Best way to book stays in Italy

I have had excellent experience booking through booking.com, in Italy and other European countries. They offer excellent descriptions of the rooms, including square footage, clear lists of facilities and services, and an internal means of communicating directly with the lodging with special requests, etc. Reviews shown are always from actual booking.com guests, and give a good picture of experiences.
Two special personal experiences:
1. Once in Spain, I happened to be at the reception counter of a small hotel, when the manager took a call from a person with a messed-up reservation, made through some booking site. I asked her if they have a lot of problems like that, and she said that they were enrolled with various booking services, and had a lot of problems with reservations, but never a problem with reservations from booking.com, she volunteered.
2. I had a 40-day trip to Italy scheduled for April and May of 2020, I spent a lot of time researching, planning and making reservations through booking.com, about 10 in all. I was excited about all my lodging choices and prices. Well, we all know how that travel season turned out! As dismayed as I was, I made one toll-free call to booking.com, and their customer service person went one-by-one, cancelling each reservation, including for one making a direct phone call to Italy to confirm the cancellation, while I was still on the line. E-mails confirming each cancellation came through even while I was still talking to her. Great service, at a horrible time! And I wasn’t spending a dime right then, just canceling arrangements.
I know some people encourage travelers to book directly with hotels and inns, but I have generally found better service, quicker and better communication, and equal, often better, prices with booking.com.

I don't think there is a right or wrong answer to this. It depends on your own personal style and the type of accommodation you are looking for. If you search on this forum you will see a lot of discussion, some a little heated, on whether to book directly with the property or thru a "middleman" like booking.com or VRBO. For me, whenever possible, I book directly with the property unless there is no way to do so. Whenever possible, I book smaller, local and family owned inns, and I like my money to get to them in full. I have often gotten perks by working directly with the property whether its a nicer room or included breakfast or similar. There are some cases that I have used a contact at the property to help me with my trip planning--like transportation or hours for museums, suggestions for wineries to visit, etc. In some cases, we've developed a relationship before we even get to the property, and I like that. I've also found it easier to work directly with the property for special requests. About a month before our trip to Sicily that had been completely planned, I injured my knee. I contacted the properties to ask about a room on a lower level or the possibility of an ice pack.

In all our travels in Europe, I've only had a reservation cancelled on me once, a hotel in Paris that I booked thru Booking.com. I ended up contacting the property directly to determine the issue, and I ended up booking with them directly.

I also had to cancel a trip due to COVID. It was a 4 week trip to France and Spain, and I had booked at least 10 properties. I sent an email to each property when I cancelled. It probably took me 3-5 minutes to send each email. Some of these places had helped me with my trip planning and I wanted to thank them for their help and explain why I cancelled. I've now rebooked with most of them for the trip we are doing in a couple months.

We were in Sicily in April and May. I booked two different agritourismos. Both I found in the Rick Steves guide and both turned out to be amazing. I would return to them in a heartbeat. If I can't get good recommendations from the RS guide I search other sources including putting a post here on the forum looking for specific recommendations.

Typically when we travel, we stay in at least 8 places. Where I stay is important to me and I do some research to make sure its a good fit.

I just finished planning a trip to Washington State. We needed a hotel for 3 nights in Seattle and it needed to be close to my son's house where there are few hotels. A few were super cheap which my son strongly discouraged and the other two were quite high priced. (What the heck, Seattle? I can stay cheaper in Rome, Paris, and Vienna, basically anywhere in Europe!) I tried to find something reasonable on booking.com and then went to the hotel specific websites (Best Western and Marriott) I was able to get a lower price booking directly with Best Western, further, if I would have used booking.com, I would not have earned any points on the stay.

I use Kayak.com, booking.com and tripadvisor.com to check on lodging. I like the map feature that tripadvisor and booking have.

I generally stay in apartments hosted on AirBnb. I research the spots and make sure they have several good reviews. I have been very pleased because generally I get more space and amenities for the same price as a hotel. Also, I am generally staying in a neighborhood where I get a more local experience. The downside can be that it might be harder to get to public transportation, but I research that too.

It is a mix.

Many use AirBnB or VRBO, I try to stay away from them. They might be good for longer stays, but for a shorter stay it seems like work and the main comment I hear is "what can I do with my bag until I can get in my AirBNB?" some 6 hours after arrival.

