Jolly Roger


2 Bedrooms / 2 Bathrooms / Sleeps 5
Cottage in Rosemary Beach

Property Details

***Please note: Rosemary Beach community pools are open. Occupancy is limited to 50%; first come first serve. Rosemary Beach has the right of refusal and the right to close the pools at any time if current CDC Guidelines regarding social distancing are not being met.***

Jolly Roger is a beautiful 2 bedroom, 2 bathroom carriage home perfectly located within Rosemary Beach. This home features a private parking area and entrance through the courtyard, with a lovely view of the Gulf from its balcony. Once inside you will find a bright and open living area cozy enough for every guest to unwind. The adjoining kitchen is fully stocked with all the tools you need for meal prep. It features stainless steel appliances and a bar with seating for two guests. Just around the corner is the master bedroom featuring a king bed and a full private bathroom with a glass-enclosed shower. The loft area can be found just up the spiral staircase. The loft features two twin beds and one trundle bed, accommodating 3 guests. There is a full private bathroom on this level as well as a built-in sitting area with wonderful views of the town of Rosemary.

Located just 2.5 blocks from the shores of the Gulf, 1 block away from the Barbados Pool, and a short walk to the Rosemary Town Center, you are sure to have a fabulous time during your stay at Jolly Roger!

Book this vacation home now, or Contact us for more information or to book this beautiful property.

Sleeping Arrangements


  • Master bedroom: king bed with full private bathroom
  • Loft: Two twin bed with one trundle bed and full private bathroom

Home Highlights

  • Wrap around porch
  • Private parking
  • Outdoor shower
  • Wifi
  • Pets considered (Must receive approval, please include breed and age of dog in your inquiry e-mail notes)
    *** Guest responsible for providing beach and pool towels ***

Rosemary Amenities

  • Private beach access
  • Access to 4 community pools
  • Beach chair and umbrella rental service available
  • Fitness center (additional fees apply)
  • Access to tennis courts
  • Walking trails
  • 24 hour security

Booking Calendar

Booking Policy

    • A 50% Advance Deposit is due at the time of booking.
    • Balance is due 30 days prior to arrival date.
    • With the exception of a cancellation fee, deposits are fully refundable if cancellations are given 90 days prior to arrival date.
    • We accept e-checks or credit cards (Additional fee applies for all credit card transactions).
    • Check-In begins at 4:00PM CST. If available, an early check-in may be requested for an additional fee.
    • Check-Out is by 10:00AM CST. If available, a late check-out may be requested for an additional fee.
    • Must Be 25 Or Older To Rent. We have a strict family only policy. No exceptions.


Air Conditioning
Central Heat
Clothes Dryer
Hair Dryer
Internet – Hi Speed
Internet – Wireless
Iron and Board
Linens Provided
Towels Provided
Washing Machine

Near Ocean


Fitness Center

Wraparound Porch

Coffee Maker

Satellite / Cable

Communal Pool




Great Weekend Getaway

Great weekend getaway for my wife and I. Perfect spot to Rosemary square and short walk to Seacrest & Alys Beach. Carriage house is perfect size. Parking spot in garage is a bit tight with a larger SUV so we parked on street. February not an issue, but summertime could be tough parking with larger vehicle. Overall exactly what we were looking for for a spot in Rosemary!

Jonathan L.

5/5 Stayed Feb 2020

Amazing little place in Rosemary Beach!

Just returned from a long weekend with the family at the Jolly Roger in Rosemary Beach. It could not have gone better. Great location, excellent condition, easy Check-in. Loved it! Already booked it again in the future. Kids can’t wait!

Chad M.

5/5 Stayed Aug 2019

Great experience

We had a wonderful stay and hope to stay again soon!

Barrett O.

5/5 Stayed Aug 2019

Excellent Experience…

Great location, close to the pool, beach and all the Shops…Also Amazing Church service at the town hall.

Jay E. Nashville, TN

5/5 Stayed Jun 2019

Pet Policy

    The home is pet friendly for APPROVED pets only for a (non-refundable) Additional Fee:
  • Small or Medium sized dogs ONLY
  • Non-Shedding
  • House-Trained
  • Maximum of 2 Dogs



Phone: (850) 278-6357

Mailing Address:
4942 US Highway 98 W - Suite 24
Santa Rosa Beach, FL 32459

Or use the contact form below to send us a message.