle, a private bathroom, and a cushioned reading nook, it’s the perfect retreat for rest and relaxation after a day of adventure.

Enjoy the best of Rosemary Beach at Sea Dog! With on-site parking and 2 complimentary adult bikes, exploring Scenic 30A is a breeze. For beach access, head left on Town Hall Road, follow the path by Pescado Seafood Grill to Water Street, turn left, and continue to Western Green. At the end of the green is the boardwalk and beach! Book now!

SLEEPING ARRANGEMENTS (Sleeps 5):
CARRIAGE HOUSE:
- Primary bedroom: king Bed, Private Bathroom with Shower Only
- Loft: Two Twin Beds with One Trundle Bed, Private Bathroom with Shower Only

You also have access to these fantastic Rosemary Beach amenities:
- Coquina Pool: open daily to residents and guests from 9 am to 9 pm.
- Sky Pool: open daily to residents and guests from 6 am to 10 pm (Adult Only Hours, 6 am-9 am & 8 pm-10 pm)
- Cabana Pool: open daily to residents and guests from 9 am to 9 pm.
- Barbados Pool: open daily to residents and guests from 9 am to 9 pm.

*Your rental property may share a courtyard or lot with a main house that is owner-occupied or rented to separate guests from your party.

Parties, weddings, or events held at the property must be pre-approved in writing by 360 Blue. Otherwise, guests will be subject to HOA, community, and other associated fines.

*This home welcomes up to 2 dogs with an additional, non-refundable pet fee of $400.00, plus tax.


Select your travel dates for exact pricing and to book.

Booking a stay within 48 hours of arrival or for longer than 28 days? Want to extend your existing stay an extra day or more?
Please call our Guest Experience team at 877-550-2017 to confirm availability and complete your reservation at this property.

Booking a stay within 48 hours of arrival or for longer than 28 days?
Please call our Guest Experience team at 877-550-2017 to confirm availability and complete your reservation at this property.

  • Air Conditioning
  • Bathtub
  • Bed Linens
  • Carbon Monoxide Detector
  • Coffee Maker
  • Cooking Basics
  • Water Parks
  • Dishes & Silverware
  • Dishwasher
  • Dryer
  • Essentials
  • Fire Extinguisher
  • Living Room
  • Parking
  • Garden or Backyard
  • Towels
  • Hair Dryer
  • Heating
  • Hot Water
  • Kitchen
  • Laptop Friendly
  • Microwave
  • Oven
  • Patio or Balcony
  • Private Entrance
  • Refrigerator
  • Shampoo
  • Smoke Detector
  • Antiquing
  • Bird Watching
  • Boating
  • Horseback Riding
  • Outlet Shopping
  • Paddle Boating
  • Shopping
  • Wildlife Viewing
  • Stove
  • Near Ocean
  • Television
  • Washer
  • Balcony
  • Bicycle
  • Grill
  • Community Pool
  • Wireless Internet
  • Cycling
  • DeepSea Fishing
  • Fishing
  • Fishing - Bay
  • Fishing - Freshwater
  • Fishing - Surf
  • Golf
  • Hiking
  • Jet Skiing
  • Snorkeling
  • Surfing
  • Swimming
  • Tennis
  • Water Tubing
  • Family
  • Wifi
  • Free wifi
  • Dining table
  • Sailing
  • New Property
  • Fishing- Saltwater
  • Starter Bathroom Amenities
  • Starter Kitchen Amentities
  • Dog Friendly
  • Beach
  • Beach Access
  • Water Sports
  • Scuba Diving
  • Kayaking
AVAILABILITY CALENDAR
Available
Unavailable
Check-in Only
Check-out Only

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    3.3 | 3 Guest Reviews
    Brandon
    April, 2026
    The listing was mostly correct, except the listing indicated there was a grill, but according to the welcome email the grill was only for the main house. The listing also failed to mention that the washer and dryer were located in the garage. The photos were accurate, however, they did not really depict how small the main flour of the carriage house was. There was no place to put suitcases in the bedroom, those need to be in the living room. If there are more than two adults staying here it would be extremely tight on space. Overall, great location, but the layout and use of space is not ideal. I would be hesitant to stay in a carriage house again.
    360 Blue Response
    Thank you for sharing your experience at Jolly Roger Carriage House. We appreciate your feedback on the listing and are working with our team to ensure all pertinent information is corrected. We are pleased that you enjoyed the location, and we hope to welcome you back for a smoother stay in the future. Thank you for being our guest.
    Samantha
    April, 2026
    Great location!
    360 Blue Response
    Thank you for rating your experience at Jolly Roger. We are pleased you enjoyed your stay and hope to welcome you back to the beach soon!
    Jacques
    March, 2026
    We needed to call 4 times before the bike issue was resolved. Internet didn’t work well. Windows were cracked/broken. Grill boy available but thought it was when we booked via VRBO. No potholders. Bottom was the trash wasn’t cleaned. Kitchen floor was swept but not clean. Lots of wear and tear in the place.
    360 Blue Response
    Thank you for sharing your experience at the Jolly Roger Carriage House. We truly appreciate your feedback and apologize that your stay did not meet our standards. We are currently reviewing your concerns with our team and hope to provide you with a better 30A getaway in the future.

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