Looking for local advice or experienced STR investor insight Naples (south of Estero)

Looking for local advice or experienced STR investor insight Naples (south of Estero)

Investor · Northbrook, IL · Member since 2024 · 7 posts · 4 votes

I’m exploring STR-friendly communities in and around Naples (south of Estero) for a property my family can use part-time and rent on Airbnb/VRBO to help cover costs.

I know about Briarwood allowing sub-30-day rentals, but I’d love to connect with anyone who has insight, suggestions, or firsthand experience with other HOAs or communities that are truly STR-friendly in this area.

If you’ve invested or hosted in Naples or nearby, I’d really appreciate your perspective — feel free to comment here or connect with me directly.

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Interior Decorator · Nationwide · Member since 2017 · 44 posts · 35 votes
10mo

For upscale properties with 3 bedrooms and 2 bathrooms, we are observing: 

- An average occupancy of 65%, with seasonal peaks between January and April 

- Average annualized daily rates of about $450 per night, similar to last year 

- Consequently, the top performers are generating around $110K in gross annual revenue 

- Average listing price of for-sale properties: $800K 

- Rough Rent-to-Price Ratio (RTP): 14%, which is good but not great. I typically look for 15% or higher as a benchmark.

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  • Interior Decorator · Nationwide · Member since 2017 · 44 posts · 35 votes
    10mo

    For upscale properties with 3 bedrooms and 2 bathrooms, we are observing: 

    - An average occupancy of 65%, with seasonal peaks between January and April 

    - Average annualized daily rates of about $450 per night, similar to last year 

    - Consequently, the top performers are generating around $110K in gross annual revenue 

    - Average listing price of for-sale properties: $800K 

    - Rough Rent-to-Price Ratio (RTP): 14%, which is good but not great. I typically look for 15% or higher as a benchmark.

    • Investor · Northbrook, IL · Member since 2024 · 7 posts · 4 votes
      10mo
      Quote from @Justin Miller:

      For upscale properties with 3 bedrooms and 2 bathrooms, we are observing: 

      - An average occupancy of 65%, with seasonal peaks between January and April 

      - Average annualized daily rates of about $450 per night, similar to last year 

      - Consequently, the top performers are generating around $110K in gross annual revenue 

      - Average listing price of for-sale properties: $800K 

      - Rough Rent-to-Price Ratio (RTP): 14%, which is good but not great. I typically look for 15% or higher as a benchmark.



      Thanks, Justin — that’s really valuable insight, especially with the occupancy and RTP numbers you shared.


      Since you're an STR interior designer, I'd love your take on what design features or upgrades tend to deliver the best ROI. For example, have you seen things like game rooms, fire pits, or home theater setups make a noticeable difference in bookings or nightly rates for higher-end 3 bed / 2 bath properties?


      Really appreciate you sharing your expertise here.



    • Interior Decorator · Nationwide · Member since 2017 · 44 posts · 35 votes
      10mo
      Quote from @Danny Gallagher:
      Quote from @Justin Miller:

      For upscale properties with 3 bedrooms and 2 bathrooms, we are observing: 

      - An average occupancy of 65%, with seasonal peaks between January and April 

      - Average annualized daily rates of about $450 per night, similar to last year 

      - Consequently, the top performers are generating around $110K in gross annual revenue 

      - Average listing price of for-sale properties: $800K 

      - Rough Rent-to-Price Ratio (RTP): 14%, which is good but not great. I typically look for 15% or higher as a benchmark.



      Thanks, Justin — that’s really valuable insight, especially with the occupancy and RTP numbers you shared.


      Since you're an STR interior designer, I'd love your take on what design features or upgrades tend to deliver the best ROI. For example, have you seen things like game rooms, fire pits, or home theater setups make a noticeable difference in bookings or nightly rates for higher-end 3 bed / 2 bath properties?


      Really appreciate you sharing your expertise here.



      Absolutely yes. The goal is to be in the top 10% of performers in your market to command premium nightly rates and increase occupancy. We advise clients on this exact "game" every day.

      For example, we conduct an amenity study of 5 comparable homes next to you that you would compete with to see exactly what amenities they offer. Then we create a "Most Impactful" list that we recommend to meet and even exceed those standards.

      Philosophy:


      Strategic amenity selection is crucial for driving revenue and guest satisfaction. Focus on these key categories to maximize your property's appeal and ROI, ensuring every investment contributes to a top-performing listing.
      Outdoor Living

      Must have potential for high-impact features like fire pits, hot tubs, dining areas, or outdoor games to significantly boost appeal.

      Views & Proximity

      Properties with desirable views or close proximity to water, nature, or main attractions offer an enhanced guest experience.

      Premium Interior Features

      Potential for dedicated game rooms, high-speed Wi-Fi, or comfortable dedicated workspaces to cater to diverse guest needs.

      Easy Parking

      Adequate and convenient parking for the expected guest group size is critical for convenience and securing 5-star reviews.

      Garage to Game Room Conversion

      If driveway parking is plentiful, converting a garage into a functional game room or extra living space offers amazing added value.

      Noise & Light Abatement

      Ensuring quiet enjoyment of the property through noise reduction measures enhances guest comfort and prevents issues with neighbors.



  • Member since 2022 · 527 posts · 413 votes
    10mo

    Hi. I live in Marco Island and have 3 rentals here, too. We don't have any STR regulations here for the most part (much to the chagrin of us residents). I know Collier County (which Marco opted out of) has some registration requirements and parts of Naples have some requirements but otherwise, not too familiar. Sorry can't help more on Naples but I've had success in Marco (mine are condos which while we have HOA fees, I believe do better than most homes).

