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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Jolly Roger: Amazing Carriage House - South of 30A with Gulf Views!

Bedrooms 2
Space 750 sq ft
Property type cottage
Minimum Stay 1 - 3 nights


About the property

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!


- Master bedroom: king bed with full private bathroom

- Loft: Two twin bed with one trundle bed and full private bathroom


- Wrap around porch with a Gulf view

- 2 complimentary adult bikes

- Private parking

- Outdoor shower

- Wifi

- Pets considered

** Guest responsible for providing beach and pool towels


- 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


• 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.

Call, text or email for more information or to book this beautiful property.

More Details

Property Manager
Gary Pool - Barefoot Vacations
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Manager indicates their response time is:
Within an hour
Calendar last updated:
April 22, 2018


Rosemary Beach Cottage Accommodation and Amenities

Property Type:
  • cottage
Floor Area:
  • 750 sq ft
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 5
  • Max. adults: 5
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets considered
  • Non smoking only
Location Type:
  • Ocean View
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Parking
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Microwave
  • Oven
  • 2 Bathrooms
  • 2 Bedrooms, Sleeps 5
  • 1 King, 3 Twin
  • DVD Player
  • Satellite / Cable
  • Balcony
  • Bicycles
Pool / Spa:
  • Communal Pool
  • restaurants
Leisure Activities:
  • shopping
Local Services & Businesses:
  • fitness center
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • swimming
  • tennis


Excellent! 4.6/5 -
(16 traveler reviews)

75% Complete
18% Complete
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Jolly Roger: Amazing Carriage House - South of 30A with Gulf Views!
average rating of 4.625 based on 16 reviews

Clean, close to the beach. Perfect for a family of 4.

  • 5 of 5

The Jolly Roger was great. The proximity to the beach, restaurants and shopping was very convenient. The house was clean and though small, thoughtfully laid out to maximize space. My family of 4 (2 teenagers) never felt cramped. Would recommend it to anyone.

  • Submitted: Apr 3, 2018
  • Stayed: March 2018
  • Source: VRBO, from HomeAway
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0 0

Great location!

  • 5 of 5

Loved it! Great for a family of 4.

  • Submitted: Apr 2, 2018
  • Stayed: March 2018
  • Source: VRBO, from HomeAway
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0 0

Perfect location & cozy

  • 5 of 5

Love it! Walking distance to beach and restaurants. Kitchen has everything you need, except I would bring counter spray to keep the granite counters clean. Would definitely stay again!

  • Submitted: Feb 19, 2018
  • Stayed: February 2018
  • Source: HomeAway
Owner's Response: Thank you Kathryn for your 5 star review of Jolly Rogers! We appreciate that you chose our home for your vacation and hope that you will return in the future!
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1 0
Raleigh, NC

Perfect for our anniversary getaway!

  • 5 of 5

My wife and I stayed at the Jolly Roger the 2nd week in November for an anniversary trip. It was plenty of space for a couple- and just enough for a family of 4 with 2 twin beds in the loft. We ate every meal out, but if you want to cook in you should be aware this unit doesn't have a dining table. There are 2 barstools at the counter. But with the plentiful food choices in the area, that wasn't a concern for us. The location makes the beach an easy walk. The King bed was comfy and the shower in the master bad had phenomenal water pressure. The property manager was responsive and pleasant when we woke our first morning there to find the power turned off and jackhammers tearing up the street to move a power transformer.

  • Submitted: Nov 16, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
Owner's Response: Very happy you enjoyed your stay. I wish we both had got notification on the move of the transformer! Hope you will choose to stay with us again.
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0 0

Girls trip

  • 4 of 5

Would come back

  • Submitted: Oct 29, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for your review. I'm glad the house worked for your trip.
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2 0

Great location!

  • 5 of 5

Love our stay at the Jolly Roger for our anniversary weekend! Easy walk to the beach and to shops and restaurants. Kitchen had everything we needed. King bed in master was very comfortable (didn’t use beds upstairs). Comfortable, quiet, clean and convenient. Will book again!

  • Submitted: Oct 26, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for choosing to stay with us! We look forward to your return stay.
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2 0


Car: recommended





  • - Contact us through the "Send Email" button for best rate.
    - All rentals require 11% State and County Tax + Cleaning Fee.
    - Credit Cards Accepted for Additional Processing Fee | eChecks also accepted through our website.
    - Must be 25 or older to Rent - No Exceptions.
    - If applicable, Properties with Private Pools can be heated for an additional fee of $50/day.