Struggling to Pick My First STR Market
Most Popular Reply
Real Estate Agent · Louisiana · Member since 2017 · 214 posts · 146 votes
8moThis is something that will be personal to you. I would suggest finding a local market near your main base to jump in. Doesn't have to be a slam dunk on AirDNA. My first market is 45 minutes away, we had a little 1 bedroom condo in an older historic town (population under 2,000). Condo just did nearly 25% of its purchase price in revenue in 2025. This towns numbers aren't great on AirDNA at all but I noticed a bunch of the listings weren't "professional" looking. Good photos & description, consistent reviews & its been a hidden gem. Don't over complicate it.
24 Replies
- Real Estate Agent · Louisiana · Member since 2017 · 214 posts · 146 votes8mo
This is something that will be personal to you. I would suggest finding a local market near your main base to jump in. Doesn't have to be a slam dunk on AirDNA. My first market is 45 minutes away, we had a little 1 bedroom condo in an older historic town (population under 2,000). Condo just did nearly 25% of its purchase price in revenue in 2025. This towns numbers aren't great on AirDNA at all but I noticed a bunch of the listings weren't "professional" looking. Good photos & description, consistent reviews & its been a hidden gem. Don't over complicate it.
- Investor · Member since 2024 · 11 posts · 4 votes8moI live in San Luis Obispo, CA which is a HCOL place so don’t have many options nearby unfortunately.
Quote from @Josh Ball:
This is something that will be personal to you. I would suggest finding a local market near your main base to jump in. Doesn't have to be a slam dunk on AirDNA. My first market is 45 minutes away, we had a little 1 bedroom condo in an older historic town (population under 2,000). Condo just did nearly 25% of its purchase price in revenue in 2025. This towns numbers aren't great on AirDNA at all but I noticed a bunch of the listings weren't "professional" looking. Good photos & description, consistent reviews & it’s been a hidden gem. Don't over complicate it.
- Member since 2022 · 29 posts · 23 votes8mo
I picked my first one in the Catskills because its close to where I live in NYC. Was it the best deal ever? Definitely not but it helped me learn this game a lot better. Where do you live? I'm sure there is a popular destination close by where you can manage the property and get a feel for whether you like this or not. Your budget matters. A lot of places wont pan out if you are going in cheap, you need to spend on design, furniture, amenities etc.
- Investor · Member since 2024 · 11 posts · 4 votes8moI live in San Luis Obispo, CA but I’m from Long Island, NY which is why I was interested in the Catskills too! I’m worried if the property is too expensive then it won’t cash flow even with amenities especially in a popular place with lots of competition. Do you think the Catskills are oversaturated now? I did find some properties on Zillow. I can go up there, connect with an agent and check out some properties!
Quote from @Michael Lipari:
I picked my first one in the Catskills because it’s close to where I live in NYC. Was it the best deal ever? Definitely not but it helped me learn this game a lot better. Where do you live? I'm sure there is a popular destination close by where you can manage the property and get a feel for whether you like this or not. Your budget matters. A lot of places wont pan out if you are going in cheap, you need to spend on design, furniture, amenities etc.
- Member since 2022 · 29 posts · 23 votes8mo
Quote from @Fizza Ali:
I live in San Luis Obispo, CA but I’m from Long Island, NY which is why I was interested in the Catskills too! I’m worried if the property is too expensive then it won’t cash flow even with amenities especially in a popular place with lots of competition. Do you think the Catskills are oversaturated now? I did find some properties on Zillow. I can go up there, connect with an agent and check out some properties!Quote from @Michael Lipari:
I picked my first one in the Catskills because it’s close to where I live in NYC. Was it the best deal ever? Definitely not but it helped me learn this game a lot better. Where do you live? I'm sure there is a popular destination close by where you can manage the property and get a feel for whether you like this or not. Your budget matters. A lot of places wont pan out if you are going in cheap, you need to spend on design, furniture, amenities etc.
