Looking to buy a cashflowing vacation home Naples-Sarasota

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LaTarence Dunbar
Lender · Washington DC · Member since 2026 · 65 posts · 16 votes
1mo
Quote from @Sandeep Dhall:

Any recommendations for Naples to Sarasota?




Naples and Sarasota are both strong markets for vacation rentals, but they operate very differently depending on cash-flow goals and local short-term rental (STR) restrictions.

A few key factors to keep in mind for this corridor:

  • Zoning & STR Rules: Sarasota city/county and Naples/Collier County have strict, differing rules on minimum stay durations (e.g., weekly vs. monthly minimums), which directly impact projected occupancy and yield.
  • Property Types: Single-family homes with private pools or condos in non-HOA/investor-friendly communities currently drive the best yields across Sarasota, Venice, and Cape Coral/Naples adjacent pockets.
  • Capital & Acquisition Strategy: Beyond traditional investment property financing, many investors targeting this corridor leverage fast digital equity lines (like Figure) against existing assets to execute cash-like offers or fund down payments quickly without waiting on lengthy traditional underwriting.

I specialize in identifying high-yield coastal opportunities and structuring creative debt/capital packages to maximize cash flow. Sent you a direct message with a couple of specific sub-markets currently delivering the highest cap rates.


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  • Jacob CamhiBusiness Member
    Hinton, WV · Member since 2026 · 131 posts · 40 votes
    1mo

    finding a true cashflowing vacation home in popular florida spots like naples or sarasota is much tougher now with higher prices. the key is less about the general city and more about very specific neighborhoods and local rules.

    i'd start by researching the county and city websites for zoning and short-term rental ordinances in your target areas within naples and sarasota. some areas have strict bans or limits on how often you can rent a place out short-term.

    then, check the rental history and prices on airbnb or vrbo for similar properties (like 2-bedroom condos or 3-bedroom houses) in the specific neighborhoods that actually allow short-term rentals.

    have you already checked for any short-term rental restrictions or transient occupancy taxes in the specific part of sarasota or naples you're looking at?

    1Reply
    • Sandeep Dhall
      OP
      Investor · Austin TX · Member since 2015 · 68 posts · 32 votes
      1mo
      Quote from @Jacob Camhi:

      finding a true cashflowing vacation home in popular florida spots like naples or sarasota is much tougher now with higher prices. the key is less about the general city and more about very specific neighborhoods and local rules.

      i'd start by researching the county and city websites for zoning and short-term rental ordinances in your target areas within naples and sarasota. some areas have strict bans or limits on how often you can rent a place out short-term.

      then, check the rental history and prices on airbnb or vrbo for similar properties (like 2-bedroom condos or 3-bedroom houses) in the specific neighborhoods that actually allow short-term rentals.

      have you already checked for any short-term rental restrictions or transient occupancy taxes in the specific part of sarasota or naples you're looking at?


       I have not checked yet. I run own and run a few Airbnbs in Texas/Georgia. I can check. Are you a realtor in the area?

      1Reply
  • LaTarence Dunbar
    Lender · Washington DC · Member since 2026 · 65 posts · 16 votes
    1mo
    Quote from @Sandeep Dhall:

    Any recommendations for Naples to Sarasota?




    Naples and Sarasota are both strong markets for vacation rentals, but they operate very differently depending on cash-flow goals and local short-term rental (STR) restrictions.

    A few key factors to keep in mind for this corridor:

    • Zoning & STR Rules: Sarasota city/county and Naples/Collier County have strict, differing rules on minimum stay durations (e.g., weekly vs. monthly minimums), which directly impact projected occupancy and yield.
    • Property Types: Single-family homes with private pools or condos in non-HOA/investor-friendly communities currently drive the best yields across Sarasota, Venice, and Cape Coral/Naples adjacent pockets.
    • Capital & Acquisition Strategy: Beyond traditional investment property financing, many investors targeting this corridor leverage fast digital equity lines (like Figure) against existing assets to execute cash-like offers or fund down payments quickly without waiting on lengthy traditional underwriting.

    I specialize in identifying high-yield coastal opportunities and structuring creative debt/capital packages to maximize cash flow. Sent you a direct message with a couple of specific sub-markets currently delivering the highest cap rates.


