Accommodations

Venice

Booking Engine:  AirBnB
Venue:  Vogue Apartment
Location:  San Polo district
Bedrooms:  2
Bathrooms:  2
Sleeps:  4
Room Rate:  $233
City Taxes:  4.00€ tax, per person, per night, in cash upon check in

Notes:  This is a nice apartment.  The host was great and met us at our taxi and walked us to the apartment.  He gave us tips on restaurants and how to get around the city.  There is a full kitchen and dining area.  Just note that the second bedroom has two single beds.  Great for a family with two kids!

Verona

Booking Engine:  AirBnB
Venue:  Armonie Apartment
Location:  Filippini neighborhood
Bedrooms:  2
Bathrooms:  2
Sleeps:  4
Room Rate:  $177
City Taxes:  1.50€ tax, per person, per night, in cash upon check in

Notes: This apartment has been renovated and was beautiful inside.  One bedroom has a private bathroom.  The second full bathroom is in the hallway.  The kitchen area is small, but functional.  There is not a separate dining room, just a small table in the kitchen area.  The hosts were wonderful.  She really went all out, leaving roses on the pillows and even giving my wife a birthday present.  We loved them!  They made us feel at home, gave us some great info about the area, recommended restaurants and even gave us tips about Italian culture.

Florence

Booking Engine:  Expedia
Venue:  B&B Magnifico Messere
Location: Florence's Duomo neighborhood
Bedrooms: 1
Bathrooms: 1
Sleeps: 2
Room Rate: $115.70
City Taxes:  3.00€ tax, per person, per night, in cash upon check in

Notes:  This is a small 3 unit bed and breakfast with a shared kitchen.  There was plenty of food and drink in the kitchen to eat for breakfast or to have a snack. There is a small eating area and TV in the kitchen area.  Each bedroom has a double bed with a small bathroom.  The location was great.  It was only a couple blocks from the Duomo.  The woman checking us in didn't speak any English.  We used Google translate to communicate.  She called the host on her cell phone and handed it to me so he could give me breakfast and check-out instructions in English.  He left me his number in case we needed him during our stay.  There was a foul smell in our room.  When I called and complained I was told it was the building and nothing they could do.  The units are not on the first floor.  There is a small lift.  We had to take a few trips with the lift to get all our luggage to the room.

La Spezia

Booking Engine: AirBnB
Venue: Margot House
Location: Center of La Spezia near train station
Bedrooms: 2
Bathrooms: 2
Sleeps: 6
Room Rate: $150
City Taxes:  2.50€ tax, per person, per night, in cash upon check in

Notes:  This apartment is just down the street from the train station.  It is a little bit of a walk from the train station.  Without luggage it isn't a bad walk.  Not so much with luggage in tow.  They left the keys in a locker on the way to the apartment.  Just note that the street addresses were not easy to figure out.  So we walked by the key pickup location.  I had to walk back to find that location myself.  We never saw the hosts at this apartment.  I was able to communicate with them via WhatsAp.  The apartment had two bedrooms with two bathrooms.  One attached to a bedroom and the second in the hallway.  It had nice size bedrooms.  The unit is not on the first floor.  There is a lift.  There is a cute balcony outside the kitchen with a nice view of the city.  They do have a small washing machine in the hallway.  We were able to do laundry and hang the clothes in the apartment to dry. (That was a site!)  The amenities in this unit were not the same as other locations.  The host advised us they were not allowed to have food products in the apartment.  They had an induction stove and coffee maker we couldn't figure out.  So we had to go out for all our food.

Chianti

Booking Engine: Verrazzano Castle website
Venue: Verrazzano Castle Farmhouse
Location: Greve in Chianti
Bedrooms: 1
Bathrooms: 1
Sleeps: 2
Room Rate:  80€
City Taxes:  1.50€ tax, per person, per night, in cash upon check in

Notes:  In order to book my reservation I had to call them on the phone and give them my credit card information.  To check-in we met the host at the wine shop.  Then drove about 1.5km up a small country road to the "farmhouse".  There are 11 rooms in the farmhouse.  It sits halfway up the hillside with a view down the valley and up the other side, to the castle on the other side of the valley.  Back over 1,000 years ago they were enemies with Castle Verrazzano as liege to Florence and the opposing castle liege to Siena.  Now they are rivals in the wine business.  The building is old, but nicely renovated.  There was a charm to this old building along with all the modern amenities.
Breakfast was included in the room fees.  The breakfast area is a classy room with a buffet style breakfast full authentic Italian breakfast cuisine.  This was by far our favorite breakfast of the trip and trust me my wife is all about breakfast!  As a guest in the farmhouse we were permitted to drive another 2km up a small dirt road to the Castle and walk around the grounds.  The place is beautiful!

San Gimignano

Booking Engine: AirBnB
Venue: Apartment in the medieval city
Location: Inside the walls of San Gimignano
Bedrooms: 2
Bathrooms: 2
Sleeps: 6
Room Rate: $99.86
City Taxes:  1.50€ tax, per person, per night, in cash upon check in

Notes:  The host for this apartment was great.  She met us outside the city walls.  She had me stay with the car while she walked everyone else to the apartment inside the walls.  She drove back out to meet me and take me to free parking outside the walls.  Then drove me and the luggage back to the apartment.  There is one set of stairs to the apartment.  The two bedrooms have attached bathrooms and there is a nice size kitchen in the unit.  The host gave us tips about the city and some insight about maintaining apartments inside these old cities.

