Buying an Airbnb in Orlando, Florida

The Short Term Shows
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Welcome to the Short Term Shop's specific market series! In each episode of the series we'll be doing a deep dive on a particular aspect of owning/renting an airbnb. Each episode will be hosted by a variety of short term shoppers as well as short term shop agents.

  1. 28 FEB

    2026 Market Update with Mike

    On this week’s episode, Luke Carl dives into the Disney market in Orlando and Kissimmee with Mike from The Short Term Shop, breaking down current inventory trends, pricing shifts, and where real deals can still be found . They discuss how appropriately priced properties are moving, why many 2022 buyers are struggling to sell, and what separates a high-performing, well-themed vacation rental from one that’s leaving money on the table. From million-dollar Story Lake homes to value-add townhomes in Lakaya, the conversation highlights how buying right, financing right, and managing right can still create opportunity in today’s market. how to connect with Mike: mike@theshorttermshop.com     Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://stsplus.com/ Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon Chapters (00:00:02) - Disney Real Estate on Short Term Shop Network(00:00:33) - Real Estate Agent: Orlando, Kissimmee and Disney Market(00:03:49) - $1.1 Million for a High-End Property in Story(00:06:10) - Does this house need a short-term rental?(00:06:51) - 789 Windsor West Side, $699(00:11:05) - $700,000 Windsor West Side home(00:15:41) - 41 West Lakaya, 4 bedroom, 3 bath(00:19:14) - $260,000 Townhome in Disney's Laka Village(00:23:11) - Short Term Business

    24 min

  2. 14/10/2025

    Market Target Update with Mike

    On this week’s episode of the series, Luke Carl sits down with Mike from The Short Term Shop to break down the Disney/Orlando STR scene—why many families look off-property, what Windsor Hills offers, and how to weigh value versus perks. They touch on stabilized pricing and inventory, why clean and well-kept beats expensive over-the-top theming, and how realistic offers are getting accepted (including a recent six-bedroom townhome that closed well under ask). how to connect with Mike: mike@theshorttermshop.com     Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://stsplus.com/ Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon Chapters (00:00:00) - Disney Podcast(00:00:39) - Disney Resort Guest: Rent a House Instead of Staying On Property(00:03:53) - Disney's Windsor Hills Resort and Rent(00:06:30) - Condo vs Townhouse: Should You Buy a Disney Villa?(00:10:03) - Disney Vacation Rentals: Too High(00:15:36) - How to Rent a Disney House(00:16:58) - Wind Windsor Hills Townhouse Sales are Up(00:21:14) - Short Term Rentals for Disney's(00:22:14) - I Think Disney's Theming Has Gone Too Far(00:29:12) - Marathon Man on Spending Money(00:31:56) - Should You Make an Offer on a Home?(00:34:45) - When to Offer a Disney Property?

    40 min

  3. 04/12/2023

    Airbnb Pricing and Calendar Management In Orlando, FL

    In this episode of the series we'll cover pricing and calendar management for your Orlando property. We'll discuss minimum night stays, lead times, who your competition is and why you NEED dynamic pricing software in this market.   Connect with Avery and the Short Term Shop: www.theshorttermshop.com www.strquestions.com Short-Term Rental, Long-Term Wealth Book - https://amzn.to/3Adg6PA Short Term Show and Short Term Rental Management Show - https://linktr.ee/strmshow The Short Term Show - https://linktr.ee/theshorttermshow https://www.facebook.com/groups/shorttermshop https://theshorttermshop.com/cash-flow-calculator/ https://theshorttermshop.com/estimated-returns/ https://theshorttermshop.com/lp/orlando/