If preplanning well ahead, I will try to work directly with a place, found either in a guidebook, google search using Maps, blogs, or Booking.com

Since we book many nights a few days ahead, but also for some planned well ahead, we use Booking.com. It is easy, safe, and you have a good selection of types of properties, from hostels, BnBs, Hotels (Big and small), to apartments and whole houses. Not mentioned often, but if you use them multiple times, you do "earn" status, getting discounts and deals beyond the rack price.

We use Booking,com both because of the verified reviews and the maps with search filters. However, the cancellation and refund policies are still determined by the individual landlords, so you must be very careful to review each before reserving.

I can see using AirBnB and VRBO when a kitchen or more space is desired. But, I never seem to find anything that meets my criteria for price. By the time cleaning, taxes and fees are added the place is quite a bit more than the other accommodations I'm looking at. Maybe it works better for longer stays, larger groups and for people that budget for upper middle and higher priced accommodations. I've also noticed that cancellation policies are often far more severe.

I did use VRBO for a week stay in Kauai. That or AirBnB pretty much dominated apartment type rentals.

Like the others, I agree -- it's a mix. If you're going to be in a place more than a couple of nights, then I definitely prefer VRBO or an Airbnb. To me, the option of being able to eat in at least for breakfast, and sometimes for other meals if restaurants get boring, or we're just tired, is a bonus. I also like the extra room of almost all of them as compared to one room that his a hotel room. I've stayed in a few for only a night or two. You can see a lot of photos for most of them. Even for a short stay, I find them generally ok, but it is likely to be more of a hassle picking up the key, etc. Nearly all have been able to let me drop bags before actual check-in. One host who worked full time had a deal set up with the coffee shop next door. They held our luggage, securely, for a few hours without a problem. On both sites, you'll find many accommodations that are less expensive than a hotel. Some Airbnb's list on booking.com as well. If you see one you like, always check Airbnb and VRBO as well. Prices differ. In dozens of bookings, I've never had a problem with either Airbnb or VRBO.

Whomever said you can develop relationships with the owner/manager of both Airbnbs and hotels before getting there, I'd agree. If you speak the language, you'll get even better service. But, that said, I've never met a host who doesn't speak at least some English.

When we're looking for a hotel, I generally use booking.com . I've heard too many horror stories about kayak, expedia, etc for it to be worth the risk. You pay a bit more in you book refundable, but that's ok to me. With many of the properties you can cancel up to a week, or even a few days, without penalty. But, read carefully before you commit. The cheapest rates are generally nonrefundable. Booking's customer service is excellent.

Sometimes I book through the hotel directly. Sometimes it's a better deal; sometimes not. It also depends on how much time you want to spend shopping around. Checking booking, then contacting every hotel, is time consuming. With agritourismi, you will generally do better contacting directly; some you can only book directly with them. However, www.agriturismo.it lists a lot of properties and is very useful is weeding through them all and booking.

If you'll have a car, pay close attention. Many VRBOs and Airbnb's do not have parking, whereas, of course, hotels do.

Booking.com has plenty of apartment/home rentals as well as hotels, so I keep it simple and most often use them for all of my accommodations. I have used VRBO and AirBnB, and I've never had a problem, but I think the risk is higher with them.

This is not meant as a slam against third party booking sites or those who use them. Just a recitation of our experiences.

We always book directly with the hotel or B & B. Using email and telephone calls (not really that expensive considering the overall cost of the trip) allows us to deal with them personally. We don't even use their own booking site, and have never had a hotel or B & B not let us make reservations. Doing things that way allows us to clarify any areas of possible misunderstanding, and we've never had a problem of any type. If a problem were to arise, we would be dealing with them and not a third party site. Just somthing to think about.

My rule of thumb is anything less than 3 nights is a hotel and anything over is an apartment. So Arriving Monday and Departing Friday would be an Apartment. I have used both Airbnb and VRBO. You would do the same research for Hotel or Apartment, read reviews to see if there are any red flags ( for me it would be: Location, No elevator, loud construction, far walk to public transport, no nearby grocery store, plumbing/water issues) and price point and availability. Even for Booking.com you are going to want to perform research on the property. If I do go with a Hotel it must have breakfast available, that is just one of my requirements, so we don't waste time wondering around looking for a protein based breakfast. In the apartment I have the luxury of making us a quick breakfast early, packing snacks and we are out the door, plus it is just so much fun to go to the local grocery store and in Italy that means lots of tomatoes!
In all our travels every AirBnb has been wonderful with wonderful and helpful hosts. I never feel like I am alone in any city, in Florence our host even offered to drive us to the airport for an early morning flight if the Taxi they booked for us did not arrive (which I guess can happen sometimes).