I would say the Catskills market is pretty saturated but not as much as other nearby spots like the Poconos. I wouldn't necessarily just view random properties from zillow. Id recommend paying for a software like AirDNA to get a better view of how properties might perform. Then I would look at actual numbers of similar properties by going on platforms like AIRbnb and seeing how many days those properties are actually booking for. Also find a realtor who has helped people buy Short term rentals in the area. After all of that you'll have a better idea what to purchase.
- Investor · Member since 2024 · 11 posts · 4 votes8moYup! I’ve been doing all that. I think I’m interested enough to reach out to a realtor in that area and get some more info. Thank you for your help!
Quote from @Michael Lipari:
Quote from @Fizza Ali:
I live in San Luis Obispo, CA but I’m from Long Island, NY which is why I was interested in the Catskills too! I’m worried if the property is too expensive then it won’t cash flow even with amenities especially in a popular place with lots of competition. Do you think the Catskills are oversaturated now? I did find some properties on Zillow. I can go up there, connect with an agent and check out some properties!Quote from @Michael Lipari:
I picked my first one in the Catskills because it’s close to where I live in NYC. Was it the best deal ever? Definitely not but it helped me learn this game a lot better. Where do you live? I'm sure there is a popular destination close by where you can manage the property and get a feel for whether you like this or not. Your budget matters. A lot of places wont pan out if you are going in cheap, you need to spend on design, furniture, amenities etc.
I would say the Catskills market is pretty saturated but not as much as other nearby spots like the Poconos. I wouldn't necessarily just view random properties from zillow. Id recommend paying for a software like AirDNA to get a better view of how properties might perform. Then I would look at actual numbers of similar properties by going on platforms like AIRbnb and seeing how many days those properties are actually booking for. Also find a realtor who has helped people buy Short term rentals in the area. After all of that you'll have a better idea what to purchase.
- 8moKenneth GarrettPro MemberInvestor · Florida Panhandle/Illinois · Member since 2016 · 4k+ posts · 3k+ votes
I used the Short Term Shop for my first STR. @Avery Carl has a brokerage firm that covers multiple states and she also wrote a couple books on the topic. They are very helpful. "Short Term Rental Long Term Wealth" and "Smarter Short Term Rentals". My first one was out of State in Florida while I lived in the Chicago area. Spent three weeks getting it ready and picking a cleaner and handyman. I self manage it. It was a great buy.
Best of Luck.
- Investor · Member since 2024 · 11 posts · 4 votes8moI’ve been avoiding Florida because of high insurance costs. But this is helpful! Thank you so much. Will check it out! I want to self manage for the first year for the tax benefits.
Quote from @Kenneth Garrett:
I used the Short Term Shop for my first STR. @Avery Carl has a brokerage firm that covers multiple states and she also wrote a couple books on the topic. They are very helpful. "Short Term Rental Long Term Wealth" and "Smarter Short Term Rentals". My first one was out of State in Florida while I lived in the Chicago area. Spent three weeks getting it ready and picking a cleaner and handyman. I self manage it. It was a great buy.
Best of Luck.
- 8moJeremy TallmanBusiness MemberProperty Manager · Indianapolis, IN · Member since 2016 · 142 posts · 75 votes
We're happy to advise you on buying in North Indy. One thing to keep in mind... both Carmel and Fishers (not north Indy, but suburbs to the north) have rent caps, so buying to rent is super hard there.
Feel free to message me, and good luck!
T&H Realty Services, Inc.4.41266 Reviews- Investor · Member since 2024 · 11 posts · 4 votes8moThank you so much! I didn’t know that. I also want LTR to be a reasonable option as an exit strategy if needed so it’s useful information. I was specifically looking at Butler Tarkington.
Quote from @Jeremy Tallman:
We're happy to advise you on buying in North Indy. One thing to keep in mind... both Carmel and Fishers (not north Indy, but suburbs to the north) have rent caps, so buying to rent is super hard there.
Feel free to message me, and good luck!
