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
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
7-night minimum 7-night minimum
Canalfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
This charming coastal retreat is the perfect hideout for a weekend at the pool or a quick trip to the beach. Within a five-mile radius of this cozy beachside cottage, you’ll find attractions such as Florida Keys Aquarium Encounters, Key Colony Beach Golf, and Sunset Park. Spend a day learning to snorkel the reefs, investigate the aquarium tou
7-night minimum 7-night minimum
Condo
- Marathon
Bathrooms 1 bath
This family-friendly home has everything you need for a trip to the Florida Keys: a private 35-foot dock space, Cabana Club membership, and classic home comforts! This canal front home for eight offers swimming, fishing, and more from your private dock! If you're in the mood for more traditional summertime fun, check out the Cabana Club's p
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
This gorgeous townhouse in the Florida Keys is the perfect paradise vacation for those wanting to experience true serenity. With unbeatable views, beach/dock access, a pool with a view, and a comfortable atmosphere filled with luxuries for everyone, you'll be sure to make memories that'll last a lifetime. Inside you'll find a bright int
7-night minimum 7-night minimum
Dry Lot
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
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 (33)
Canalfront
- Key Colony Beach
Bedrooms 2 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
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
KC202A - Ocean Oasis I Rating 5 (2)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 1 bath
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 (3)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
7-night minimum 7-night minimum
KC14B - Tropical Charm Rating 5 (6)
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Baths 1 half bath
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
7-night minimum 7-night minimum
MA203 - Ocean Isles #28 Rating 5 (14)
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
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
7-night minimum 7-night minimum
Canalfront
- Conch Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
This canal-front Keys charmer is your ticket to paradise! Along with scenic water views and direct access for kayaking or stand-up paddleboarding, you'll also enjoy membership privileges at the Cabana Club (across the street) featuring an oceanfront pool, a sandy beach area, and a snack bar. Public tennis courts and family facilities at First S
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 3 baths

Tell us what you're looking for and someone will contact you with available options.

I agree