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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Properties Available 100 properties available
Experience the essence of island living at Sea Pointe & Canal-Side Charisma, where both halves of this stunning waterfront duplex are exclusively yours. Perfect for families or groups of friends, this tropical retreat offers the best of Key Colony Beach with spacious accommodations, private amenities, and access to resort-style perks. Nestled a
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 4 bedrooms
Bathrooms 4 baths
Welcome to your oceanfront retreat in Duck Key, FL! This charming townhouse offers a cozy and inviting atmosphere, perfect for a family getaway or a relaxing retreat. With stunning ocean views, you'll feel like you're in paradise from the moment you arrive. This family-friendly townhouse features a well-equipped kitchen with modern applianc
Dry Lot
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Completely remodeled by HGTV, this home boasts beautiful furnishings, perfect interior design, and timeless decor that will have you feeling right at home the moment you step through the door! The full kitchen is complete with stainless steel appliances, marble countertops, and a massive island, so cook up your favorite recipes with ease. Though th
7-night minimum 7-night minimum
MA88 - La Pirata Rating 5 (16)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Welcome to your tropical escape in Marathon, FL! This bright and spacious condo combines comfort with adventure, making it the perfect retreat for families, couples, or solo travelers. With a king bed and a double bed, the home easily accommodates your group, while modern amenities—like a fully equipped kitchen (fridge, stove, oven, and dishw
7-night minimum 7-night minimum
MA226 - Keys Therapy Rating 5 (3)
Dry Lot
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Boasting some of the great fishing in the world, beautiful and sparkling beaches, and warm weather, Marathon is widely considered the best destination in Florida! This captivating, snowbird-friendly home is located near plenty of dining options and less than two miles from the Florida Keys/Marathon International Airport. This relaxing neighborhood
7-night minimum 7-night minimum
MA163 - Sea Salt Harbor Rating 5 (13)
House
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 2 baths
Located right on the water, this charming house offers the quintessential South Florida experience. For the fishing enthusiast, the highlight is the private dock—nestled on one of the few flow-through canals in Marathon. Bring your own boat and enjoy immediate access to the gulf or the sea. After a day on the water, rinse off at the outdoor s
7-night minimum 7-night minimum
MA105 - Casa Palmera Rating 5 (8)
Canalfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Escape to the sunny Florida Keys with this nautically-themed Marathon vacation rental! Complete with a private deck and free Wi-Fi, this charming duplex is the perfect antidote to beat those winter blues. If you prefer to travel by land, you're only five miles from the mangrove swamps of Curry Hammock State Park, where you can rent kayaks, watc
7-night minimum 7-night minimum
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
This bright and attractive home is right on the canal with a 70-foot boat dock, a covered balcony with partial ocean views, and an outstanding interior featuring an open floorplan and nine-foot ceilings that you will love. The living area features lots of comfortable furniture surrounding a TV, an ideal place for entertaining guests or kicking back
7-night minimum 7-night minimum
MA127 - Marathon Majesty Rating 5 (10)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Nestled in the heart of Marathon, FL, this charming house offers a serene retreat with stunning water views and a private dock along the canal. The abundance of natural light throughout the home creates a warm and inviting atmosphere, perfect for unwinding and enjoying the picturesque surroundings. With a double driveway, there's ample parking
7-night minimum 7-night minimum
MA223 - Seaside Manor Rating 5 (3)
Canalfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Come and experience everything the Sunshine State has to offer when you book this pleasant waterfront duplex! This splendid home away from home oozes a bohemian tropical vibe and enjoys an unbeatable location right behind Marathon International Airport and just a stone's throw from US 1. There's plenty to explore close to home. You can walk
7-night minimum 7-night minimum
MA172 - Bohemian Haven Rating 5 (2)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
With a wonderful location and a private sandy beach just steps away, this family-friendly townhouse is all set up for your beach getaway. Step inside and you'll be greeted by the charming full kitchen, remodeled as of spring 2021 and featuring granite countertops and full-size appliances for your cooking projects. Central air-conditioning will
Oceanfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath

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