- 8moAndrew SteffensBusiness MemberTampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
With 50 states it can be overwhelming. Most traditional markets like Orlando or Gatlingburg (and maybe Joshua Tree?) are oversaturated. Most other popular markets are competitive at the least. I cannot speak all markets and not even my entire state, but I can say there is still positive cash flow to be found in Tampa, FL metro :)
Vacation Rentals of Florida53 Reviews - Memphis, TN · Member since 2024 · 180 posts · 223 votes8mo
Hi @Fizza Ali
Welcome to BP!
Have you taken a look at Memphis? The barrier to entry is very low, rent-to-price ratios are high, and I have worked with countless new investors that have gotten started in our market recently. Check out the Investors Guide To Memphis Real Estate wherever you find your podcast and just watch one or two of those videos. My team lead, Dean Harris and my broker, Douglas Skipworth lay out boots on the ground knowledge every week on how you can get started as a new investor in Memphis or scale in Memphis as a seasoned investor. I'm happy to hop on a call and give you some more info on how we can get you off to a good start and set up your team. Let's talk soon.
Best of luck!
- Investor · Member since 2024 · 11 posts · 4 votes8mo
Quote from @Allie McAlister:
Hi @Fizza Ali
Welcome to BP!
Have you taken a look at Memphis? The barrier to entry is very low, rent-to-price ratios are high, and I have worked with countless new investors that have gotten started in our market recently. Check out the Investors Guide To Memphis Real Estate wherever you find your podcast and just watch one or two of those videos. My team lead, Dean Harris and my broker, Douglas Skipworth lay out boots on the ground knowledge every week on how you can get started as a new investor in Memphis or scale in Memphis as a seasoned investor. I'm happy to hop on a call and give you some more info on how we can get you off to a good start and set up your team. Let's talk soon.
Best of luck!
Thank you!! Will send you a message!
- Member since 2019 · 1k+ posts · 292 votes8mo
The market just matured, so it takes more nuance now than it did a few years ago. I’d stop chasing “top markets” and instead focus on what actually drives demand. A lot of the best first deals aren’t in sexy destinations but in secondary or tertiary markets with steady travel tied to hospitals, universities, events, or corporate travel.
- Investor · Member since 2024 · 11 posts · 4 votes8moYup! That’s how I ended up with Indianapolis!
Quote from @Andrew Street:
The market just matured, so it takes more nuance now than it did a few years ago. I’d stop chasing “top markets” and instead focus on what actually drives demand. A lot of the best first deals aren’t in sexy destinations but in secondary or tertiary markets with steady travel tied to hospitals, universities, events, or corporate travel.
- Interior Decorator · Northern Indiana · Member since 2023 · 8 posts · 2 votes8mo
For insights about the STR market in Indy, I'd recommend reaching out to Tyler Lingle with Roots Realty in Indianapolis—Roots specializes in helping investors and Tyler would be a good realtor to have a resource as you consider if that location would be the right fit for you!
Side note—my sister and I run a one-stop-shop creative studio for STRs—including interior design, murals, branding, and direct booking websites to help hosts stand out. As things progress, feel free to reach out if those are things you're looking to hand off to someone else!
- Rental Property Investor · San Diego, CA · Member since 2019 · 28 posts · 10 votes8mo
@Fizza Ali We invest in indy market for 6 years now and have LTRs, MTRs, and STRs all across the place. We own about 7 STRs and manage about 5 STRs for our investors. Feel free to ping me with any questions.
- Rental Property Investor · San Diego, CA · Member since 2019 · 28 posts · 10 votes8mo
Quote from @Olivia Feller:
For insights about the STR market in Indy, I'd recommend reaching out to Tyler Lingle with Roots Realty in Indianapolis—Roots specializes in helping investors and Tyler would be a good realtor to have a resource as you consider if that location would be the right fit for you!
Side note—my sister and I run a one-stop-shop creative studio for STRs—including interior design, murals, branding, and direct booking websites to help hosts stand out. As things progress, feel free to reach out if those are things you're looking to hand off to someone else!