hey hey steve
what places are you planning on staying and will you have a car or travel by train? if by train i would stay near train station, take a taxi to hotel/apartment, use at a taxi stand not flagging them down, not pulling luggage up or down cobblestone streets
if using a car, make sure there is parking and cost, not traveling in city center with ZTL zones.
always read fine print and reviews, what filters you need/want (mobility issues lift/elevator, what floor (first floor is really second floor), how many stairs/steps to climb with luggage, arrival times 2-4pm and departure times 10-11am unless early approval or rent day before and inform owners/host you arrive next morning. seen and heard too many "ugly" stories about hours having to wait with their bags.
cross-pollinate.com
pick your city and see what's available and where you want to be. the owners of this are a couple that started the beehive in rome
tuscanyaccommodation.com/ tuscany-apartments
apartmentslucca.com
pick between inside or outside walls. many small villages and towns around.
cucina-italiana.com
cooking school offering half day classes plus accomodations to check out
tripsavvy.com/ lucca day trips
many small towns to cruise around thru that not many tourists adventure to. they all want to see the same places with crowds, long lines. see someplace different, few villages/towns have thermal springs to relax at.
visit the barga and garfagnana areas and drive along the serchio river and see the "devils bridge"
a train ride to pisa and also to cinque terre
tripsavvy.com/ lombardy and italian lakes cities
booking.com
look for the area you want to explore and check apartments available. used them few times in geneva, venice, florence, paris, rome.
vrbo and airbnb are sites to use but they do charge large fees for many things, like cleaning, resort, parking, service, etc. i stay away from them
tripadvisor.com/ vacation rentals
i've used them for couple in paris and london
some places are no longer on sites since the pandemic started for couple years, many prices have gone over the moon with owners wanting to make up for all the loses they have endured.
hope you find some answers to your questions and places to look at and find a place you're comfortable in. good luck
aloha

Hi Steve,
There is also a newish player in the game called 'Plum Guide'. We just used them for London and rented a fun property from their listings. The irony was that Plum's HQ itself was a mere 5 blocks away--who knew?
We were in the Cotswolds just prior to London and used VRBO for the 5th time. Some of our past VRBO landlords and landladies have rolled their eyes at its mention. Apparently they'd had some hassles dealing with that outfit.

It takes all of my diplomacy and gnashed teeth now to refrain from bashing the knuckleheads at Booking.com. So I'll try to stick to facts.
Four years ago, they called us a mere two days before departure to inform us that our cherished splurge rental in Uzes, France had fallen through. Given that we'd paid in full many months earlier, this came as a shock. *What made matters infinitely worse was that we were just then dealing with a particularly messy family tragedy (we'd nearly cancelled due to it) and the last thing that we needed was foolishness on the scale that Booking.com was inflicting on us then. I pleaded with management at Booking.com to clarify what the hell had happened and was utterly stonewalled again and again. No meaningful explanation was ever given.

We soon resolved all the nonsense by contacting the Uzes owners directly. They were professionals and assured us that our reservation had never been at risk. We received no apology from Booking.com and never used them again.
*Steve, if you might want contact info for a great rental in Bevagna, Umbria, we would be happy to connect you with the associated real estate agent lady.
Good luck!
I am done. The end.

We were in Europe for 3 weeks in May and June. We booked 2 hotels (London and Amsterdam) and 1 apartment in Venice, via booking.com. Everything went well and we were very happy with our accommodations and service, we even had to change our reservations for London and that went smoothly. We would stay in all 3 places again. Our accommodations in Milan, Pasteum and Florence were via the Rick Steves guide book and we booked directly with the owners. All of them were wonderful and we would stay there again. Conversely, friends of ours with a family of 5 are currently in Spain. Most of their reservations are via Airbnb/VRBO. Everything went well, EXCEPT one location was nothing like the pictures and was unacceptable. They had to make other accommodations. I don’t have details yet (they are still in Spain) as to refunds etc.

