Need advice on boat rentals/where to stay in Keys?

I have a buddy who is planning a family trip to the Keys and is considering either KW or possibly Hawks Cay. He’d like to rent a boat for their trip to do some cruising, fishing, island hopping, etc.
He runs a 24 ft SeaRay cuddy here and has a good deal of experience on the water.
I suggested about a 20 Ft CC that will allow them to get shallow but also go fish some reefs in a little deeper water.
Anyone else have suggestions or advice both on where they should consider staying, boat rental companies, and getting on some fish with the kids.
Thanks

2014 Key West 203DFS
1987 Landau

I would suggest islaromada. We have stayed at the Pines and Palms resort there several times . Ana and her crew always made our trip exclent it’s on the Atlantic side . As far as boat rentals check with Bud and Mary’s marina and over at Robbie’s marina . I hope this was some help.

Marathon is great…short term rentals in Key Colony Beach (in Marathon) Find a guide named Diego who operates out of Marathon. Boat rentals available right at Colony Beach Causeway. Have fun!

Hawks Cay is upper end and very nice. Key West Southernmost Hotel is nice. As for boat rentals, Robbie’s is very affordable but not the best boats/motors. There are a number of boat rentals in Marathon who will trailer the boat to your launch. If your buddy is fishing the keys for the first time, tell him to spend the money for a guide for a day. The money will shorten the learning curve…and there is a big learning curve to fishing the keys. Love the keys…can’t wait to get back there!

Bearcat

Thanks guys, great info. I’ll make sure he reads these posts.

2014 Key West 203DFS
1987 Landau