Venice Neighborhoods, Where to stay?

I don't know about apartments, but we found that the area near the main train station in Venice is the most affordable. There are several B&Bs in that area. From there, it is easy to walk anywhere in the city.

We have stayed in San Marco, San Polo, and Dorsoduro. By far our favorite is San Polo as it is convenient yet more residential-feeling (fewer big hotels) than San Marco. Dorsoduro is lovely, but it is not as easy convenient in terms of getting to other parts of Venice, IMHO.

That said, this is late for making reservations for May, so if you find a place you like, go for it. Venice is really very small so the exact neighborhood is less important than a place you like. The far eastern end (St. Elena) is very residential but a bit removed from the major sights and restaurants so maybe not the best choice, unless you are having quite a long stay. Do avoid the Giudecca as coming-and+going from there always requires a vaporetto and takes extra time.

How many nights do you have in Venice?

I always stay in Cannaregio. It's full of great restaurants but is still very quiet, even in the middle of the day when all the day trippers are in town. It also feels more spacious, with more broad promenades along the canals than in other neighbourhoods.

For me, the highlight of every Venice trip is just strolling around its neighbourhoods and enjoying the city - and Cannaregio is a perfect base from which to do so.

The last time I was in Venice, I spent 5 nights in a 1 bedroom apartment in the Cannaregio area. It has a beautiful view and the owner lives in the same building.

She also has a 2 bedroom that might work for you and your bestie. Here's the link to it.

The listing includes pictures of the apartment, the neighborhood and the views. My 1 bedroom was lovely, but not as impressive as the 2 bedroom, although you might have to toss a coin to decide who gets the fancy bedroom.

There's a Coop grocery nearby. There's only 1 flight of stairs to the apartment which is on the European 1st floor.

Another vote for Canareggio.
Easy in and out for the train station and the airport (less bridges to take luggage over), lots of restaurants and supermarkets, and easy access to vaporetti going every which way.
It's also pretty quiet if you get a bit north of the Strada Nuova.
An apartment is my preferred place to sleep too, but be quick to get one you like!

We stayed here in 2015, and it was great with two bedrooms.
Traditional architecture, and very clean and quiet.
Really nice host; and big rooms, and a tremendous balcony out back.
I would stay there again!
https://www.homeaway.com/vacation-rental/p840077
I see there is still a bit of availability in May depending on your dates.

Dorsoduro is great. We mighty try this apartment next time:

http://www.thevenetianterrace.com

We were there during Easter 2018. After much research we decided to stay in the Dorsoduro area at Ca Centopietre. It was a wonderful stay, it’s easy to get around. We walked most of the time to experience all that Venice has to offer. Great to walk early morning when no one is out on the streets. I walked by myself to St Marks square to experience the sunrise then attended Easter mass, lovely experience. You’ll get lost as everyone says about Venice but you’ll find your way around. I will definitely stay there again. Enjoy your trip,,

On an RS Venice trip we stayed at this hotel.
https://www.hotelserenissima.it/

You can click to translate the page to English. It is only about a 4 minute walk to St. Mark's Square and we found most of Venice very walkable or short water taxi hop.
Small hotel and for Venice, I think the prices are good.

Wow! So many suggestions, thank you all. We haven't booked yet, and are still comparing this flat to that one and it's amenities. We'd like a balcony for a view if possible. Any restaurant recommendations? Cooking classes or specific tours anyone can recommend?

I highly recommend the Venice Bites Food Tours:
https://www.venicebitesfoodtours.com/

The tours are run by two very enthusiastic American expats and are a great way to explore Venice, its history, and its best places to eat. Even if you don't do the tour, they have some great restaurant recommendations on their website split by neighbourhood:
https://www.venicebitesfoodtours.com/our-favorites-in-venice/

My own favourites for where to eat are:
Alla Vedova in Cannaregio
La Palanca on Guidecca
Cantine del Vino gia Schiavi in Dorsoduro

We love Canareggio, very residential and quiet at night, but everything is easily walkable.

As someone mentioned above, Venice is small enough that one can walk anywhere. For a visit of only a few days, we would not opt for an apartment -- but that's just us as we'd rather eat out. We've stayed at Pensione Guerrato in the Rialto Market area a number of times and have always been pleased. They also have an apartment to let. We've not used the apt., but wouldn't hesitate based on our stays at the hotel.

How is the local wine in Venice? When we visited Cortona in Tuscany last summer we found the local/house wine to be lovely and decided no need to get upsold on higher priced wines on menu's. Any vineyards in the area you could recommend? Does anyone take the gondola rides or is that too touristy/cheesy? We travel to Lucca after Venice and are looking forward to that as well. Thank you for keeping the suggestions coming!

The last time in Venice I stayed at a two bedroom apartment next to the Frari Cathedral; it was everything I had ever dreamed about. The area is residential and very quiet with little eateries and markets within walking distance. I especially loved watching the world go by from the second (first in Italy) floor. I am going back this June to stay there alone for 10 days because I felt so safe and loved it so much. I cannot recommend Casa Elena (Airbnb) highly enough; the owner was a dream to work with and even sent her son to meet us and walk us to the apartment.

The gondola ride is a very nice thing to do. Sure, tourists do it, and we eschewed it for several trips but then we visited Venice with a family whose 13 year old insisted we take the gondola tour. We loved seeing Venice from the canals!

I agree - Cannaregio. We stayed in a lovely little flat just 5 minutes from one of the vapparetto stops - Guglie - and it was a great launch pad for everything. When we were done, we walked 10 minutes to the train station and we were outbound. Heading to Italy / Venice and the Cannaregio again in August this year. As has been said - quiet, good food, etc.

As far as restaurants, I had a note in my file from last time - stay away from places with 3 languages on the menu! If you see an out of the way little place, with an italian menu, do your best to figure it out, ask questions, make an effort in your Italian and they will love you for it. We stumbled on so many awesome little holes in the wall, where the appetizers were out of this world. Stay out of the main square areas for the lowest prices. You'll pay 25% more if you are in a popular 'hang out' spot.