Late Starter - 2nd Property -First STR in San Antonio — 3BR Near Lackland AFB

San Antonio, Texas
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Late Starter - 2nd Property -First STR in San Antonio — 3BR Near Lackland AFB

Freddy Aguirre
Member since 2025 · 19 posts · 9 votes

Hey BP fam,

Excited to finally share this one — I just picked up a 3BR/1BA short-term rental in San Antonio, TX that sleeps 6. I'm on my 2nd guest stay so far. It's sitting in a great spot: about 3 miles (7 min) from Lackland AFB and 6.5 miles (11 min) from Sea World, so I'm hoping to capture both military-family traffic (PCS moves, TDY stays, family visits) and the tourist crowd hitting Sea World and the River Walk area.

This is my second property overall (I've got a long-term rental in Conroe), but my first venture into the STR/Airbnb world, so I'm equal parts thrilled and aware of how much I don't know yet. I'd genuinely love to tap into the collective brainpower here before I get too far down the road.

A few things I'd love input on:

  • Design/furnishing for a mixed audience — has anyone else furnished for both military relocations and vacation travelers? Do you lean more "functional/extended-stay" or "fun vacation vibe," or is there a sweet spot?

  • Lackland AFB proximity — anyone had success (or lessons learned) marketing an STR near a military base? Curious about seasonality tied to PCS season, TDY orders, etc.

  • Pricing/comp strategy — how are you all handling dynamic pricing tools (PriceLabs, Wheelhouse, etc.) for a market like SA that has both steady demand (military) and seasonal spikes (tourism)?

  • Property management — using Hospitable at this point.

I'm treating this one as a big learning project as much as an investment, so please don't hold back — tell me what you wish someone had told you before your first STR. Mistakes, wins, horror stories, all welcome!

Thanks in advance, BP community — looking forward to learning from you all as I get this one up and running. 🙌

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Gavin PehlPro Member
Member since 2025 · 4 posts · 3 votes
1w

We do do STR as investments it we stay in them. I think there is a lot of good advice on here for what you could improve. The hardest one to change but the one I agree is I biggie is the one bathroom. Time will tell if that matters in your market but we would look for a place with more than one bathroom eve though you have done such a great job on the rest of the house

I love the bathroom hospitality area. You really did that well I think. The vibe is welcoming and light. The finishes are well done and clean. best of luck to you. 

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  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    1w

    Congratulations! I found it to be a fairly significant learning curve going from LTR to STR but it has been ok overall especially because I'm using mine as personal vacation spots also. If you post a link I'm sure you would garner some valuable design advice. The thing that stuck out to me, and maybe it is just a me thing, is the 1 bathroom. Even when traveling as a couple I won't consider anything less than 1.5 bathrooms.

    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      1w

      Great point about the bathroom. I thought the same thing. I'm hoping to use some profit to help supplement a master on suite addition down the line. There is a great spot for it towards the back of the house. Based on the AirDNA data it could add about $75 per night. Plus it sure would help if I ever decide to sell it!

      0Reply
  • Freddy Aguirre
    OP
    Member since 2025 · 19 posts · 9 votes
    1w

    Thabk you and great point. Here is the link and also added to the post. airbnb.com/h/brownleaf-ehp

    1Reply
  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    1w

    It is really cute! Pics are good although, and truth be told not my area of expertise, I would drop the 2nd living room pic and the pink bedroom to include bathroom and an exterior shot in the initial cluster? Only other thing and I suspect this may be geographic is the chain link fence. Privacy fences are expensive and may not be worth the outlay but in my area the only places you see chain link is class C and D neighborhoods. Look forward to hearing what others say and watching your business flourish.

    1Reply
  • Freddy Aguirre
    OP
    Member since 2025 · 19 posts · 9 votes
    1w

    Thank you for your feedback. I really appreciate it.

    1Reply
  • Lauren Kormylo
    Rental Property Investor · Phoenix, AZ and Rehoboth Beach DE · Member since 2019 · 1k+ posts · 1k+ votes
    1w

    Your house is very cute and stylish! A few things that I would suggest:

    I don't see a dining room or table? Did you forget to put a pic of it in there?

