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 91 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
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7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 4 bedrooms
Bathrooms 4 baths
Perched on one of the many canals in Key Colony Beach, you'll discover your favorite escape! Full of sunlight and color, this lovely duplex is a place of warm memories and utter peace. Spend time with your favorite people while enjoying the living room's comfortable seating and Smart TV. The home's kitchen radiantly gleams with its gran
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
7-night minimum 7-night minimum
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
Relaxation comes easy at this canal-side home in the private Yacht Harbor neighborhood in Marathon. A private, sparkling pool completes your resort-style outdoor oasis. A screened patio at the rear of the house offers a relaxed social space with a pair of loungers and a high-top table. Sunbathe on lounge chairs between refreshing dips. You can soak
7-night minimum 7-night minimum
MA118 - Coral Cove Rating 5 (43)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Escape to this charming townhouse in the heart of Hawks Cay Resort, where breathtaking water views greet you from the deck, balcony, and patio. Relax in the coastal breeze as you unwind with the soothing sounds of the waves—your perfect island getaway awaits. Step inside to find a well-equipped kitchen complete with a fridge, stove, oven, dis
Canalfront
- Duck Key
Bedrooms 3 bedrooms
Bathrooms 3 baths
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
7-night minimum 7-night minimum
KC73 - R & R Retreat Rating 5 (49)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
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
7-night minimum 7-night minimum
MA186 - Ocean Isles 50 Rating 5 (15)
Condo
- Marathon
Bathrooms 1 bath
With fun beach decor, a bright interior, and plenty of room for everyone to spread out, no one will have trouble slipping into relaxation mode. Step out to your balcony with a fresh cup of coffee each morning or a glass of wine in the evening and breathe the salty air. After a full day of fun in the sun, the open layout of the full kitchen, dining
DK12 - Harbor Villa 7103 Rating 5 (84)
Dry Lot
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Plein Air Point is the perfect combination of modern elegance and laid-back Keys living. Nestled at the end of Patricia Lane in Marathon, it’s surrounded on three sides by a Florida land preserve, a deep-water canal, and the Gulf of Mexico. This is a wildlife refuge teeming with birds and assorted aquatic life. Plein Air Point is a place to b
7-night minimum 7-night minimum
MA68 - Plein Air Point Rating 5 (165)
Oceanfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
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
7-night minimum 7-night minimum
MA221 - The Tropical Cove 329 Rating 4.9 (24)
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 1 bath
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
7-night minimum 7-night minimum
KC202B - Ocean Oasis II Rating 5 (20)
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 2 baths
Escape to this waterfront, two-bedroom, one-and-a-half-bath Duck Key villa boasting breathtaking sunset views from your patio and balcony! This two-story end unit features nautical-inspired design elements paired with lots of natural light and privacy. Pick up a local fishing kit or bring your own, then spend leisurely afternoons fishing from the s
DK21 - Palm Breeze - Villa 5030 Rating 4.9 (40)
Oceanfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath

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