    • Investor · Northbrook, IL · Member since 2024 · 7 posts · 4 votes
      10mo
      Quote from @Patricia Andriolo-Bull:

      Hi. I live in Marco Island and have 3 rentals here, too. We don't have any STR regulations here for the most part (much to the chagrin of us residents). I know Collier County (which Marco opted out of) has some registration requirements and parts of Naples have some requirements but otherwise, not too familiar. Sorry can't help more on Naples but I've had success in Marco (mine are condos which while we have HOA fees, I believe do better than most homes).


  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    10mo

    I manage(d) a very house in Naples and it has struggled ever since Ian in 2022.  I am wary of the area when compared to comparable markets/submarkets a but more north like Sarasota, Bradenton, and Tampa areas.  

  • Benjamin AakerPro Member
    Rental Property Investor · Brandon, SD · Member since 2015 · 1k+ posts · 1k+ votes
    10mo

    Danny, you need to look at the deal as either an STR or a vacation home that you will rent out from time to time. As an STR, do your diligence for the area and don't kill profit by vacationing there. If you will be using it for yourself/family to vacation, you will struggle to make money. It'll be a vacation home and you will constantly be underwater. That's not a bad thing (everyone who just buys a second home is technically 'under water' from an investment lens) but you have to decide which way you'll go into it before buying.

    • Investor · Northbrook, IL · Member since 2024 · 7 posts · 4 votes
      10mo
      Quote from @Benjamin Aaker:

      Danny, you need to look at the deal as either an STR or a vacation home that you will rent out from time to time. As an STR, do your diligence for the area and don't kill profit by vacationing there. If you will be using it for yourself/family to vacation, you will struggle to make money. It'll be a vacation home and you will constantly be underwater. That's not a bad thing (everyone who just buys a second home is technically 'under water' from an investment lens) but you have to decide which way you'll go into it before buying.



      Thanks, Benjamin — that's really good advice. I'm looking at this as an STR first, and if I can use it on a few weekends when it's not booked, that's just a bonus.

      Ideally, I’d like to invest in larger multifamily, but STRs are the only way I can create losses right now as part of my tax strategy.

      It looks like you have a lot of experience, so any extra advice would be much appreciated.





      Thanks, Benjamin — that's really good advice. I'm looking at this as an STR first, and if I can use it on a few weekends when it's not booked, that's just a bonus.


      Ideally, I’d love to invest in larger multifamily, but STRs are the only way I can create losses right now as part of my tax strategy.


      It looks like you have a lot of experience, so any extra advice would be much appreciated.





      Thanks, Benjamin — that's really good advice. I'm looking at this as an STR first, and if I can use it on a few weekends when it's not booked, that's just a bonus.


      Ideally, I’d love to invest in larger multifamily, but STRs are the only way I can create losses right now as part of my tax strategy.


      It looks like you have a lot of experience, so any extra advice would be much appreciated.


  • Investor · Northbrook, IL · Member since 2024 · 7 posts · 4 votes
    10mo

    Thanks so much, Patricia — I really appreciate you taking the time to share that.

    That's super helpful to know about Marco Island being more flexible on STR regulations. If you don't mind me asking, would you be open to sharing the names of the condo communities where your rentals are located (or any other insights you've picked up along the way)?

    I’d love to learn more from someone who’s already had success in that market.

    Thanks again!

    • Member since 2022 · 527 posts · 413 votes
      10mo
      Quote from @Danny Gallagher:

      Thanks so much, Patricia — I really appreciate you taking the time to share that.

      That's super helpful to know about Marco Island being more flexible on STR regulations. If you don't mind me asking, would you be open to sharing the names of the condo communities where your rentals are located (or any other insights you've picked up along the way)?

      I’d love to learn more from someone who’s already had success in that market.

      Thanks again!


      All of my properties are in South Seas. Prices are still a bit high but have been coming down. HOA fees are high but believe it or not, we just gave owners a credit back for the last 3 quarters. We've revamped a lot and got insurance way down so we are good from that perspective as is much of Marco at this point (we were mostly impacted by Irma in 2017 and then again by Ian but nothing near what Irma did). There are a few other condo communities that allow weekly rentals or less (Riverside club, Seawinds, Apollo). There may be others. I got my 18th floor front corner unit in November 2024 and am already on track to gross over $100k this year (net ~$60K but I have a very small low interest mortgage) - my other two non corner condos gross between $80 - $90K/ year. I'll be honest, I put in a lot of work and don't use the properties myself and do much better than my peers according to Airdna and Pricelabs both in terms of occupancy and ADR so wouldn't count on these numbers.

  • Member since 2026 · 15 posts · 7 votes
    1mo

    Reviving this because I'm working the same problem from the other side of the map: a second home in the Estero/Bonita band that my family uses part of the year, with a seasonal rental to offset carrying cost rather than to produce a return.

    The framing earlier in the thread — decide whether it's a rental you occasionally use or a second home you occasionally rent, before you buy — is the most useful thing I've read on this, and I'd add one consequence. If you go in as a second home, the HOA question stops being "are short-term rentals allowed" and becomes three separate questions: the minimum lease term, how many separate tenancies per year are permitted, and whether there's a waiting period after closing before you can rent at all. That last one catches people, because it isn't in the listing and often isn't in the summary the HOA hands you.

    Two things I'd like to hear from anyone holding in Collier or Lee: what your hurricane deductible looks like as a percentage of Coverage A and how much you keep reserved against it, and whether a landlord policy or a homeowner policy with a rental endorsement priced better once you're occupying the place roughly half the year.

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