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
It's all about the outdoor living at this lovely, central Keys getaway! Your home away from home on Marathon features a private boat dock, pool, and pool table - and you’re walking distance to Sombrero Beach. Start your day on your wraparound deck, iced coffee in hand, enjoying that lovely water view. Take your time - you’re in the
7-night minimum 7-night minimum
MA135 - The Anchor House Rating 5 (50)
Oceanfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
This stunning oceanfront property offers breathtaking views that provide the perfect backdrop for your vacation. The waterfront deck feels like a mini resort paradise with tropical thatched awnings, swaying palm trees, and classic beach-style furnishings. Make the most of your trip with access to the Cabana Club, offering beach access, a heated swi
7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 4 bedrooms
Bathrooms 4 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
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
*Please note that this home only allows minimum stays of 7 nights or longer. This is enforced by the city and we cannot make any exceptions. Fisherman's Hideaway is the perfect home base for your next fishing trip to Conch Key! This snowbird-friendly studio comes with access to open water via the deepwater docking out back, as well as use of a
7-night minimum 7-night minimum
Canalfront
- Conch Key
Bedrooms 1 bedroom
Bathrooms 1 bath
Escape to this charming coastal condo in Ocean Isles Fishing Village—your perfect Florida Keys retreat.Guests love the warm, homey feel of this two-story condo, with comfortable living spaces on both levels—each with a smart TV, giving everyone room to relax. The open layout includes a fully equipped kitchen, air conditioning, and an in
7-night minimum 7-night minimum
MA209 - Overseas Beauty Rating 5 (28)
Dry Lot
- Marathon
Bedrooms 1 bedroom
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 (5)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 1 bath
Paradise truly abounds at this modern waterfront masterpiece in the heart of the Florida Keys. Designed with marble finishes, soaring ceilings, and walls of sunlight, Tropical Delight invites you to relax in style while enjoying the laid-back island lifestyle. ✨ Interior Highlights Step into the open-concept living space, where the living room, din
7-night minimum 7-night minimum
MA183 - Tropical Delight Rating 5 (18)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 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
Nestled in the heart of Marathon, FL, this charming waterfront duplex offers the perfect blend of comfort, convenience, and coastal beauty. With two bedrooms and one bathroom, the thoughtfully designed sleeping arrangements include a queen bed, twin-over-double bunk with a twin trundle, and a queen sleeper sofa in the living room, making it an idea
7-night minimum 7-night minimum
MA222 - Seabreeze Haven Rating 5 (6)
Duplex/Townhome
- Marathon
Bedrooms 2 bedrooms
Bathrooms 1 bath
This charming Key West style home features a beachy and clean modern interior decor that will let you truly unwind and feel as you're already at the beach! It's fully gated for privacy and boasts two covered porches equipped with comfortable seatings. The property has a large yard with beautiful mature trees and established landscaping. The
7-night minimum 7-night minimum
MA81 - Trout Key Rating 5 (66)
Canalfront
- Marathon
Bedrooms 1 bedroom
Bathrooms 1 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
7-night minimum 7-night minimum
MA147 - Yellowtail House Rating 5 (18)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly

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