Tim Cranch wearing blue shirt

Tim Cranch

Ellie Penaranda



Buying a vacation home is both an emotional purchase and an investment opportunity. There is a balance between the human side and the financial aspects to make the right decision. Here are some things to consider when you are thinking about a second home or part time residence in the Naples and Bonita Springs FL areas:

  • How much time are you going to spend here? Will it be a week or two at a time? Will it be a month or more at a time?
  • What time of year will you be in area? 
  • Will you want to rent your home, villa or condo when you are not using it? Your answers to the two questions above play into the equation of the property availability for short term seasonal rentals. Also, any property that is within a community with an HOA is going to have some guidelines on renting. Most condos  restrict rentals to a certain number of leases per year and/or the number of days for a lease. The plus side of renting is that you can cover your carrying costs such as real estate taxes, insurance and association fees.
  • If you decide to rent your property on a short term seasonal basis, should you hire management or go it alone?
  • Think down the road…….will this home purchase become a full time retirement home in a few years?
  • What about resale? Am I buying into a neighborhood which would allow me to sell with a profit if something changes in the future or if I want to move up within the Naples area?
  • Do you want the “lock it and leave it” convenience of condo living?
  • You can easily hire services for a single family home to maintain your residence whether you are here in town or not. Pool service, lawn and yard maintenance and home watch services are all readily available and affordable.
  • Give thought to your activities and daily lifestyle when you are here in the Naples area. Should you be near restaurants and shopping? Should you be smack on the beach? Should you be living in a golf community?
  • Does the home, villa or condo need to be pet friendly?  Most HOA that allow pets for owners do not allow pets for tenants.
  • Should the property be located in a community that is kid friendly?
  • Do you want a boat in the backyard of a canal home or would you keep a boat in a marina?
  • Amenities? Are you likely to take advantage of community amenities or would you prefer not to pay for things you won’t use?
  • Prices have steadily increased in our area as the supply decreases for both single family homes and condos. Would it not make sense to buy now versus later? As time goes on, you can expect to pay more and have less from which to choose.
  • Be wary of any joint ventures with family, friends or associates. These sort of partnerships eventually put stress on relationships.
  • Everyone has a budget for a vacation home purchase. Whether it is $100,000 or $1,000,000 or more, we have the entire spectrum in the Naples and Bonita Springs area. Know your budget, remember to calculate your carrying costs, stay within the budget and share it with your buyer agent representative to get the best results.

Click on the links below for a sampling of opportunities for a great vacation home and a sound investment. 

Naples Condos on the Beach

Naples Condos near the Beach

Naples Single Family Homes near the Beach

Boating – Canal Homes in Naples with Gulf of Mexico Access

Olde Naples Cottages and Single Family Homes

Pelican Bay Single Family Homes

Pelican Bay Villas

Pelican Bay Condos

Barefoot Beach Properties 

Bonita Beach Condos

Naples Park

Golf Communities (Sample of Available Properties)

Bundled Golf Communities (Sample of Available Properties)


Call or e-mail us for a consultation to help you make the best decision that suits your own circumstances.

Tim Cranch at (239) 272-4848   or   TimCranch@StepsToTheBeach.com

Ellie Penaranda at (239) 776-5077   or   Ellie@StepsToTheBeach.com




Pelican Bay Condos for Sale