I’m in Italy now staying in my 2nd of 8 accommodations for my month long trip. I booked all of them thru booking.com. They range in duration from 3 days to 7 days. I’ve been using booking.com exclusively for 10 years and have never had a single problem. Most accommodations offer free cancellation and no prepayment, but you do want to make sure before you book. Most also have very generous timeframes to cancel free of charge. This site makes arranging long trips with numerous destinations so much easier; I love booking.com!

It looks like you will stay in apartments all the time and then this is not relevant.

I use booking.com for my reservations, but on our recent trip to Scotland booking.com "failed" us. The thing is Booking.com distinguish between private and shared bathroom. We checked the photos and could see that the bathroom was en-suite, but the hotel had shared, private (non-ensuite) and private (en-suite) bathrooms. Because booking.com doesn't know about en-suite, they booked a private bathroom for us and - you guessed it - we ended up with a non en-suite.

It's the first time in more than 20 years of using booking.com this has happened, but it was not pleasant. I don't know what the solution is, except use booking.com for search and then book directly with the hotel.

I use booking.com for my reservations, but on our recent trip to Scotland booking.com "failed" us. The thing is Booking.com distinguish between private and shared bathroom. We checked the photos and could see that the bathroom was en-suite, but the hotel had shared, private (non-ensuite) and private (en-suite) bathrooms. Because booking.com doesn't know about en-suite, they booked a private bathroom for us and - you guessed it - we ended up with a non en-suite.

I have seen listings on booking.com where a room is listed with "private external bathroom". The fault is more likely that of the property owner who owns the listing rather than the platform itself

Not Italy but England.
Right on cue, VRBO just emailed us with the update that our Cotswolds host has rated us poorly. That came as some surprise as we have never before received anything other than mostly-positive 5 stars on any rental platform across the globe. Hosts have been pleased enough to give rave reviews, personally provide transfers and in one case, even offered a few extra days without charge. Our London host from that same English trip just sent us a warm 'farewell' message and invited us back, for example.

Apparently, that Cotswold host gave us the lowest one-star grade for 'house rules and also cleanliness'. Hmmm... Not sure what the 'house rules' bit was about. We made an honest effort to abide by them all. As for cleanliness, we have always placed a premium on trying to respect properties and 'unclean' just does not fit us at all.
We'll cop to being a bit needy. One toilet kept malfunctioning despite my repeated repair efforts. And a rear door would not close properly, apparently not the first time that this had happened. With a mind towards protecting their cottage's security, we asked the host and her husband to drop by and remedy that issue. And as for our role as renters there, mea culpa: we are still not fully conversant on how to use smart phones, having just bought our first-ever. The resultant communication awkwardness was mostly our fault.

My wife rightly just remarked, "Surely, they've got us mixed up with other renters"--that host owns 4 other rental properties.
*Note that we are currently dealing with a family tragedy and that Cotswolds host had an inkling about that. It feels unseemly to dump such a low rating onto earnest travelers who've just filled your pockets (we stayed more than 2 weeks).
I am done. The end.

When booking hotels, I book directly with the hotel instead of using a 3rd-party service. Especially if the hotel is a family run operation, as many small European hotels can be. I would rather have the relationship with them rather than have someone in between. I have used VRBO once, I typically use AirBnB and only rent with SuperHosts. My current trip is 100% AirBnB in 6 different locations over 31 days. I have never had any issues in Europe when using AirBnB's.

I don't know if this counts but we've had two interesting experiences with U.S. hotels either booking directly with them or attempting to do that. One of them we'd booked to attend a wedding closed completely and didn't tell me; I read it online somewhere after I was unable to reach anyone for a question. In the other case, I'd sourced some rates on the web - including via the hotel's own online reservation service - but the over-the-phone price they offered was quite a bit higher. ??? The desk person said that using the online booking service usually provided a better rate. LOL, so much for the "relationship" factor, eh? Oh well.

I have booked a fair number of hotels in Europe on booking.com and haven't had any issues so far. They helpfully tracked down the owner of a B&B I'd booked who wasn't responding to multiple requests for information so that was nice.

Gregg, very sorry to hear that you're dealing with yet another family tragedy. Two in four years... :O(

Thank you for that Kathy, appreciate it. God's sense of humour to have family tragedies occur right before and now, right after, one's travels. Both were mind-blowers, well outside the normal parameters of regular expectation.
That's not cricket old boy
I am done. The end.