I would love to connect with you and your sister regarding designing. Thank you
- Interior Decorator · Northern Indiana · Member since 2023 · 8 posts · 2 votes8mo
Quote from @Veera Vala:
Quote from @Olivia Feller:
For insights about the STR market in Indy, I'd recommend reaching out to Tyler Lingle with Roots Realty in Indianapolis—Roots specializes in helping investors and Tyler would be a good realtor to have a resource as you consider if that location would be the right fit for you!
Side note—my sister and I run a one-stop-shop creative studio for STRs—including interior design, murals, branding, and direct booking websites to help hosts stand out. As things progress, feel free to reach out if those are things you're looking to hand off to someone else!
I would love to connect with you and your sister regarding designing. Thank you
@Veera Vala We're excited to connect!
- Member since 2021 · 167 posts · 141 votes8mo
Quote from @Fizza Ali:
I'm a professional with a full time job looking into buying my first STR. I've spend countless hours researching on AirDNA, reading posts, and watching videos to pick a market. It just feels like I missed the boat on getting started. All the popular markets seem either oversaturated, out of our budget, or the numbers just don't make sense. Looking to people with more experience on what are some markets today that would be a good place to start for a rookie investor or even a reliable resource where I can do my own research. I have looked into many markets but one that I narrowed down to based on our budget is northern Indianapolis. Ideally I'd like to invest somewhere like the Catskill Mountains or Joshua Tree (based on my connections to the area). But I'm open to investing anywhere where the numbers make sense! Thank you!!
Indy has been good to me, feel free to reach out with any questions.
- 8moCollin HaysBusiness MemberProperty Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
Try to avoid looking at the situation from a macro standpoint. We can get easily bogged down and distracted by looking at various macro factors. The economy, the stock market, etc. If you watch CNBC on Fridays, they will always utter phrases like "We will know have more direction next week after XYZ report come out." Yet when XYZ report comes out, there still is no direction, so now we are awaiting ABC report the NEXT week. Thus, "more direction" never comes.
You've got to ignore externals and find your deal. One of the best "deals" I ever made was in precisely the WORST time supposedly to buy property - 2021.My last thought is, find your market and then become intimately familiar with it. You aren't going to score a deal by scanning the country. You've got to know the market you are investing in. Only then will you have a chance to make a good deal. Be prepared to wait, and wait, and wait. Better to wait a year or two to score a good deal, than rush into a bad deal and spend the next 10 years trying to figure out how to get out of it.
- Property Manager · USA · Member since 2018 · 85 posts · 50 votes8mo
Hi Fizza,
I think you should spend less time researching markets because, like you said, that ship has already sailed. Instead, focus on finding a unique home—something with an exceptional amenity that's scarce in the neighborhood. Mountain views, an indoor pool, floor-to-ceiling windows, etc. That's what you should be looking for.
- Investor · Long Beach, CA · Member since 2025 · 6 posts · 1 vote8mo
Personally, I have seen the market in Joshua Tree growing for STR's over the years and is still actively doing well. I think that would be a good location to start with, especially considering you have connections in the area. For the numbers to make sense in Joshua Tree often requires a higher initial investment in amenities (think hot tubs, outdoor fire pits, and professional photography). If you're willing to go all-in on the desert lifestyle, the personal connection you have will give you a massive edge over a passive investor
- Investor · Member since 2024 · 11 posts · 4 votes8moThank you! Appreciate the input. The thought of going to a cold and far place like Indiana doesn’t sound fun 😅
Quote from @Deon Burks:
Personally, I have seen the market in Joshua Tree growing for STR's over the years and is still actively doing well. I think that would be a good location to start with, especially considering you have connections in the area. For the numbers to make sense in Joshua Tree often requires a higher initial investment in amenities (think hot tubs, outdoor fire pits, and professional photography). If you're willing to go all-in on the desert lifestyle, the personal connection you have will give you a massive edge over a passive investor
Join the conversationCreate a free account to reply, vote on answers and follow this thread.