Tim Cranch wearing blue shirt

Tim Cranch

Ellie Penaranda


What do you need to know about buying an investment property in Naples, Florida? Should it be a single family home or a condo? How about annual rental versus a short term vacation rental? Where should you put your money? Firstly, are you a pure investor who will never occupy the property yourself? Are you just looking for a return? Or are you planning on using your “Piece of Paradise” for your own vacations or weekend getaways when your purchase is not occupied by tenants? It is very common in our area to combine your own enjoyment of a home in Naples with covering carrying costs by renting the property for short term vacations.


Naples is a destination that draws real estate investors from around the country and around the world. There are many good reasons that Naples real estate has advantages over other locations and other types of investments.

  • Strong seasonal rental income
  • The option to rent on an annual basis (tenant is paying utilities and most maintenance)
  • Shortage of both seasonal rental properties and annual rental properties – demand is greater than supply
  • Excellent appreciation going forward – single family homes, in particular
  • Naples is easy to get to from anywhere
  • Great weather
  • Pet friendly
  • Top notch beaches with open and convenient access
  • Lots of activities (indoor and out; on and off the water)
  • Restaurants, shopping, galleries, entertainment and nightlife
  • Affordable prices
  • Easy to manage

Click on the links below to sample some good options for seasonal vacation rental properties – these are properties currently on the market for sale. The single family homes are in a neighborhood called Naples Park. It is a community of great interest to anyone with an investor mindset, whether full time rental or a combination of owner occupied / vacation rental, because the homes are walking distance to the beach, affordable and there are no homeowner association restrictions on the number of leases or the length of a lease. Naples Park is transitioning very quickly so prices are on the rise. If you feel it is more suitable in your situation to own a condominium, then Regatta near Vanderbilt Beach is an excellent choice because the location is terrific and the rental policy is as liberal as it gets for condos. It is unique in our area to allow weekly rentals in a condo. As a guideline for buying rental property investments and maximizing the income, homes and condos located west of Route 41 and within walking distance to the beach will garner the best returns and appreciate the most. The closer you are to water and beaches, the more you can charge for rent. Contact us for more information, expected income from a property, operational costs and how / where to make a smart purchase decision. Good investments can come in all different prices ranges – there is something for your budget and goals in Naples.

Single Family Homes in Naples Park

Condos in Regatta

As full time real estate professionals, we represent both buyers and sellers in Naples. If you are a seller, we market your home to local, national and international buyers for the best results. If you are a buyer, we listen well and will find your own “Piece of Paradise” at the best negotiated price and terms.

Tim Cranch at 239-272-4848            Ellie Penaranda at 239-776-5077

TimCranch@StepsToTheBeach.com            Ellie@StepsToTheBeach.com