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#4602671 - 12/13/17 03:13 PM renting out a vacation property
CincyDavid Offline


Registered: 03/03/16
Posts: 704
Loc: Cincinnati, OH USA
I figured short term vacation rentals are a different animal than long term residential rentals, but my bride and I have been toying with buying a condo somewhere between Ft. Myers/Sanibel and Sarasota FL. Anyone have experience with this sort of thing?

I have one friend who only rents to people she knows, another who rents her place through VRBO. Another rents through another service, but the thing that strikes me about him is that every time they use their own house in Destin, he spends every morning cleaning/fixing/painting, then hits the beach in the afternoon.

Part of me thinks it would just be simpler to spend the $1500-2000 a week to rent somebody's else's unit and be done with it.
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#4602679 - 12/13/17 03:21 PM Re: renting out a vacation property [Re: CincyDavid]
pandus13 Offline


Registered: 08/12/11
Posts: 3176
Loc: Chicago,IL,USA
Originally Posted By: CincyDavid
...
Part of me thinks it would just be simpler to spend the $1500-2000 a week to rent somebody's else's unit and be done with it.

Everything is well until HOA fees grow or special assessments appear.
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#4602683 - 12/13/17 03:22 PM Re: renting out a vacation property [Re: CincyDavid]
bubbatime Offline


Registered: 03/18/08
Posts: 5619
Loc: South Florida
Originally Posted By: CincyDavid
I figured short term vacation rentals are a different animal than long term residential rentals, but my bride and I have been toying with buying a condo somewhere between Ft. Myers/Sanibel and Sarasota FL. Anyone have experience with this sort of thing?

I have one friend who only rents to people she knows, another who rents her place through VRBO. Another rents through another service, but the thing that strikes me about him is that every time they use their own house in Destin, he spends every morning cleaning/fixing/painting, then hits the beach in the afternoon.

Part of me thinks it would just be simpler to spend the $1500-2000 a week to rent somebody's else's unit and be done with it.


I have several friends that do VRBO thing in the keys. They. Make. A. KILLING. Thing is, when rich folks go on vacation, they want a really nice, modern, upgraded house. So your buy in just to get the house/condo is going to be at least $600,000 in the Florida keys. But the weekend rents, almost yearly (warm all year), EASILY covers the $600K mortgage, with plenty of money to spare. The entire southwest coast from Clearwater Beach, to Sarasota, to Anna Maria island, Longboat Key, Siesta Key, Boca Grande, Captiva, Sanibel, Pine Island, Naples, Marco Island, and the keys, are EXCELLENT vacation rental locations. You can rent them year round, and they always have a ton of interest.

If its something you are interested in, I think its a good idea. Wife and I will probably go down this path eventually. We are looking at having several vacation rentals and opening a Jet Ski rental business as well.
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#4602684 - 12/13/17 03:24 PM Re: renting out a vacation property [Re: CincyDavid]
walterjay Offline


Registered: 04/12/09
Posts: 234
Loc: Maryland
I thought about doing the same thing a few years back. Chose not to do it and I am glad to not have the hassle. Also, do you always want to go on vacation at the same place all the time?

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#4602687 - 12/13/17 03:26 PM Re: renting out a vacation property [Re: walterjay]
CincyDavid Offline


Registered: 03/03/16
Posts: 704
Loc: Cincinnati, OH USA
Originally Posted By: walterjay
I thought about doing the same thing a few years back. Chose not to do it and I am glad to not have the hassle. Also, do you always want to go on vacation at the same place all the time?


We know several people between Venice and Siesta Key and go out to dinner with them, or boating, etc, so we really are creatures of habit and like to go to the same place. We have been renting the same 2 units (depending on availability) for years.

We tend to go to SK twice a year, Mar/April & November, and one trip elsewhere during the year...Caribbean, Arizona, etc.


Edited by CincyDavid (12/13/17 03:27 PM)
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#4602690 - 12/13/17 03:27 PM Re: renting out a vacation property [Re: CincyDavid]
NormanBuntz Offline


Registered: 07/27/13
Posts: 2120
Loc: Outer Banks, NC
If you're going to treat the condo as a rental property, make sure you brush up on the IRS regulations regarding limitations on your personal use and requirements to take depreciation. The reason your pal works on his rental in the morning is so he can substantiate doing repairs/maintenance/improvements instead of that being a personal use day.