    Your sofa seats 3 or maybe 4, but you sleep 6. I would remove the plant and put in 2 more chairs. The puff isn't good seating for watching TV.

    The beds that sleep 2 people really should have nightstands on both sides. Everyone needs a place to put their phone + charger, glasses, drink, etc. And I like having a lamp on both sides.

    People today like to live out of their suitcases for short trips of 1 to 5 days, so they appreciate luggage racks in the bedrooms so they don't have to put their open suitcases on the floor. Amazon has them.

    The cracks in the concrete back patio are so large, I'm afraid it might be a tripping hazard, especially for someone in heels. If a heel were to sink down in there or catch on it, a woman could easily twist her ankle and fall.

    I agree with Jules on the photos. Your first 5 pics are what someone sees when they pull up your listing. I would only have one of the living room in there, and add the bathroom for sure, and an exterior.

    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      1w

      Thank you for your feedback. Yes I need to update the photos to show the kitchen table and luggage racks. Great call on the nightstands.

      1Reply
  • Michael Eskenasy
    Investor · Pacific Northwest · Member since 2026 · 538 posts · 300 votes
    1w
    The biggest thing I’d avoid is treating this like one STR with one demand curve. You really have two businesses in the same house: Lackland-driven stays and San Antonio leisure. I’d furnish toward durable, clean, extended-stay functionality first—good beds, real workspace, luggage/storage, washer/dryer setup, blackout curtains, kitchen that can actually support a family—then layer enough personality on top that it still photographs well for vacation traffic. Don’t theme it so hard that military families feel like they’re staying in an Airbnb gimmick. Same with pricing: I wouldn’t use one static comp set. Track Lackland graduations/PCS/TDY demand separately from weekends, holidays, SeaWorld, conventions, etc. Those signals will move differently. Hospitable is plenty to start. Your bigger advantage will come from building a tight turnover/maintenance/vendor process now, before volume exposes the gaps. This is exactly the kind of operating problem I spend a lot of time looking at. Feel free to reach out if you want to compare notes once you have a few more stays under your belt.
    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      1w

      Great advice. I'm working on my backup team as we speak. Cleaners, handyman, and landscaper have been great so far but I have gaps in the operation without the backup. Love all the great advice from everyone so far.

      0Reply
  • Freddy Aguirre
    OP
    Member since 2025 · 19 posts · 9 votes
    1w

    And thanks for the offer. I would love to compare notes after a few more stays.

    0Reply
  • Divin KanyamaBusiness Member
    Accountant · Seattle, WA · Member since 2025 · 202 posts · 65 votes
    1w

    Congrats on the new property and your first two stays, @Freddy Aguirre . With Lackland and SeaWorld nearby, I’d create a comfortable extended-stay setup—strong Wi-Fi, laundry, workspace, storage, and a stocked kitchen—with a few San Antonio touches for vacation guests. Use dynamic pricing as a guide, not autopilot, and track occupancy and net revenue closely. My biggest advice: treat it like a hospitality business, keep reliable cleaning and maintenance backups, build reserves, and track it separately from your Conroe rental so you know the true cash flow after every expense.

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    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      1w

      Thank you for the sound advice. I appreciate it.

      0Reply
  • Gavin PehlPro Member
    Member since 2025 · 4 posts · 3 votes
    1w

    We do do STR as investments it we stay in them. I think there is a lot of good advice on here for what you could improve. The hardest one to change but the one I agree is I biggie is the one bathroom. Time will tell if that matters in your market but we would look for a place with more than one bathroom eve though you have done such a great job on the rest of the house

    I love the bathroom hospitality area. You really did that well I think. The vibe is welcoming and light. The finishes are well done and clean. best of luck to you. 

    2Reply
  • Freddy Aguirre
    OP
    Member since 2025 · 19 posts · 9 votes
    1w

    Thank you for the feedback. The bathroom addition is definitely a priority.