Siena

Booking Engine: Hotel Website
Venue: Hotel Athena
Location: Just inside the Porta San Marco
Bedrooms: 1
Bathrooms: 1
Sleeps: 2
Room Rate: $181.50
City Taxes:  2.50€ tax, per person, per night, can pay by credit card

Notes:  This hotel is just inside the city walls with free parking.  When we checked in they gave us a map of the city and suggestions about sightseeing.  The rooms were great.  Our room had a beautiful view of the countryside.  From our room we could see the outdoor bar that had the same view.

I watched the sunset from the bar, while waiting for dinner.  Our dinner at the hotel restaurant was great and they had a good spread for the buffet breakfast.

Orvieto

Booking Engine: Hotel Website
Venue: Hotel Corso
Location: On Main street inside city walls
Bedrooms: 1
Bathrooms: 1
Sleeps: 2
Room Rate: $88.50
City Taxes:  2.30€ tax, per person, per night, in cash upon check in

Notes:  This hotel is inside the city walls, walking distance from the funicular.  With luggage this is a bit of a walk up a hill, but manageable.  The hotel was in a convenient location for walking through the city.  It is a basic 3 star hotel.  Breakfast was included in the room fees, but nothing compared to Verrazzano.  There was water on the floor in my parents room, so they got upgraded to a suite.  That was a nice room.  Ours was smaller.  It was fine, but did not compare to our hotel in Siena.

Rome

Booking Engine: AirBnB
Venue: "Domus Fabia" my home at the Colosseum
Location: Monti district down the street from the Colosseum
Bedrooms: 3
Bathrooms: 2.5
Sleeps: 8
Room Rate: $227
City Taxes:  3.50€ tax, per person, per night, in cash upon check in

Notes:  This apartment is just down the street from the Colosseum and Roman Forum.  It is not on the first floor, but there is a lift.  In the entry way there is a place to store your shoes and a basket of slippers for guests to use.  Even though it is on a main street, when the windows are closed you cannot hear the busy street.  The apartment was HUGE, by European standards.  It looked newly renovated, had classy decor and all the amenities you could want.  A fully equipped large kitchen; a living room; a master bedroom with an attached bathroom; another full bathroom; a half bathroom; a third bedroom with a single bed.  Bonus: they had a washer & full-size laundry rack.  If we were going to stay in Rome for a week we would stay here.

Accommodation Awards

My favorite:  Rome, Domus Fabia

My wife's favorite:  Rome, Domus Fabia

Biggest Disappointment: Orvieto, Hotel Corso

Best Location:  San Gimignano, Apartment in the medieval city

Best View:  Siena, Hotel Athena

Best Host:  Verona, Armonie Apartment

Largest rooms:  Rome, Domus Fabia

Best Breakfast:  Chianti, Castle Verrazzano Farmhouse

Best Dinner:  Rome, Domus Fabia

Final Words of Advice

• To search for accommodations I used Expedia, Bookings.com, AirBnB & Google Maps to find locations.  I didn't like the descriptions or ease of use for bookings.com. I found AirBnB the easiest to use.  I didn't want to stay at a hotel chain.  I wanted something a little more authentic for the areas we were visiting.
• Tuscany was a little more difficult to find the kind of venue I was looking for, so I read some of the travel blogs.  That is how I found the Castle Verrazzano Farmhouse.  
• Don't give up if one of the larger booking engines shows no rooms in a venue you like.  Go to the hotel's website and check availability there.  I was able to find rooms when booking direct even though the larger booking engines had no inventory.  
• Italy has a tourist city tax.  It varies by city.  It is not included in the rates when you book your rooms.  AirBnB and some smaller Bed & Breakfast venues require a cash payment for the city tax when you check-in.  Make sure you know how much this is before you get there.  This is most important for your first night's stay.  You need to get your euros before you check-in!
• Don't give out credit card information via email.  Castle Verrazzano communicated via email.  I chose to call and give my card information rather than risk emailing it.
• If you are booking separate rooms for another couple or your kids make sure they are in the same building.  Some of the apartments on bookings.com are listed with multiple units, but are not in the same building.  I booked two apartments and when I tried to get the street address from the host I found out we were not in the same building.  So I had to cancel and find another location.
• When I booked I always made sure that I could cancel without penalty.  Some will allow you to cancel up to 24 hours before your check-in date.  Others up to 7 days prior.  So make sure you keep track of the last day you can cancel without penalty.  It paid off when I had to cancel one venue because we changed our plans.
• Read the reviews.  Some of the pictures online are from years ago and the rooms don't look as nice when you get there.  So read the reviews.  I was able to save a lot of money, but if I just booked online without verifying through reviews I don't think we would have had as good an experience.
• AirBnB does not show the street address until the cancellation period is over and you make your payment.  Most hosts do a great job responding to questions if you message them through AirBnB.  They will give you restaurant tips and information about the local attractions. 
• Pay attention to bathrooms.  A lot of the locations show 2 bathrooms, but one is only a half bath or a full bathroom that has a tub and not a shower.  I didn't book a unit until I saw a picture of both bathrooms and confirmed they had showers in both or read a review stating the bathrooms would meet our needs.  If you are a big person just note that some of these showers are 3'x3'.  I am 6'3" and found some of those showers a bit cramped.
• A bad night of sleep can ruin your day, so make sure you are staying at the right place.  You don't have to spend a lot of money to get a nice place, but you do need to pay attention to the details when booking.  We averaged $109 a night for our trip and were only disappointed in one location.  Even that was fine.  It just didn't compare to the others.
• Give the venue a review.  It helps other travelers and helps the smaller hosts build a good reputation if they give you a great experience.  You can find my review on all the AirBnB locations that I mentioned.