Vacation Rental Management & Design

About Us

Jon & Courtney Schomburg

Owners

Hi! We are Jon and Courtney Schomburg. Mid-West Natives that moved to sunny Sarasota to pursue our dreams of owning and renting out beautiful beach homes. Courtney is a talented Interior Decorator, Home Stager and Realtor that loves 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. 

Read More

Explore our Amazing Properties

SHORT TERM RENTAL FURNISHING & DESIGN


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.

Learn More

STAY WITH US


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.

See Our Properties

Why choose us for your Vacation Rental Management?

Learn About Our Services

Why Choose Us For Your

Vacation Rental

Manaement

Testimonials

It is hard to find an Airbnb rental that feels like a home - most are decorated to be as sterile and neutral as hotel rooms. This one is charming, warm and it feels like a family cottage that a good friend has lent to you . . . and the owner is very responsive!

Diana, January 2025

Guest

I was faced with an urgent situation and needed a place in downtown Sarasota on a moment's notice. Courtney responded immediately, was able to program the smart lock for me remotely, and I was ensconced within a few minutes of finding the place on the website. Life should be this easy always.

Michael, January 2025

Guest

Courtney was super efficient on response with questions.  If I could give more than 5 stars to Courtney I would.  Place is amazing, immaculate in every way.  Will definitely stay again.

Watha, March 2024

Guest

Contact Us

941-313-2097 |  info@pinkpineappleproperties.com  |  Sarasota, Florida 

Submit your request and we'll get back to you soon with our very best quote.