Marathon & Middle Keys Vacation Rentals
Marathon and the Middle Florida Keys offer a relaxed, centrally located island escape with a variety of waterfront homes, canal-front retreats, and coastal-style condos designed for comfort and convenience. Choose from vacation rentals featuring multiple bedrooms, full kitchens, outdoor living spaces, and private docks—ideal for families, couples, and group getaways. Many Marathon and Middle Keys rentals include sought-after amenities such as boat access, private pools, and scenic views of the Atlantic Ocean or Florida Bay across Marathon, Key Colony Beach, Duck Key, Conch Key, and Layton.
Located between the Upper and Lower Keys, the Middle Keys—including Marathon, Key Colony Beach, Duck Key, Conch Key, and Layton—provide a balanced blend of accessibility, natural beauty, and laid-back island living. With easy access to both the ocean and the bay, this area is a favorite for boating, fishing, snorkeling, and diving. A mix of oceanfront and bayfront properties, quiet neighborhoods, and family-friendly accommodations make Marathon and the Middle Keys an ideal base for exploring the Florida Keys.
Why Stay in Marathon & the Middle Keys?
Marathon offers a central location within the Florida Keys, making it easy to explore in either direction while still enjoying a quieter, more relaxed atmosphere. Known for its family-friendly appeal and convenient access to activities, Marathon is a great choice for guests who want a well-rounded island experience.
The surrounding Middle Keys communities—including Key Colony Beach, Duck Key, Conch Key, and Layton—offer a mix of peaceful waterfront neighborhoods and resort-style settings, ideal for travelers seeking space, comfort, and a strong connection to the water.
Waterfront Living & Boating Access
One of the biggest draws of Marathon and the Middle Keys vacation rentals is the access to the water. Many homes feature private docks, canal access, and quick routes to both offshore and backcountry waters, making it easy to bring a boat or book a local charter.
Outdoor living is central to the experience, with spacious decks, shaded patios, and private pools offering the perfect place to relax after a day on the water. Whether you're fishing, boating, or simply enjoying the view, these homes are designed for easy island living.
Plan Your Middle Keys Getaway
From boating and fishing to relaxing poolside and exploring nearby islands, Marathon and the Middle Keys offer a versatile Florida Keys experience. With comfortable homes, a convenient central location, and direct access to everything that makes the Keys special, vacation rentals in Marathon and the surrounding communities provide the perfect setting for your next coastal escape.
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Find a relaxing respite for days spent fishing, boating, and swimming at this two-story condo in Marathon, the perfect setting for embracing the Florida Keys lifestyle. Ocean Isles Fishing Village is ideal in many ways, with grounds including a waterfront swimming pool and sundeck. One small kayak and three paddle boards so you can easily get out o
Create unforgettable memories in the heart of the Florida Keys with a stay at this delightful waterfront townhouse on picturesque Duck Key. Set along a serene canal with easy proximity to nearby restaurants, spas, and excursions, this home offers everything you need for a relaxing and adventure-filled getaway. Step inside to find a bright, coastal-
Stylish seaside studio situated near the northern end of Marathon, you'll enjoy a convenient location for all your favorite Florida Keys activities - both on and off the water. Additional on-site perks including an oceanfront pool and shady, palapa-style picnic benches let you indulge in waterfront leisure just steps from your front door. Some
What are you waiting for? The island retreat of your dreams awaits at this marvelous Marathon condo! Your days under the sun can be spent in the sand, just steps from your front door. When you’re not building sandcastles or collecting seashells, cool off in the sparkling shared pool or fire up the grill for a laid-back cookout. 🌴 Why You&rsq
This home features impressive sunset views over the open Gulf! The whole house is set up for a beach-loving family. Located on a completely fenced 1/4 acre property, this home allows plenty of parking for a boat trailer. The new dock can fit a large boat, and the large swimming pool and tropical hut are perfect for relaxing after boating. Guests ca
Welcome to your deluxe beach getaway here in Key Colony Beach, where you can enjoy exclusive access to the Cabana Club! With waterfront views, you'll have the perfect setting for a relaxing vacation. This property features a patio with a gas grill, ideal for alfresco dining while enjoying the ocean breezes. Inside, the well-equipped, full kitch
Escape the everyday and experience the extraordinary when you book this fantastic vacation rental in the beautiful Florida Keys. Spend your days on the water by going paddleboarding, swimming, fishing, or touring the area to discover delightful attractions. Florida Keys Aquarium Encounters, Key Colony Beach golf, Hammock State Park, Turtle Hospital
A private paradise awaits at this oceanside, canal-front stunner! Along with direct, deep-water canal access and private boat moorage, this custom delight boasts highlights like a waterfall-fed pool, a thatched palm palapa hut furnished for outdoor living, and a deluxe outdoor kitchen outfitted with a grill, a griddle, and a sink. Additional featur
Make your next trip to the Florida Keys the best one yet with this Key Colony beach home, which offers a Cabana Club membership, access to a private beach, and private 35-foot dock for the ideal Florida vacation. This canal-side home is perfect for boaters and fans of watersports, with easy access to scuba diving, snorkeling, and sport fishing! Bac
This lovely waterfront duplex hosting lush interiors and incredible water views will surely be the highlight of your next Key Colony Beach escape! Ideally located for fun and recreation, you’ll find Key Colony Beach Golf, Sunset Park, and Florida Keys Aquarium Encounters all within a two-mile radius. Spend a day playing a leisurely round of g
Located in Marathon, FL, this charming condo is just a stone's throw away from the renowned Sombrero Beach, one of the top-rated beaches in the state. With grocery stores, restaurants, and various retail shops within a two-mile radius, convenience is at your fingertips. Whether you're into fishing, diving, snorkeling, or simply soaking up t
This spacious home offers a great ocean view and is located on a canal with a dock and room for a boat up to 24 feet in length. Spread out over two levels, this spacious getaway features a full kitchen, a lower-level kitchenette, a patio, and a private, outdoor pool. This rental is an easy walk or bike ride to Sombrero Beach as well as the Turtle H
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