Marathon & Middle Keys Vacation Rentals

Browse Marathon FL vacation rentals and Middle Keys vacation rentals with Seven Keys Vacations and stay close to the center of the Florida Keys. This area is a favorite for guests who want easy access to both the Upper and Lower Keys, while still having plenty to enjoy right nearby. Our Middle Keys rentals include waterfront homes, canal-front retreats, coastal condos, private pool homes, and boat-friendly stays across Marathon, Key Colony Beach, Duck Key, Conch Key, and Layton.

Marathon has a practical, easygoing island feel that works especially well for families, fishing trips, boating vacations, and longer stays. Spend the day at Sombrero Beach, walk or bike part of the Old Seven Mile Bridge, visit The Turtle Hospital, head out on a fishing charter, or come back to a rental with a pool, dock, and space to settle in.

Find the Right Middle Keys Rental for Your Trip

The Middle Keys are a strong choice for travelers who want a convenient home base without giving up the water. Many Marathon vacation rentals offer canal access, private docks, outdoor dining areas, and easy routes to the ocean or bay. If boating is part of your trip, browse our vacation rentals with boat docks. Guests looking for extra space to relax can also explore Florida Keys rentals with private pools, homes with an ocean view, or oceanfront rental homes.

Each Middle Keys community brings something a little different. Marathon is the most central and activity-friendly, Key Colony Beach is peaceful and residential, Duck Key has a more resort-style feel, and the smaller nearby islands offer a slower pace for guests who want quieter surroundings. If you are still comparing areas, you may also want to browse Islamorada vacation rentals, Lower Keys vacation rentals, or our full collection of Florida Keys vacation rentals.

Planning more than a quick trip? The central location makes this area especially helpful for longer stays. Explore weekly rentals in the Florida Keys or monthly rentals in the Florida Keys if you want more time for beach days, boating, fishing, remote work, and unhurried island living.

Browse available Marathon and Middle Keys vacation rentals below and book direct with Seven Keys Vacations for a more personal, locally focused rental experience.

Marathon FL vacation rentals in the Middle Keys with turquoise water, palm trees, waterfront homes, and boating access

Properties Available 98 properties available
This charming oceanfront two story townhouse offers uninterrupted water views and the laid-back luxury that Duck Key is known for. Perfect for families seeking a peaceful retreat with easy access to world-class boating, fishing, and waterfront relaxation. Step inside to a bright, coastal-inspired living space with comfortable seating and large wind
Canalfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Welcome to Island Time at Cocoa Plum, your serene escape in the heart of the Florida Keys. Nestled in the highly coveted Cocoa Plum area of Marathon, this spacious 3-bedroom, 2-bath condominium blends coastal luxury with laid-back island living—perfect for families, couples, and adventure-seekers alike. You’ll be just 0.5 miles from Coc
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
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-
DK27 - Key Lime Villa Rating 5 (40)
Canalfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
Canalfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
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
MA88 - La Pirata Rating 5 (39)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Get a taste of the coastal lifestyle in Key Colony Beach when you make this newly updated home your retreat away from home! Sitting on the area's unique canal system, enjoy your favorite drinks on the patio with views of the water. Bright and spacious, the interior features all of the comforts of home. Though it will be hard to leave the comfor
KC73 - R & R Retreat Rating 5 (33)
Canalfront
- Key Colony Beach
Bedrooms 2 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
MA223 - Seaside Manor Rating 5 (4)
Canalfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Fisherman's Retreat is the perfect home base for your fishing trip; it's conveniently located in the fishing community of Conch Key, where you can enjoy the use of the deepwater docking out back with easy access to the open water as well as the fish cleaning table and bait freezer. These two half-duplex, studio apartments may be rented indi
Canalfront
- Conch Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
I🌊 WHY YOU'LL LOVE IT Wake up each morning to canal views from your private patio, sip coffee in a swinging chair, and feel the gentle Florida Keys breeze set the tone for the day. This villa isn’t just a place to stay — it’s your gateway to the laid-back, sun-soaked lifestyle that makes the Keys unforgettable. • Waterfr
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
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
An escape to Marathon never looked so good! Yellowtail House is perched in the heart of all the actions, so you will have no delay in checking out pristine beaches, local attractions, ample shopping options, and an abundance of tasty restaurants within walking distance of home base. And, when you really want to indulge in a bit of coastal adventure
MA147 - Yellowtail House Rating 5 (10)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Spend your days soaking up the sun and cruising the Florida Keys when you escape to this light-filled, waterfront home, beautifully situated among the canals and palms of Key Colony Beach. Enjoy your own 60-foot dock, a canalside patio, and a wonderful location for golfing, fishing, and beach-going. This single-story home sits at the edge of an oce
KC100 - Breezy Keys Rating 5 (8)
Canalfront
- Key Colony Beach
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly

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