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Marinas pop up every mile or so in the Islamorada area, so finding a rental or tour is no problem. Robbie's Marina is a prime example of a salty spot where you can find it all—from fishing charters and kayaking rentals to lunch and tarpon feeding.
Bump & Jump. Fishing and deck boats rentals (from 15 to 29 feet) are $165 to $495 per day, and weekly rates go from $745 to $2,490. MM 81.2 OS, 81197 Overseas Hwy., Upper Matecumbe Key, Islamorada, FL, 33036. 305/664–9404 or 877/453–9463. www.keysboatrental.com.
Houseboat Vacations of the Florida Keys. See the islands from the comfort of your own boat (captain's cap optional). The company maintains a fleet of 42- to 55-foot boats that accommodate up to 10 people and come outfitted with everything you need besides food. (You may provision yourself at a nearby grocery store.) The three-day minimum starts at $1,112; one week costs $1,950 and up. Kayaks, canoes, and skiffs suitable for the ocean are also available. MM 85.9 BS, 85944 Overseas Hwy., Plantation Key, Islamorada, FL, 33036. 305/664–4009. www.floridakeys.com/houseboats.
Nauti-Limo. Captain Joe Fox has converted the design of a 1983 pink Caddy stretch limo into a less-than-luxurious but certainly curious watercraft. One-hour tours start at $60 per couple. The seaworthy hybrid—complete with wheels—can sail with the top down if you're in the mood. Only in the Keys! MM 82 BS, Lorelei Restaurant & Yacht Club, Upper Matecumbe Key, Islamorada, FL, 33036. 305/942–3793. www.nautilimo.com.
Robbie's Boat Rentals & Charters. This full-service company will even give you a crash course on how not to crash your boat. The rental fleet includes an 18-foot skiff with a 60-horsepower outboard for $150 for four hours and $200 for the day to a 23-foot deck boat with a 130-horsepower engine for $185 for a half day and $235 for eight hours. Robbie's also rents fishing and snorkeling gear (there's good snorkeling nearby) and sells bait, drinks and snacks, and gas. Want to hire a guide who knows the local waters and where the fish lurk? Robbie's offers offshore-fishing trips, patch-reef trips, and party-boat fishing. Backcountry flats trips are a specialty. MM 77.5 BS, 77522 Overseas Hwy., Lower Matecumbe Key, Islamorada, FL, 33036. 305/664–9814 or 877/664–8498. www.robbies.com.
Treasure Harbor Marine. Captains Pam and Pete Anderson provide everything you'll need for a bareboat sailing vacation at sea. They also give excellent advice on where to find the best anchorages, snorkeling spots, or lobstering sites. Vessels range from a 19-foot Cape Dory to a 41-foot Morgan Out Island. Rates start at $125 a day; $500 a week. Captained sails are $550 a day, $3,250 a week aboard the 41-footer. Marina facilities are basic—water, electric, ice machine, laundry, picnic tables, and restrooms with showers. A store sells snacks, beverages, and sundries. MM 86.5 OS, 200 Treasure Harbor Dr., Plantation Key, Islamorada, FL, 33036. 305/852–2458 or 800/352–2628. www.treasureharbor.com.
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