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Vacation Rental Management & Design



About us

Jon & Courtney Schomburg

Hi! We are Jon and Courtney Schomburg. We recently moved here to sunny Sarasota to pursue our dreams of owning and renting out beautiful beach homes. I am an Interior Decorator, Home Stager and Realtor. I love decorating houses in a fun beachy vibe. Jon is a talented musician and an amazing Dad to our seven year old daughter. He is always there to crack a joke or help out whenever possible. I will be the one you are communicating with throughout your stay and my mission is to make your vacation the most memorable one ever! Together we make the perfect team. Yin and Yang. Perfectionist and laid back. Creative and analytical. We have it all covered. 

Why choose us for your Vacation Rental Management?


If you are a current or new owner of a short term/vacation rental, you know how important it is for your listing to stand out from the competition. Having a fresh, vibrant design that appeals to the largest number of renters can give you the competitive edge that you need. With years of  experience in home staging and in the rental industry, the team at Pink Pineapple Properties are experts at knowing how to balance design, durability and homeyness — covering all of your guests needs. Let us do the work, and watch the positive reviews roll in.

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When you book with us you know you are getting a beautifully decorated and maintained property with the most accommodations of any short term rental company in Sarasota.

We look forward to showing you why we are consistently ranked as one of the top vacation rental companies in the Sarasota Florida area.


we dedicate ourselves to the management of your investment through constant hands on communication.


let our experience work for you!

earn more

As Vacation Rental experts we provide professionally decorated, photographed and well written listings which result in more revenue and occupancy than other managed homes.

less stress

We coordinate the cleaning, maintenance, repairs, and stocking of supplies. Your guests get a hotel experience from the exclusivity of your property.

locally owned

Being local gives us a competitive advantage. We know the events, seasons, and trends for the area to maximize bookings.

Great stylish place with a great touch! Very clean and cozy with lots of amenities. Close to Siesta Key and shopping. Courtney and Jon are very reactive to any request. I highly recommend their really cool place overflowing with awesomeness!

- John, April 2020


Bright, cheerful décor. Easy drive to the shoreline. Close to grocery store and shopping. Large pool to do laps in. All the amenities needed to either stay in or dine out were included plus full laundry services.

- Cas, March 2020

We knew it was the perfect place to spend our week vacation as soon as we walked in! Everything was so neat and clean! We never felt not at home all week! There were so many little touches all over that made the entire house picture perfect! There was even a book with pamphlets from different places to go, things to do, and restaurant menus! We definitely will come again!

- Jordan, October 2019


941-313-2097   |   |   Sarasota, Florida 

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