We have stayed at Diamond Head Resort twice and loved it. Beach area is clean and was not crowded when we went in July last year. Also We have been to Treasure Island and liked it as well.
June would be low season .Warm with some scatered afternoon showers . I would recommend a condo .You would have more room to spread out as well as a kitchen . Plenty to do in Ft Myers focusing on water activities . Whether its fishing or renting a pontoon boat or exploring the beaches . Mind you we did have some issues with murky water at times due to army corp of engineers releasing water thru local river which feed into gulf . At that time year you should be able to negotiate a good rate on 2 br condo . probably well under 1000/week for oceanfront .
If the carrier is Allegiant (which I know flies out of Springfield), your destination airport will be Punta Gorda, about 50 or so miles away. We were in Ft Myers a couple of summers ago and even though it's supposed to be off-season, it was still busy. We stay on the southern end of Estero Island or over on Sanibel. But as for the distance from Punta Gorda, you should also consider Siesta Key, just south of Sarasota - may be a little closer to the airport than Ft Myers.
When we got married a few years ago the 1st week in June (great weather not too hot yet) at Fmb my whole extended family went with kids all ages. They were right in the previous post this is off season so rates on ocean front condos go down. We stayed at the Caper Beach Club with ocean front lanai and full kitchen. Very well maintained and Times Square/pier for shopping restaurants is walkable. This is my favorite beach I've been to including California, Texas and other Florida beaches
I agree with Michelle, we stayed at the Caper Beach Club as well and loved it. FMB has many condo entals to choose from.
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