    29 min

  4. 01/12/2023

    Common Airbnb Management Occurrences In Orlando, FL

    In this episode of the series we'll cover some common occurrences when owning property in Orlando, Florida. We'll talk about bugs, hurricanes, pools + pool heaters, golf carts, transportation and more.   Connect with Avery and the Short Term Shop: www.theshorttermshop.com www.strquestions.com Short-Term Rental, Long-Term Wealth Book - https://amzn.to/3Adg6PA Short Term Show and Short Term Rental Management Show - https://linktr.ee/strmshow The Short Term Show - https://linktr.ee/theshorttermshow https://www.facebook.com/groups/shorttermshop https://theshorttermshop.com/cash-flow-calculator/ https://theshorttermshop.com/estimated-returns/ https://theshorttermshop.com/lp/orlando/

    25 min

  5. 29/11/2023

    Setting Up Your Airbnb In Orlando, FL

    In this episode of the series we'll be covering the setup process for properties in the Orlando market. We will discuss hiring professionals to get setup, kitchen supplies, catering towards families and kids and more.    Connect with Avery and the Short Term Shop: www.theshorttermshop.com www.strquestions.com Short-Term Rental, Long-Term Wealth Book - https://amzn.to/3Adg6PA Short Term Show and Short Term Rental Management Show - https://linktr.ee/strmshow The Short Term Show - https://linktr.ee/theshorttermshow https://www.facebook.com/groups/shorttermshop https://theshorttermshop.com/cash-flow-calculator/ https://theshorttermshop.com/estimated-returns/ https://theshorttermshop.com/lp/orlando/

    44 min

  6. 27/11/2023

    The Real Estate Contract Process When Investing in Short Term Rentals in Orlando, Florida

    In this episode of the series we'll cover the real estate contract process for Orlando. We'll talk about furniture addendums, typical contingencies, what shows up on home inspections and more.   Connect with Avery and the Short Term Shop: www.theshorttermshop.com www.strquestions.com Short-Term Rental, Long-Term Wealth Book - https://amzn.to/3Adg6PA Short Term Show and Short Term Rental Management Show - https://linktr.ee/strmshow The Short Term Show - https://linktr.ee/theshorttermshow https://www.facebook.com/groups/shorttermshop https://theshorttermshop.com/cash-flow-calculator/ https://theshorttermshop.com/estimated-returns/ https://theshorttermshop.com/lp/orlando/

    51 min

  7. 24/11/2023

    Financing Airbnbs in Orlando, Florida

    In this episode of the series we'll discuss different financing options for properties in Orlando. We'll talk about commercial/portfolio loans, creative options, conventional financing and more.     Connect with Avery and the Short Term Shop: www.theshorttermshop.com www.strquestions.com Short-Term Rental, Long-Term Wealth Book - https://amzn.to/3Adg6PA Short Term Show and Short Term Rental Management Show - https://linktr.ee/strmshow The Short Term Show - https://linktr.ee/theshorttermshow https://www.facebook.com/groups/shorttermshop https://theshorttermshop.com/cash-flow-calculator/ https://theshorttermshop.com/estimated-returns/ https://theshorttermshop.com/lp/orlando/

    30 min

  8. 22/11/2023

    Building Your Short Term Rental Buying Team in Orlando, Florida

    In this episode of the series we'll talk about building your buying team in Orlando! We'll cover how to find an agent, how to find an inspector and more!    Connect with Avery and the Short Term Shop: www.theshorttermshop.com www.strquestions.com Short-Term Rental, Long-Term Wealth Book - https://amzn.to/3Adg6PA Short Term Show and Short Term Rental Management Show - https://linktr.ee/strmshow The Short Term Show - https://linktr.ee/theshorttermshow https://www.facebook.com/groups/shorttermshop https://theshorttermshop.com/cash-flow-calculator/ https://theshorttermshop.com/estimated-returns/ https://theshorttermshop.com/lp/orlando/

    49 min
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Welcome to the Short Term Shop's specific market series! In each episode of the series we'll be doing a deep dive on a particular aspect of owning/renting an airbnb. Each episode will be hosted by a variety of short term shoppers as well as short term shop agents.

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