    1Reply
  • Robert Alpizar
    Real Estate Broker · Naples, FL · Member since 2018 · 40 posts · 24 votes
    1mo

    Hi Sandeep. In Naples, the neighborhood is key to finding a cash flowing property. The City of Naples has strict AirBNB rules while neighborhoods outside of the "City of Naples" is more flexible... I'm a broker in Naples and own a Vacation Rental and Property Management Company... I sent you a message, let's chat.

    1Reply
  • Arman AhmedPro Member
    Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 914 votes
    1mo
    Quote from @Sandeep Dhall:

    Any recommendations for Naples to Sarasota?


    If your main goal is cash flow, I’d definitely give LTRs a look instead of focusing only on vacation rentals. The seasonal market can be attractive, but long-term rentals can offer more consistent income and less turnover/management. I’d also compare the numbers with Midwest markets, where lower acquisition costs can sometimes make the cash flow much stronger for an out-of-state investor.

    [email protected]614-418-6081
    1Reply
  • Vijay FriedmanBusiness Member
    Miami, FL · Member since 2026 · 766 posts · 122 votes
    1mo
    Quote from @Sandeep Dhall:

    Any recommendations for Naples to Sarasota?

    @Sandeep Dhall
    Are you looking for a true STR/vacation rental or more of a seasonal rental? I'd narrow that down first since the cash flow can look pretty different by area and property type between Naples and Sarasota.

    786-656-0387
    DreamPoint Capital
    WebsiteView Page
    1Reply
  • Sarah Vann
    Real Estate Consultant · Charleston, SC · Member since 2024 · 35 posts · 9 votes
    1mo
    Quote from @Sandeep Dhall:

    Any recommendations for Naples to Sarasota?

    With Naples, one thing I highly recommend is to underwrite and consider STR for off season and switching to midterm for snowbird season. It's an opposite strategy compared to most markets but the snowbirds pay top dollar and it's consistent occupancy and minimized expenses :) NOTE: must be Collier unincorporated for true short term. Flamingo Estates and Brookside are generally good places to start. Naqles Park is still pretty inflated but with 4+ beds and amenities with the right management you can do well.

    Sarasota has painful restrictions for STR despite what a lot of agents will claim. There is a little pocket of Sarasota that is in Manatee County called Whitfield Estates - affordable pool homes with the right design and appeal can be amazing! 

    Watch for flood insurance in both. 

    Message me if you have any questions.. I have done a bunch of STR deals in both areas but live in SC now.

    1Reply
  • Lynzie Mackey
    Fort Myers, FL · Member since 2015 · 37 posts · 7 votes
    1mo

    There's a lot of opportunity in the Fort Myers area. I live and own on Fort Myers Beach. A lot of whether the property will cashflow will be dependent on design, amenities and management.  Our condo market on the island has a ton of inventory right now and the whole Island is rebuilding from a major storm 4 years ago. It's a great opportunity zone. 

    1Reply
  • Nick EdgingtonPro Member
    Real Estate Broker · Bradenton, FL · Member since 2021 · 5 posts · 0 votes
    1mo
    Quote from @Sandeep Dhall:

    Any recommendations for Naples to Sarasota?


     Hi Sandeep, I am a local broker in Sarasota market. What kind of property are you looking to purchase? What is your buy box? I may be able to help if we can dial in what exactly you are looking to purchase. 

    0Reply
  • Noah Fischer
    Investor · Tampa · Member since 2026 · 8 posts · 3 votes
    1w

    Hi Sandeep,

    My family operates vacation rentals on Anna Maria, Longboat & Sarasota, so this is our home corridor.

    Most of the thread is on the revenue side: where you can legally rent short-term, and what yields. Worth pressure-testing the cost side too. The one that gets out-of-state buyers most often is property tax. The number on a listing is the seller's. Florida re-assesses at full market value the January after you close, so the real bill doesn't land until your second year, and if the seller held the place a while it's a big step up. No homestead on a second home to soften it. Sarah's flood comment is the same problem on the insurance line.

    I'm based in Tampa and building a tool that pulls Florida public records to help assess carrying costs. If you tell me what you're looking at (area, price band, or even better a specific address) I can pull the records and tell you what I find. No cost or catch, the tool is in development and I'm just looking for real deals to run it against in the area. Happy to talk through what operating there is actually like, too.

    0Reply
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