Don't know anything about FL - tasked with finding a place t

Question

Hi all, my elderly father has tasked me with finding a ~1 month rental this winter somewhere in FL so that my entire family (spread around the country) can come visit and we can see one another. Several adults, one elderly man, and some children. None of my family is familiar with FL at all, and I've never even been there. I'm here to see if anyone has any suggestions of what places I should look at, given our wishlist, which is fairly short:

1) Warm/hot in February. I naively assumed the entire state would fit the bill here, but was recently told by someone that that is not the case. Ideally, it would be sufficiently warm to enter the ocean/swim in a pool in Feb. Does that limit me to only south FL?

2) Walkable urban core. My father no longer drives and wants to be able to walk around to, you know, shops, restaurants, bars, that type of thing. I have read that these are rare in FL, but basically we don't want to rent a house in a suburb and have to drive everywhere. It doesn't have to be a major downtown (although it could be), but any type of that mini-downtown/touristy area. It's fine if it is touristy, since we'll be tourists!

3) Near the coast. We probably can't afford to rent a place directly on the coast, but ideally we'd be walkable to a beach, or at least a short drive/bike ride. So, basically not central FL.

Would love any suggestions folks have - and thanks so much in advance. If I'm missing any integral info, let me know and I'll add it to the post. Thanks!

Answer

Florida in February is generally warm, but the southern part of the state is more reliably hot enough to swim comfortably in the ocean or enjoy outdoor pools. Central and northern Florida can be cooler, with average highs in the 60s–70s°F, which might not be ideal for swimming. South Florida, including areas like Miami, Fort Lauderdale, and the Florida Keys, will give you the warmest and most reliable weather for ocean swimming.

Based on your criteria—walkable urban core, proximity to the coast, warm weather, and a variety of activities for adults and children—there are several options that could suit your family:

Miami Beach / South Beach: Very walkable with restaurants, shops, bars, and iconic beaches. Plenty of short-term rentals and condos available. Ocean is warm enough in February. Tourist-oriented but lively.
Fort Lauderdale: Walkable areas like Las Olas Boulevard provide shops, dining, and easy access to beaches. Slightly less hectic than South Beach, family-friendly, and good for multi-generational groups.
Naples: Southwest Florida town with upscale shopping, restaurants, and beaches. More relaxed and quieter than Miami or Fort Lauderdale. Walkable downtown area, and the beaches are beautiful.
Key West: Unique island feel, extremely walkable with shops, restaurants, and bars. Beaches are smaller but accessible. Warmest part of Florida in February, perfect for a long stay and multi-generational visiting.
St. Pete Beach / Clearwater Beach: Along the Gulf Coast, with good weather and a vibrant but manageable town center. Walkable streets near the beach, plenty of dining options, and suitable for family visits.

Other considerations:

Vacation rentals or condos are generally better than hotels for a month-long stay, giving the family space to gather and cook meals.
Look for properties labeled “walkable to beach” or “downtown condo” to ensure minimal driving needs.
If your father cannot drive, proximity to grocery stores, pharmacies, and medical services is also important—choose a central area rather than a remote beach house.
February is peak season in south Florida, so book early to secure larger rental spaces and reasonable pricing.

In summary, for warm swimming weather and a walkable, coastal urban core, South Florida—particularly Miami Beach, Fort Lauderdale, and the Keys—offers the best combination of amenities, beaches, and entertainment for a multi-generational month-long stay. Naples and St. Pete Beach are excellent if you prefer a quieter, slightly less touristy environment with easy beach access.

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