Advice needed for booking multiple rooms in Italy

You can look at booking.com and in the space for destination and dates, there is a box for how many guests and another box for how many rooms you will need. I make multiple reservations at one time for 3people, 2rooms. Then you can choose the type of room/bed arrangement.

For two families, you may want to consider apartment rentals for some of your nights, more room to spread out. Booking.com has those, too; filter by type of accommodation.

I have recently booked two double rooms for two couples for our 23 day multi-city stay in April/May 2017. I found emailing the hotels directly was the easiest and fastest. I researched my top couple choices, emailed them my dates and room choices and from most hotels got a quick response in English. I emailed them back with my credit card information and received a confirmation email quickly. Good luck!

There are literally thousands of rooms on Booking.com and other websites. You didn't say how much you wanted to spend. You also need figure out what part of town you want to stay in while in Rome.
It's a shame that you're just hitting the highlights as Rome is a 4 night minimum town, Florence is a 3 night town and Venice is a 3 night town. Remember that your first and last days in Italy will be wasted days--coming from the airport and getting to the ship port.
With so many people, it'd be nice to get a villa (with a cook) outside of Florence and do some day trips with a couple of rental cars.

Thank you for such quick responses! I love the Villa idea. Do you have one you recommend? How can I find something like that? Is that doable without a car?
I will look into the booking.com site. I had been surfing tripadvisor.

Thank you!

My family of 4 will have an extra 2 nights in Rome as we fly in advance of the others. Also planning a 3 day trip down to Sorrento with day trips to Capri and Pompeii

You should stay the first 4 nights (3 full days) in Rome. At most you could take a day trip (Orvieto?).
Florence and Venice for 2 nights each is kind of short (3 each would be better), but if that is all you have.
I don't suggest a rental car to stay in Rome, Florence, or Venice.

I presume the 3 days in Sorrento are after the cruise?

Hi Denise,
Check out airbnb for an apartment with multiple bedrooms, bathrooms, kitchen, livingroom, and washer/dryer. I did this for my adult family of four visit in early June 2017. Had an easy experience booking for Rome, Orvieto, Florence and Venice. Having some elbow room and private space was a must for my family travelling with 21 year old twins. Just plug in your parameters for each city, and choose from the map the areas your interested in staying. Good luck and happy travels. Also, read the reviews of your host and stay clear of bad reviews.

Ok hadn't considered Airnb, I'll look into that. I agree that apartments give more room and privacy. I'm struggling with this trip because usually when we go to Europe we do a house exchange and stay in one spot and take day trips. This trip has more family, more miles traveled and no car.

My rough idea is for my family to fly into Rome spend one night and go directly to Sorento for 3 nights. We return to Rome meet up with the rest of the family and see the Rome sights with them, stay 2 more nights in Rome which I know is short but the others have limited time abroad. I like the idea of 3 nights in Florence. For Venice we will have 1 night prior to our cruise and another night or maybe 2 after the cruise. Then we part ways and travel towards Genoa.

Thank you everyone for the suggestions. They've been more helpful in figuring out how to plan this trip.
Denise

I have had great success with VRBO and Home away for multiple nights in Europe. It's nice because you are typically working directly with the owners