Islamorada trip

Question

Trying to plan an Islamorada trip in April or early May and was looking for recs on waterfront places. Either resorts or rental condos would work. We would prefer a budget of $350 a night or under. Also any good fishing guides would be good, inshore or off shore. Any help wiuld be a huge help!!

Answer

Great plan — Islamorada is a beautiful spot and offers a lot for both relaxing and fishing. With your $350/night budget, you will have some decent options (though “budget” in the Keys still leans toward mid-tier), and there are several very good fishing guides for both inshore and offshore trips.

Where to stay (waterfront or close):

The Fisher Inn: One of the more affordable waterfront-adjacent places in Islamorada. According to local guides, it includes a sandy area, loungers, paddleboards, and bike rentals.
Blue Fin Inn: Mentioned in older accommodation guides; more of a motel style, but simple and key-style, and according to historic listings, quite budget-friendly.
Vacation Rentals / Condos: Look for condo units or small waterfront homes on Airbnb or VRBO around Islamorada (near upper or lower keys) — these may come in at or under $350 per night in early May, though availability and pricing will vary. (Because prices fluctuate a lot, I don’t have specific listings guaranteed under $350, but checking frequently and booking soon is key.)

Fishing charter recommendations:

Islamorada Fishing Guides & Charters: They offer a variety of trips including inshore/backcountry (flats, tarpon, redfish, etc.) and reef & offshore (sailfish, mahi, wahoo).
Spartan Charters: Excellent for both inshore (backcountry) and offshore. Their inshore trip (4–8 hours) is very good for flats species, and they also offer offshore trips targeting reef and deep-water species.
TAN MAN Charters: Based out of Bud n’ Mary’s Marina, they specialize in offshore sportfishing — great if you’re interested in mahi, tuna, sailfish, and big-game action.
FireFly Charters (Capt. Luis Cortes): Very well regarded for inshore fishing, especially fly-fishing/light tackle. Species include tarpon, bonefish, snook, permit, and more.
Spartan Lobster Trip: For something different, Spartan Charters also offers a “lobster fishing” / bully-netting trip in the shallow flats — plenty of fun, especially if you want something more than just traditional fish.

Tips for planning your trip:

Book your accommodation early: April and early May are popular in the Keys, and budget waterfront places go quickly.
Reserve your fishing charter in advance: Good guides will fill up, especially for the half-day trips you’re considering. Be clear about the kind of trip (inshore or offshore) when booking.
Bring sun protection, snacks, and water for fishing trips: Flats and offshore days can be long and sunny.
If doing lobster / bully-netting, double check local regulations (season, size limits, permits) — your charter guide will typically help you with this.

In summary: For your budget, The Fisher Inn is probably your best resort-ish option, and for fishing, both Islamorada Fishing Guides & Charters and Spartan Charters provide excellent half-day inshore and offshore experiences. If you want a more adventurous or different trip, TAN MAN and FireFly are also strong choices.

Islamorada trip

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