Where and When to Look for Vacation Rentals

by AJ Pettersen · 6 comments

My fiance and I are ‘moving’ to Florida in January, but the move may only last through March. This presents a unique opportunity, because we can look for vacation rentals in the area. Apartments can only be rented for a minimum of 7 months in Florida and furnishing would be too expensive for the short time period. So where do we look? And when do we start?

Length of Stay

Our length of stay is more in line with vacationers than people who are moving for work purposes, as it is common for vacationers to take vacations anywhere from a few days to a few weeks. Along this spectrum there are different options for places to stay, of course: 

A hotel may be your best option if your stay will be less than a week. This will also depend on how many people will be along for the trip. Can you find a hotel room to fit a large family? Or is it just you and your significant other? A per night price may be most reasonable for a short stay. Don’t forget about the hotel discount codes that show up online every once in a while too.

If you are planning on staying a week or longer, you may want to look for a place that charges by the week. These can be found in a number of different locations, such as Craigslist.com and VRBO.com. You can set your preferences and should be able to find a place to fit your needs.

If you are in a unique situation like my fiance and I, you will want to find a place that appeals to visitors of at least a month. We do most of our searches using Craigslist and local real estate rental companies. It has been a difficult search thus far, but we are confident we will find the right place.

Keep in mind the season you vacation will largely affect the cost of your stay. Staying down south in-season (usually November through March) will cost more than twice as much as the other months. This is especially true for furnished rentals lasting more than a month.

When to Start Looking

Your search for vacation rentals needs to begin a long time before your trip. If you are planning on staying at a hotel, you have a little more time, but finding a room with sufficient space and the right amenities is important.

My fiance and I have already started looking for a place to stay, but we won’t be heading south for another 5 months. If you are planning your trip during the winter months there will be a number of other people planning on doing the same. You would rather be early than late in your search.

What’s Your Plan?

You should make a list of things you want in your rental. How long will your stay be? Do you want a private pool? Near the water? The more amenities you want, the earlier you will need to begin your search.

How do you go about searching for vacation rentals? Do you have any tips for my search?

Disclaimer: On my search on Craigslist, I have run into a few scams. Be careful while searching, and make sure you are dealing with a credible renter.

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  • Shane says:

    I used to live in Florida and the info you are getting may be wrong. You will be moving in January which will make it harder to find a decent priced place cause it is high season there then and many Canadians and northerners have migrated south for the winter. If you let us know where you are trying to move It might help. If you are staying on the east coast of Florida, a rule of thumb is to look east of Highway 95. The further north you go the more reasonable prices will be. More info is needed to help you with your search.

  • Persepone says:

    Once upon a time I had a 3 month job in Boston, MA and the rents there are outrageous! I found a campground on a commuter rail line and packed up my tent, sleeping bag, other camping paraphenalia and went camping for 3 months. I did have to change tent sites weekly to avoid the problem of not appearing to “live” there for 3 months, but moving a tent is pretty simple. The campground had all sorts of amenities, including a pool… So in the morning I went off to work on the commuter train and in the evening I got off the train, and within minutes was changed into a bathing suit and in the pool. I’m guessing this would work even better with an RV–but actually it worked fine for me with a tent… I have very happy memories of that summer…

  • herbert says:

    I am a long time fan of RV’s. For the price you would spend on the vacation rental, you could purchase a clean used unit, and then have something to show for your money at the end of your stay.

  • Marjorie says:

    It’s not true that you can only rent apartments in Florida for a minimum of 7 months. MANY are available month to month. There is a huge inventory of vacant properties including homes that are furnished. Winter is considered high season but still you shouldn’t have much problem finding a place. I’d suggest finding a local paper for the town you are going to and seeing what those ads say. Otherwise you will be paying top dollar for those rentals.

  • Lance @ Money Life and More says:

    I live in a beach tourist town in Florida and the snow birds come down for the winter because they can get some great deals on the beach front condos. Too cold to go in the water so our town tends to be pretty quiet in the winter months.

  • Marbella says:

    I am a real estate broker, and we do rentals. 70% of our customers come through recommendations from other satisfied customers. So my advice is to ask friends and relatives if they can recommend a broker for you.

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