I assume you are landing at PIE. Frankly, with that late of an arrival, I would probably suggest stay the night near the airport, and then you can just jump on I295 from there and head down to Siesta Key. Plenty of hotels near PIE at all different price points.
Is there places to grab a quick bite to eat? Any specific hotel better than the other?
As you exit PIE, turn left on Roosevelt and follow it to the lights (Ullmerton). Turn left (east) on Ullmerton. Hotels in the immediate vicinity are: Quality Inn, Sleep Inn, Hampton, Comfort inn, Holiday Inn, Springhill Suites, Super 8, Courtyard Marriott. My personal preference would be the Courtyard, but you might find the Sleep Inn or Super 8 a bit cheaper.
Not sure which restaurants will be open at that hour. There is a Cracker Barrel, but they might close early. The Courtside Grill may or may not still be open, as it is a sports bar. You might end up at B. King, Wendy's , or McD, or grabbing a pizza to go at Papa Johns. In any event, you won't starve.
You can just hop on nearby I275 in the morning. Travel time to Siesta Key will be just over an hour, and there is only one toll on the Skyway. They take cash.Edited: 12 June 2018, 15:29
http://www.aviatorstavern.com/index.php located inside the holiday inn on Ulmerton is open till 11 pm
http://courtsidegrille.com/location/ off Ulmerton, serves till midnight on Fridays.
Holiday Inn rates via trip advisor $99
Spring Hill suites $108
All of the hotels in previous post are a few minutes from the airport and easy access to I-275 S for the next morning.
If we have navigation to guide us, is it difficult navigating at night time? After thinking it through, I wouldn't mind driving and staying somewhere by Sarasota. We are wanting to do the farmers market Saturday morning.
We have a short flight. 3 hours at the most. I think we will give it a try :)