Being a landlord is not for everyone. I did it for 13 years in a resort area and was glad when it ended. PITA rental companies and tenants who always expect the moon.
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#4602694 - 12/13/17 03:29 PM Re: renting out a vacation property [Re: NormanBuntz]
CincyDavid Offline


Registered: 03/03/16
Posts: 704
Loc: Cincinnati, OH USA
Originally Posted By: NormanBuntz
If you're going to treat the condo as a rental property, make sure you brush up on the IRS regulations regarding limitations on your personal use and requirements to take depreciation. The reason your pal works on his rental in the morning is so he can substantiate doing repairs/maintenance/improvements instead of that being a personal use day.

Being a landlord is not for everyone. I did it for 13 years in a resort area and was glad when it ended. PITA rental companies and tenants who always expect the moon.


We have also talked about not renting it at all, but in order for that to work it would have to be a less costly unit, since we wouldn't have any rental income to offset the cost.
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#4602866 - 12/13/17 07:14 PM Re: renting out a vacation property [Re: CincyDavid]
mez Offline


Registered: 11/14/06
Posts: 253
Loc: MA
We rent our 6 bedroom 6 1/2 bath home on Bald Head Island, NC on VRBO since the home was build in 2014. See https://www.vrbo.com/512487. There are not many large homes for rent. We do extremely well. If you have a desirable location it's great way to pay for the cost of ownership and make a few bucks when you are not using it. We are designing on a second rental home on BHI with 7 bedrooms 7 1/2 bath that will sleep over 20 people. We expect this to rent very well also. My wife enjoys interacting with the renters and we have very little renter damage but like I tell my wife everything is repairable. Go for the rental way.
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#4602941 - 12/13/17 08:37 PM Re: renting out a vacation property [Re: CincyDavid]
Sunnyinhollister Offline


Registered: 06/27/09
Posts: 730
Loc: Hollister, CA
We bought an older cabin in the Sierra's a few years ago and rent it out through VRBO: https://www.vrbo.com/781564 . We've put a lot of work into it and we live close enough to drive there. We've also built up list of trusted contractors for the emergencies. The rent we get is enough to cover most of the mortgage and operating expenses. The renters we get are mostly families so we have had a good experience so far. A friend of mine has a rental in an area that caters to a younger crowd and her experience has not been as pleasant.

If you can get someone else to pay for the mortgage why not go for it?
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#4602990 - 12/13/17 09:14 PM Re: renting out a vacation property [Re: CincyDavid]
Mr Nice Offline


Registered: 09/12/04
Posts: 21173
Loc: Orlando, FL
Both you guys have very nice rental properties.

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#4602994 - 12/13/17 09:22 PM Re: renting out a vacation property [Re: CincyDavid]
StevieC Offline


Registered: 08/21/08
Posts: 17116
Loc: Ontario, Canada
My friend rents his gated community house out using VRBO and it's been really great for him. It's rented most of the year to good people.

It's in Florida too!

https://www.vrbo.com/275247




Edited by StevieC (12/13/17 09:24 PM)
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#4603080 - 12/14/17 01:15 AM Re: renting out a vacation property [Re: Mr Nice]
Sunnyinhollister Offline


Registered: 06/27/09
Posts: 730
Loc: Hollister, CA
Originally Posted By: Mr Nice
Both you guys have very nice rental properties.



Thanks!
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#4603738 - 12/14/17 06:02 PM Re: renting out a vacation property [Re: CincyDavid]
Patman Offline



Registered: 05/27/02
Posts: 20335
Loc: Oakville, Ontario
Originally Posted By: CincyDavid


Part of me thinks it would just be simpler to spend the $1500-2000 a week to rent somebody's else's unit and be done with it.


My wife and I are retiring in 2022 and will be spending our winters in southwest Florida from that point on. We briefly toyed with the idea of buying a place and then renting it out for the 8 months we weren't there, but the numbers just don't justify it. Add to that, the nightmare anytime a hurricane rolls through town, I don't need that stress! Instead, we'll probably spend roughly $8-10000 per year to rent for 4 months and when we leave in the spring we don't have to worry about it at all. And if we get tired of one area, we have the freedom to move around too.
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#4604221 - 12/15/17 08:37 AM Re: renting out a vacation property [Re: CincyDavid]
Mr Nice Offline


Registered: 09/12/04
Posts: 21173
Loc: Orlando, FL
Yeah it would be a big mistake to buy if your are only down here for 4 months and not worth the trouble.

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