Make money buying Vacation Rentals | SARASOTA FLORIDA

Lyndsey Ashley
Lyndsey Ashley
Published on December 15, 2020

Buying a vacation rental property is a very exciting possibility. Who doesn’t want to own a second home and make some money while doing it. That is especially true if your next property is a paradise, AKA Sarasota. If you have never done this before, it might seem a bit overwhelming at first, but here’s the good news. I am here today to help you navigate this process. Let’s go over the ins and outs of buying a vacation rental right here in Sarasota, Florida.

So before we begin, consider subscribing to the channel and clicking the little notification bell to be updated of all my new videos and if you are serious about purchasing, selling, or investing here in Florida, you are going to want to stay up-to-date with all my future videos, with all the helpful information I have about the amazing housing market here in the sunshine state. So thanks for subscribing.

Location is everything

If you are going to buy a property for the sole purpose of renting it out, you must think of someone on vacation. What’s in the area? Why do people visit? For Sarasota properties, there are many amenities that bring people back, time and time again. The incredibly beautiful white sandy beaches, rich arts, and cultural community, and numerous golf courses, are just a few of the big ones. And did I mention the weather is absolutely gorgeous. It is Florida after all.

At the end of the day, Sarasota simply has amazing diverse real estate opportunities. You could get a beach front property, if you have got the cash. A Downtown penthouse, a villa on a golf course, or even a cozy starter home. It’s a no-brainer.

Also important to consider are the features of the home itself. Does it have a pool or perhaps a hot tub? What about a fire pit? Will it be pet friendly? All of these features could have an impact on your ability to rent the property out consistently, so you have got to consider it all.

Is this particular property a good investment?

As you peruse the local listings, you might see a property and think like, wow, I’ve hit the jackpot. But hold on for a minute. Did you look at the condo fees? I mean, what about the property taxes and insurance, management fees and general just maintenance? I know this is all the annoying stuff, but if you’ve got to consider it all, these are the things that are going to hit your bottom line, so you need to figure out if it’s worth it for each individual property when you are considering vacation rentals.

Short-term rental restrictions, and other rules

When setting up a property as a rental, there are certain rules you must follow. In Florida, you are required to obtain a license to operate a short-term rental, if renting an entire unit more than three times in a calendar year, for periods of the less than 30 days or a month. So sometimes there will be a city or state ordinance that restricts your ability to rent out a portion or your entire home for even shorter periods of time.

So, in Sarasota, vacation rentals were traditionally required to be booked for at least a week and now if our property owner wants to do short-term rentals on a site like an Airbnb, for example, there are specific taxes that must be paid for those rentals. So, for a complete list of requirements for the area you plan to operate a rental property, you need to check out the local County or even state ordinances.

So as another example, let’s say you buy a property that has a homeowners association attached to it. You will have to follow the rules of the HOA community, otherwise known as the covenants and conditions and restrictions. Basically the rules of your neighborhood can dictate what you are able to do on, or with your property, before you park your car in the street, paint your house, or add a fence even. You’ll have to check the rules and go through the HOA, to see if you can do these things. So you have the HOA, the city, the county, you have some things to check out and those are the real gold mines, are the ones that we don’t have any HOA restrictions. So you make sure you figure that out ahead of time.

Property management

Sometimes, when homeowners choose to rent out a property, they seek the assistance of a property management company. These companies can be very helpful. They usually cover the following: issues with the condition of the property, like cleaning or even repairs. They can even advertise your property. They communicate with perspective renters, on your behalf. They’ll even handle your renter applications, collect your rent, deposit your rent on you, and much more. Some homeowners try to handle these things themselves but for those that do not have the time to deal with running the rental properties, this could be a useful service to consider, especially if you’re doing this from afar.

Know your seasons, maximize your rental profit

Short term vacation rentals have a predictable 12 month cycle, although it is unique to each market. As you do your research, you will see that your market has a peak season and this is where you can really earn some good money with your property. The beauty of Sarasota, Florida, is that you are likely to see multiple times of a year where business is booming.
So our true peak season is around February and April and although you likely also see families vacationing in the summer months in your property, you will may very well book out your weeks in June and July, in advance. And so once you get into August, September and October, it starts to get pretty hot and humid and rentals taper off so much. So school is also back in session around that time, so families have less opportunity to travel. Still, the location offers a wide window of enjoyable vacation time for your tenants.

So, those are my tips for buying a vacation rental in Sarasota, Florida. Have you found the perfect rental property yet? If so, I would love to hear all about it in my comments below. I am Lyndsey Ashley. I’m with Keller Williams Realty Select and if you are looking for a realtor to help you with your next home purchase, or sale, head on over to, and you can schedule a free call with me to talk about your plans to buy, sell, or invest. So contact me today so we can work together to find a home that you love and you can even get a free home evaluation.

Every day I work with people like you who are relocating out of state, especially to Florida. Who do you go to get answers to all your questions? Where do you begin? My goal is to provide answers related to relocating to Florida, the Florida lifestyle, real estate and otherwise. So welcome!

New videos every WEEK – SUBSCRIBE to this channel if you want to learn about real estate, home ownership, or living in SARASOTA – SUBSCRIBE






I am so grateful for all you subscribers, both clients and Realtors, so thanks for watching my videos! Lyndsey is a Sarasota area Realtor with Keller Williams. She loves Sarasota, houses, and helping clients buy and sell real estate.


#LyndseySellsSarasota #ListwithLyndsey #SarasotaFL #Sarasota #Relocation #Florida

DISCLAIMER: All content provided on and the Lyndsey Ashley YouTube channel/social media platforms are for informational/entertainment purposes only. The owner of Lyndsey Ashley social media makes no representations as to the accuracy or completeness of any information on this site or found by following any link on this site. Information provided is subject to change, please consult Lyndsey directly or another licensed real estate agent to receive the best expertise for your specific situation. The owner of Lyndsey Ashley social media will not be liable for any errors or omissions in this information nor for the availability of this information. The owner will not be liable for any losses, injuries, or damages from the display or use of this information.

Relocating to Sarasota?
Download our FREE Relocation Guide!

Let's Talk Real Estate!

label_importantlabel_importantGet A FREE Home Valuation!