Santorini with toddler.
 

Were traveling to Santorini in late May, we have a one year old son, I'm wondering what would be best family hotel at a reasonable price. We want to stay in Oia. Also wondering if I need to book ahead. We sort of like the idea of finding a place when we arrive, my sister lives in Athens and said we might have good bargaining power if we wait until we get there, she felt we would have no problem since its still fairly quiet on the islands in late May-other feedback on this plan?? How many nights would people recommend on Santorini??

I think your sister is right, but with a child it is difficult to take that chance .
Have you looked at tripadvisor.com Santorini hotel reviews, I find ta very helpful.

A very good, reasonably-priced family hotel in Oia is the Anemomilos Hotel. They also have an excellent restaurant on the premises.

www.anemomilos.com

It probably won't be booked up in May, but if you know where you want to stay, why wouldn't you make reservations?

To see everything and enjoy the island you need to stay a minimum of 4 days.

I'd book in advance simply due to the toddler factor. It's not easy to get around Santorini with a buggy so you will want to stay somewhere that is not up tons of steps. Some accommodations are not child friendly either as many patios / balconies can face directly onto swimming pools or cliffs.

I know two couples who went to Santorini with a small child. The first did not enjoy it at all and said it was no place for a child (which I think was very much down to the place they chose to stay). The second, who read up in advance, thought it was one of the best holidays they ever had. So I would go for the pre-planned option to make sure you get somewhere that is easy to navigate with a toddler.

If you decide to leave it last minute I would still compile a list of places to try on your arrival.

Any suggestions for rental car companies on Santorini, given that we will have our son, it would be best if there is a rental company near the port. I would like to look at a couple hotel options that are well suited for a toddler, the Anemomilos Hotel does look very good, right now that looks like a good fit for us, any other options that people can recommend that we can compare to would help. What about Aris Caves??? The only reason we figured we would wait until we get there is to bargain a bit, but we have also not traveled overseas yet with our son, so we need to keep in mind that this could be an added stress and might be nice to know where were going ahead of time.

Aris Caves is in an excellent location, but you need to ask if an infant would be acceptable. Many hotels don't allow them. That's why I suggested Anemomilos, because I know they do. Also check Old Oia Houses, Lena's House, Thea Studios, Stelios Rooms and Aspa Villas.

Walking in and bargaining for a room isn't as commob as it once was. You'll be taking a chance on losing something you might really want.

"commob" = common