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
Bougainvillea Villas – Marathon, FloridaEscape to the exclusive Bougainvillea Villas, a private, secured‑gated community in Marathon, FL, featuring just 14 stunning homes. This beautifully appointed house offers access to a shared bayside pool and fishing pier, creating the perfect setting for a tranquil waterfront retreat.🌴 Luxury & Com
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7-night minimum 7-night minimum
MA216 - Villa del Sol Rating 5 (3)
House
- Marathon
Bedrooms 3 bedrooms
Bathrooms 3 baths
Welcome to your tropical escape in the heart of the Florida Keys!Leave the everyday behind and settle into island time at this beautifully appointed retreat, where sunshine, adventure, and relaxation await. Whether you're looking for a peaceful getaway or an action-packed vacation, this is the perfect home base for experiencing all that the Flo
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7-night minimum 7-night minimum
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
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-
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DK27 - Key Lime Villa 7003 Rating 5 (62)
Canalfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 2 baths
Get a daily dose of sunshine and sea breezes at this waterfront retreat in Key Colony Beach. Primed for carefree coastal living, this breezy bungalow comes fully renovated throughout with all the modern comforts and essentials of home. Enjoy direct water access by way of private dock and take in the views on the covered lanai furnished for outdoor
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7-night minimum 7-night minimum
KC90 - Vitamin Sea Rating 5 (28)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
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
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Fall & Holiday Savings – Rates Reduced 15–20%!

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7-night minimum 7-night minimum
Oceanfront
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 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
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7-night minimum 7-night minimum
MA225 - Happy Daze Rating 5 (2)
Dry Lot
- Marathon
Bedrooms 3 bedrooms
Bathrooms 2 baths
Make this canal side Key Colony Beach rental your home away from home on your next vacation to the Florida Keys. Enjoy deluxe amenities throughout your rental and beach access through your Cabana Club membership, as well as access to a pool and bar area. Drop a kayak or canoe off the 35-foot dock behind your rental and paddle around your neighborho
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7-night minimum 7-night minimum
KC17 - Dream in the Keys Rating 5 (58)
Canalfront
- Key Colony Beach
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
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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
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
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Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

7-night minimum 7-night minimum
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Welcome to your waterfront escape in beautiful Key Colony Beach, where unforgettable days begin with ocean views and exclusive access to the Cabana Club!Whether you're planning a family vacation, a couples' retreat, or a relaxing getaway with friends, this inviting coastal home offers everything you need to experience the best of the Florid
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Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

7-night minimum 7-night minimum
KC110 - Key Colony Hide Away Rating 5 (11)
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 2 baths
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
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Fall & Holiday Savings – Rates Reduced 15–20%!

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7-night minimum 7-night minimum
MA222 - Seabreeze Haven Rating 5 (6)
Duplex/Townhome
- Marathon
Bedrooms 2 bedrooms
Bathrooms 1 bath
Make your next tropical getaway one for the ages at this Key Colony Beach vacation rental, a breezy waterfront home with access to the Cabana Club. Wind down with a bit of poolside relaxation, or grab a cocktail at its bar and lounge. From its beach, you could also sunbathe, build sand castles with your kids, or swim out into the ocean. The home
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Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

7-night minimum 7-night minimum
KC01 - Captain's Haven Rating 5 (85)
Canalfront
- Key Colony Beach
Bedrooms 3 bedrooms
Bathrooms 3 baths

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