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Islamorada Home Rentals

A 3-bedroom base for a tournament week in Islamorada

If you want a three-bedroom house in Islamorada for a tournament week and there are up to eight of you, the one we rent is The Oasis: three bedrooms and four beds split across a main house and a guest house on 2.75 acres of private oceanfront, with 200 feet of sandy beach and views out to Alligator Reef Light. We're Doli and Mark, we've been hosting here for more than twelve years, and this is the only home we rent. So this isn't a roundup. It's an honest account of whether our house fits the way a fishing crew actually uses a week, and what you'll want to sort out separately.

Why the split layout matters when half the house leaves at four in the morning

The three bedrooms aren't in one building. The main house holds a king bedroom with a Tempurpedic adjustable bed, a bath and a half, a full kitchen and a wrap-around porch. The guest house holds the other two bedrooms (a queen, and a queen/full), its own bath, its own full kitchen, and a living room looking at the ocean.

Two kitchens and two front doors is the whole argument for this house during a tournament. The anglers can be up making coffee, loading the truck and slamming screen doors while whoever is not fishing that day sleeps through it in the other building. Nobody is negotiating for counter space at 4am. The dishwasher, washer and dryer mean the salt-soaked shirts from day one are clean for day three, and the ice maker matters more than it sounds like it should when you're filling anything before you leave.

Eight is the ceiling. Three and a half bathrooms across the two buildings is generous for that number, which is the quiet reason big groups stop arguing here.

Where this puts you among the marinas

We're in the heart of downtown Islamorada, on Upper Matecumbe, around mile markers 81 and 82. The practical consequence: the charter docks are all a short run up or down the Overseas Highway rather than a commute. Bud N' Mary's sits oceanside at MM 79.8. Robbie's is a little further south around MM 77.5, and Bud N' Mary's is roughly a five-minute drive from it. Whale Harbor, with its lighthouse out front, is just north at MM 83.4. Anywhere in this stretch keeps you inside ten minutes of the marinas, which is the argument against basing yourself in Key Largo, half an hour up the road.

Tournament venues move around the island. The Islamorada Sailfish Tournament runs in December, the Fish for Holly Sailfish Tournament fishes out of the Islander Resort in January, the Junior Sailfish Tournament for the 16-and-under crowd holds its events at the Sandbar at Whale Harbor, and the Gold Cup Tarpon Tournament works out of the Lor-e-lei in June. The Islamorada Fishing Club is over on Madeira Road. All of that is within a few minutes of here. Check your own tournament's captains' meeting location when you register, because venues and dates shift year to year.

Coming in from Miami International, the drive down is roughly an hour and a half to two hours depending on how US-1 behaves. From Fort Lauderdale, closer to two. From Marathon Airport, you're driving north on US-1 for something under an hour.

Dock access, and the question to ask us first

The honest answer about your boat is that it depends on your boat, and it's a conversation to have with us before you book rather than something to read off a page. Trailer parking, tie-up, draft, where you'll clean fish, where you'll put bait and gear: message us with your rig and your dates and we'll tell you straight what works here and what you'll want to arrange at a marina. We'd rather lose a booking than have a captain arrive and discover a mismatch on the morning of a shootout.

What we can say plainly: the property is beachfront and oceanfront, directly on the Atlantic, with free parking and a gated entrance. The gate is worth more than it sounds during a tournament, when there's expensive tackle sitting in a truck bed overnight.

What the house is for at the end of a long day on the water

The heated saltwater infinity pool faces open Atlantic with nothing in the way. There's a BBQ area, and if the day went well you'll want it. We keep spices in both kitchens, so you're buying fish and not a cabinet's worth of groceries. There are over a hundred palm trees on the property and more than sixty of them are lit after dark, which turns the lawn into somewhere people actually sit rather than pass through.

For the crew members who came along but aren't fishing every day: four kayaks and two paddleboards go straight off our own sand, and six good bikes cover Upper Matecumbe without anyone moving a truck. Bocce and cornhole live on the grass. Dolphins pass offshore often enough that it stops being an event by about Wednesday.

On land, Bayside Gourmet is a counter-service place with six tables inside, mostly locals, and a grouper Reuben that justifies the queue. Mangrove Mike's Cafe at MM 82.2 bayside has been voted Islamorada's best breakfast since 1998, which is the one to know when the boat leaves late. Whistle Stop at MM 82.6 oceanside is among the few kitchens still serving after nine, so it's where you end up when the day runs long. The Green Turtle Inn has been a local landmark since 1947. Pierre's sits on the beach at MM 81.6 with the dining room upstairs. Italian Food Company and a couple of breweries and galleries are walkable or an easy ride from the gate, and Publix is less than a mile off.

Dogs, and the rest of the practical stuff

Dogs are welcome for a $350 fee, and the yard is fenced and grassy, which is the part that matters if your dog is spending the day at the house while you're offshore. There's a Tesla charger and a NEMA 14-50, so an EV in the driveway isn't a planning problem. The Wi-Fi is enterprise-grade and covers the whole estate, which matters if someone in the group is working remotely or you're uploading photos for a leaderboard.

Our reviews run 5-star across 126 and counting, 37 of them on this listing. That's twelve years of answering texts at odd hours, which is more or less what a tournament week asks of a host.

Before you book

Four things to settle with us, in this order:

  • Your dates. Tournament weeks book early here, and we only have one house. Ask about availability and minimum stay first, because everything else is academic if the week is gone.
  • Your boat. Length, draft, trailer, and whether you plan to keep it on site or at a marina. Tell us before you reserve.
  • Fish handling. Cleaning, bait and ice storage, and where gear goes overnight. Ask us and we'll tell you what the property supports and what the marinas near MM 77 to 84 handle better.
  • Who's sleeping where. Eight guests across three bedrooms and four beds works beautifully for a crew of couples or a mixed group that doesn't mind the main-house-and-guest-house split. Nine people does not fit, and it's better to know that now.

Message us with your tournament and your dates. We'll tell you honestly whether this house is the right base for your week.

Frequently asked questions