    0Reply
  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    1w

    Congrats! I have some properties near MacDill AFB but I think each base will have their "seasons" as I know Lackland is AF basic training so you will have families coming to visit etc and MacDill although an AFB has large joint components with CENTCOM and SOCOM. I would just recommend to build your compset and mind the data with influx of searches in the area will point to higher pricing opportunities. Good luck!

    [email protected]813-563-0877
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    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      1w

      Thank you for your feedback. I purchased AirDNA and watching some videos in how to properly use it. I appreciate the advice.

      0Reply
  • Akash Kakumani
    Member since 2020 · 9 posts · 2 votes
    1w

    Hey Freddy! Congratulations on the purchase. When choosing an amenity I discovered airroi which I like to use. Especially the amenities view: https://www.airroi.com/atlas/charts/amenities?country-code=US&state=Texas&city=San-Antonio&neighborhood=78227 based on this, I see that catering towards children (pack n play, board games, etc) will likely move the needle for you. I also noticed if I specified 1 bathroom that I didn't see any comparables on the platform. That should be an immediate callout to what other's have mentioned that adding another bathroom is critical.

    I'd love to stay in touch and chat about your journey as you get ramped up! I just launched 2 airbnb's myself the last 2 years so I'm semi new to the space. Would love to learn together!

    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      1w

      Thank you for the information. I will be sure to check out airroi. Yes let's stay in touch, I would love to be able to bounce ideas off other fellow investors.

      0Reply
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    1w

    Freddy, for a first STR I'd focus less on trying to appeal equally to every guest type and more on who you realistically expect to book the property most often.

    With military relocations, visiting families, TDY stays, and tourism all potentially in the mix, I’d probably lean toward a clean, durable, comfortable setup that works well for longer stays, then add enough personality that it still photographs well for vacation travelers. Good beds, blackout curtains, reliable Wi-Fi, work space, parking, laundry, and a functional kitchen may matter more than loading the house up with novelty amenities.

    For pricing, I’d avoid setting one strategy and forgetting it. I’d review your true comp set regularly by bedroom count, guest capacity, location, quality, and amenities, then watch how the property performs during military demand periods versus tourism peaks.

    From the tax side, this first year is important. I'd track average guest stay, your own participation hours, cleaner/co-host/manager hours, furnishing and improvement costs, and the placed-in-service date from day one. If you're hoping to use STR losses against W-2 or other active income, the average-stay and material-participation rules need to line up.

    And if you rely on the 100-hour-and-more-than-anyone-else material participation test, make sure you can reasonably track the hours of cleaners and anyone else working on the property too.

    Since you already have an LTR, I'd also look at both properties together from a tax-planning standpoint rather than treating the STR as a completely separate investment.

    Feel free to DM me, I'd be happy to send over a few STR tax resources that might be helpful.

    [email protected]941-914-7779
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    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      1w

      Wow! Tons of great information and you hit my strategy right on the head. I'm tracking my hours, cleaners and handy man on toggle. It's been way more hours in the front end than I thought but it will help with my strategy. We're focusing in the military stays and love the feedback on clean and comfortable. Thank you so much for the information.

      0Reply
  • Garrett Wagner
    Member since 2026 · 1 post · 1 vote
    1w

    Congrats on getting the first STR up and running! One thing I'd definitely make sure you handle early is confirming the property is properly insured for short-term rental use and not just sitting on a standard homeowners or long-term landlord setup.

    With guests already staying there, that’s one of those things that’s much better to verify before a claim than after one. 

    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      2h

      Thank you, I actually went through steadily.

      0Reply
  • Matthew Tregoning
    Real Estate Consultant · Melbourne, FL · Member since 2019 · 225 posts · 116 votes
    3h

    Air Force vet here. For families visiting Lackland I'd keep the base's official visitor-info link in the guidebook, along with clear parking and arrival instructions. Let them check the current requirements there. One less thing to dig around for while they're trying to get everybody out the door.

    1Reply
    • Freddy Aguirre
      OP
      Member since 2025 · 19 posts · 9 votes
      2h

      Thanks for the feedback and great tip. I'll be sure to add it to my digital guide.

      0Reply
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