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 89 properties available
A treasure trove of tropical delights awaits at this breezy, two-bedroom Keys hideaway. Located on Marathon's quiet, Boot Key, you'll be within walking distance of popular Sombrero Beach and enjoy ocean views from home with direct canal access via a private dock. Other features include a private pool with pool spa and a patio furnished for
7-night minimum 7-night minimum
MA150 - Pirate's Booty Rating 5 (36)
Canalfront
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Spend some time in the Florida Keys at this three-bedroom, canalside rental with a furnished and covered patio, private pool, a 75-foot dock, and plenty of room inside the home for up to seven guests (six comfortably). The family dog is also welcome to join you here for an additional nightly fee. This vacation rental is conveniently located right o
7-night minimum 7-night minimum
MA60 - Magic in Marathon Rating 5 (85)
Canalfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Oceanfront Villa Nadia offers a laid-back Keys escape with beautiful water views and an unbeatable marina setting in Marathon. This spacious 3-bedroom, 2.5-bath condo blends comfort and coastal charm, giving up to 8 guests plenty of room to relax after days spent on the water or exploring the islands.Inside, the home is designed for easy vacation l
7-night minimum 7-night minimum
Oceanfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
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
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
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 (7)
Canalfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
** This vacation home has a 7-night minimum stay. The City enforces this, and we cannot make any exceptions. Make yourself at home and enjoy a thrilling fishing trip at this two half-duplex, studio apartment 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 wel
7-night minimum 7-night minimum
Canalfront
- Conch Key
Bedrooms 1 bedroom
Bathrooms 1 bath
Escape to this stunning, newly constructed 4-bedroom, 3-bath home featuring two king ensuite bedrooms and breathtaking views. Located on Coco Plum in Marathon, FL, this Coastal Chic Keys retreat offers the perfect waterfront escape. Step inside and enjoy a private balcony overlooking the pool and canal, setting the tone for a serene and memorable s
7-night minimum 7-night minimum
MA220 - Coco Plum Oasis Rating 5 (9)
Canalfront
- Marathon
Bedrooms 4 bedrooms
Bathrooms 3 baths
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 (46)
House
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
One half of this wonderful waterfront duplex is all yours for an unforgettable Florida Keys getaway! 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 ten
7-night minimum 7-night minimum
KC203B - KCB Canal Livin' Rating 5 (30)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 3 baths
Welcome to your perfect Florida Keys escape! Nestled along a peaceful canal in the heart of Key Colony Beach, this inviting waterfront home offers everything you need for an unforgettable island vacation. From boating and fishing adventures to relaxing beach days, you'll enjoy the best of the Keys right at your doorstep.One of the home's st
7-night minimum 7-night minimum
KC14B - Tropical Charm Rating 5 (14)
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Baths 1 half bath
Your Private Poolside Escape in MarathonEscape to paradise at this beautifully updated 3-bedroom, 2-bath vacation home in the heart of Marathon, Florida! With a private pool, spacious outdoor entertaining areas, and plenty of family-friendly amenities, this tropical retreat is the perfect home base for your Florida Keys getaway.Comfortable Island L
7-night minimum 7-night minimum
MA225 - Happy Daze Rating 5 (2)
Dry Lot
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths

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

I agree