A few questions . . .

Question

Flying in to Miami in mid-June, family of 4 (two teens). Thinking we’ll do two nights in Miami, two nights mid-Keys (Marathon or ???), two nights Key West, and then one more night before we fly home (haven’t decided yet; may just be whatever is close to airport).

Will probably do Margaritaville or Marriott for our two nights in Key West. But I want to book a nice oceanfront resort for our two nights mid-Keys. Something the kids can spend time at the beach; more of a tropical vibe. Want to spend no more than around $400/night. What would you recommend?

I know I’ll get sone maybe saying we need more time in one place or another, but we aren’t trying to do it all; just enjoy a nice trip exploring a new place. Thanks for any advice!

Answer

Your plan for the Florida Keys sounds reasonable for a relaxed family trip with teens, especially since you’re prioritizing quality time over packing in every activity. Mid-June is warm and tropical, so finding a resort with good beach access for the kids is ideal. For your two nights in the middle Keys—Marathon or nearby—there are a few oceanfront resorts that combine a tropical feel, beach access, and family-friendly amenities, often close to your budget of around $400/night.

Here are some recommended options for mid-Keys stays:

Tranquility Bay Beachfront Hotel & Resort (Marathon) – This is a resort-style property with direct beach access, pools, and watersports rentals. The vibe is tropical and relaxed, and families often enjoy the shallow beach areas for kids. Rates in June can approach your budget, so booking early is advisable.
Hawks Cay Resort (Duck Key) – A popular family-friendly resort with ocean and lagoon access. Offers pools, a kids’ club, water activities, and casual dining. It’s slightly more expensive than $400/night in peak season but sometimes deals are available midweek.
Islander Resort (Islamorada) – Offers direct beach access, a pool, and a tropical atmosphere. The resort is smaller, more intimate, and can feel very “island-like,” perfect for families wanting to relax and explore the area.
Holiday Inn Express & Suites Marathon – While not as luxurious, this can be a good budget-friendly option with easy access to local beaches and watersports, sometimes under $400/night.

Additional tips for your Florida Keys itinerary:

Book early: June is a popular time for families and resorts fill quickly.
Check beach access and safety: Some properties have calm water areas ideal for teens and younger swimmers.
Plan downtime: Two nights mid-Keys gives you time to explore the local shops, fish piers, and maybe even a short snorkeling excursion without feeling rushed.
Consider travel times: Driving from Miami to the Keys can take 2–3 hours to mid-Keys, so arriving mid-afternoon allows you to settle in and enjoy sunset on the beach.

For your last night near Miami Airport, you could stay in Miami Beach or closer to the airport in a hotel like the Miami Airport Marriott or Hyatt Regency for convenience before your flight home.

Overall, your itinerary seems balanced for a relaxing yet exploratory trip, giving teens time on the beach while also experiencing Key West’s unique culture.

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