best practices for 3 month lease

Killingworth, CT · Member since 2014 · 24 posts · 11 votes

Hi, I'm new to the FLA STR market, previously I self managed a 2 family unit in CT for 10yrs. I have a condo that I am leasing for a 3 month minimum in a nice small town a mile from the beach. I am looking for some best practices regarding the lease.

Do most STR require 30% down and final payment before the stay? Then all 3 of the following: security deposit, renters insurance and damage insurance? For most STR's, is an inspection checklist conducted? Do most STR tenants pay a departure cleaning fee? Do any STR tenants pay utilities?

Any guidance you can provide or suggestions to helpful material is greatly appreciated.

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John UnderwoodPro Member

Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes

11mo

Quote from @Kathryn Lauterbach-Bell:

Any guidance you can provide or suggestions to helpful material is greatly appreciated.

I treat it the same as a 1 week stay. They pay 100% up front.

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Andrew SteffensBusiness Member
Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
11mo
Hi Kathryn congrats on being here in the sunshine state! I am an active member of the community in the Tampa/St Pete metro as well.
This question sort of depends on how you are marketing. The big OTA's like Abnb and VRBO have their own payment options for the guests. Since you are doing 3 month leases this is more of a MTR set up and if you are finding your guests via Zillow or Furnished Finder, etc you can set the terms. I do some MTR's but usually through OTA's. I would see what your competition is doing and emulate it or improve it from a guest POV so you remain competitive.
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John UnderwoodPro Member
Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
11mo
Quote from @Kathryn Lauterbach-Bell:

Hi, I'm new to the FLA STR market, previously I self managed a 2 family unit in CT for 10yrs. I have a condo that I am leasing for a 3 month minimum in a nice small town a mile from the beach. I am looking for some best practices regarding the lease.
Do most STR require 30% down and final payment before the stay? Then all 3 of the following: security deposit, renters insurance and damage insurance? For most STR's, is an inspection checklist conducted? Do most STR tenants pay a departure cleaning fee? Do any STR tenants pay utilities?
Any guidance you can provide or suggestions to helpful material is greatly appreciated.

I treat it the same as a 1 week stay. They pay 100% up front.
2 Reply
- Kathryn Lauterbach-Bell
  OP
  Killingworth, CT · Member since 2014 · 24 posts · 11 votes
  11mo
  Quote from @John Underwood:
  
  Quote from @Kathryn Lauterbach-Bell:
  
  Hi, I'm new to the FLA STR market, previously I self managed a 2 family unit in CT for 10yrs. I have a condo that I am leasing for a 3 month minimum in a nice small town a mile from the beach. I am looking for some best practices regarding the lease.
  Do most STR require 30% down and final payment before the stay? Then all 3 of the following: security deposit, renters insurance and damage insurance? For most STR's, is an inspection checklist conducted? Do most STR tenants pay a departure cleaning fee? Do any STR tenants pay utilities?
  Any guidance you can provide or suggestions to helpful material is greatly appreciated.
  
  I treat it the same as a 1 week stay. They pay 100% up front.
  
  Thank so much for your responses, very helpful.
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Carolyn Fuller
Cambridge, MA · Member since 2015 · 651 posts · 736 votes
11mo
I require last month rent upon the signing of a lease and monthly rent on the first day of the month for the other months. I do not require a security deposit or any insurance. I do not provide an inspection checklist. I treat my tenants the same way I treat my STR guests. All they need to bring are their clothes and their laptop. All they need to do upon check out is to lockup and text me. I provide all utilities and a monthly cleaning service, all of which are covered by their monthly rent payments. In other words, there are no fees beyond their monthly rent.
In my market, people who are renting for 3 months want all that an STR would provide and no additional fees. I throw in a monthly cleaning service to remind them that I am taking care of my rental and expect them to do so, as well.
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Hunter Loomis
Real Estate Agent · Tampa · Member since 2025 · 17 posts · 6 votes
9mo
Hi Kathryn!
Sorry I am little late to the party here, but I see you're a fellow Realtor that moved from CT to Florida.
Here's my 2 cents:
Most Florida short-term rentals typically require an upfront payment of 25–50% at booking and the full balance due before arrival, along with either a security deposit or a damage waiver, but not usually both plus renters insurance. Hosts commonly use a check-in/out inspection checklist and charge a departure cleaning fee, which guests generally expect. Utilities are almost always included unless the stay exceeds 30–60 days, in which case some owners bill electricity separately.
Hope this helps!
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