Marathon Vacation Rentals

Why rent a simple hotel room when you can rent through Owner Direct Vacation Rentals and enjoy the comforts of your own vacation rental home, condo rental accommodation or chalet rental lodging in Marathon, Florida. Known as the "Heart of the Florida Keys," Marathon has blossomed into a small city centered on the island of Vaca Key at the midpoint of the Keys island chain. It boasts many... read more
Why rent a simple hotel room when you can rent through Owner Direct Vacation Rentals and enjoy the comforts of your own vacation rental home, condo rental accommodation or chalet rental lodging in Marathon, Florida. Known as the "Heart of the Florida Keys," Marathon has blossomed into a small city centered on the island of Vaca Key at the midpoint of the Keys island chain. It boasts many historical sites, a championship golf course and beautiful sightseeing. Rent the right type of holiday lodgings you need right on budget directly from owners of vacation rentals, chalet rentals, condo rentals, cabins or cottage accommodations in Marathon, Florida.

This American town stretches along a 10 mile long strand of beach encompassing people from every walk of life. Vacation rentals sit ocean front with miles of endless views. Learn about the town’s fishing history and enjoy the low key and relaxed atmosphere shared everywhere.

Take part in one of the numerous family friendly seafood festivals that celebrate the seafaring tradition of Marathon. Find perfect vacation rentals or condo rentals to fit your needs through Owner Direct. This area is locally referred to as the ‘heart of the keys’ due to its geographical location. Vacation with great accommodations in Marathon and enjoy activities from sailing to scuba diving in the natural beauty. Let the children play on Sombrero Beach with a living coral barrier reef.

Crane Point is a easy hike through a tropical hardwood grove which delights the young and the old. Visit the Pigeon Key island and learn a little about this history of the Keys.
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3 Vacation Rentals

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  • Marlin Bay Resort & Marina

    Marathon: Vacation Rental
    3 BDR • 3.5 BA • Sleeps 8 • #242078
    749 to 1,049 USD/night
    Newly remodeled home in The Florida Keys with 3 bedrooms and 3.5 bathrooms. Located within a private yacht club with boat slips available for rent as well a centrally located clubhouse and pool area complete with top-notch amenities.. Marlin Bay Yacht Club is a newly remodeled private community located within Marathon, Florida in the heart of The Florida Keys. As you drive through the elegant gates of the property you are welcomed by an exquisitely decorated 2-story clubhouse. As you enter the clubhouse you are greeted by our accommodating concierge team who is more than eager to assist you in planning a trip of a lifetime. The clubhouse features numerous amenities for you to enjoy during your stay, including a full-service bar, a state-of-the-art fitness center, a yoga studio, sauna, steam room, billiards, shuffleboard, multiple big screen TVs, and beautifully appointed lounges for you to relax and spend time with your family and friends. As you walk through the clubhouse and step outside you are immediately taken back by the incredible views that The Keys have to offer. Here you will find a lovely lagoon style pool, a relaxing whirlpool, modern lounge furniture to enjoy the warmth, and a full-service tiki bar. Beyond this remarkable resort-like atmosphere we also feature a private 99-slip marina complete with an experienced dockmaster to prepare you and your vessel for an amazing sea excursion. Even if you do not plan to boat during your time with us, the clubhouse, the pool area and the dramatic 3-story residences are certainly designed to please all guests and provide you with luxury accommodations. Our 3-bedroom homes are fully furnished, professionally decorated, and feature an open floorplan. As you enter the ground floor from your 2-car garage you will find a lovely master bedroom complete with its own full bathroom and private patio. As you ascend onto the second floor you will find a state-of the-art gourmet kitchen which seamlessly flows into modern dining and living areas. On this level you will also find another private deck overlooking the beautifully landscaped pool area and a conveniently placed half bathroom. Last but not least, as you arrive on the third floor you will discover an additional master bedroom complete with its own full bathroom, wet bar, and private balcony. The third bedroom is also located on this level with 2 twin beds and a private bathroom as well. If the multiple levels concern you, there is no need to worry as our homes include elevators so you can easily access each floor.
  • Bayside 3BR/3BA w/ Heated

    Marathon: Vacation Rental
    3 BDR • 3 BA • Sleeps 8 • #238859
    283 to 424 USD/night
    Soak in water views on the sun-kissed rooftop terrace of this 3BR/3BA home. Enjoy a master suite oasis with luxurious jetted tub and private deck. Keep your boat at your fingertips with plenty of dock space for rent nearby. Sleeps 8.. Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. Dock your boat nearby at one of the many spots available for rent, and then stroll back to the house to rest and recharge. You’ll feel on top of the world as you gaze over the clear waters of Florida Bay from the comfort of your 700-square-foot rooftop terrace, furnished with plenty of comfortable chairs, sofas, and recliners. End your day in the tranquil master suite. After a glass of wine or a nightcap on your private balcony, enjoy a soak in the jetted tub or a movie on the flat screen TV. ABOUT THE HOUSE For the ultimate movie night, gather your group in the spacious living area on the second floor and play your favorite films on the 55” flat screen TV. A sofa and love seat offer seating for five. Discerning chefs will appreciate the kitchen’s stainless steel GE appliances and dishwasher. Enjoy meals at the dining table for six or on the balcony with views of the neighborhood. Unwind in the first-floor master suite with a queen bed, walk-in closet, and 40” TV. The en-suite bath will be your oasis; rinse off in the walk-in shower or soak in the jetted tub. The private deck with a bistro set is perfect for enjoying coffee or a romantic cocktail for two. The second bedroom, located on the first floor, includes two twin beds, a 26” flat screen, and an en-suite bath. On the second level, the versatile third bedroom contains a queen bed and a queen-size futon to use as seating or sleeping accommodations for two. On the second-floor balcony, you’ll find a spiral staircase leading to your expansive private roof terrace. Lounge on recliners and soak in the sun, or gather your group in the shaded seating area to enjoy games, conversation, and panoramic bay views. Plan a barbecue on the shaded patio beneath the house, equipped with a gas grill and a dining area for eight. Two parking spaces are available, and you’ll find a washer/dryer on the first floor. THE LOCATION Take advantage of well-kept shared amenities. Lounge by the pool and enjoy sweeping bay views while you swim, or head down to the docks, where boat owners can rent bayside space to store their vessel. Idyllic Sunset Park Beach is just a 5-minute drive from your door. Florida Keys Aquarium Encounters, less than a half mile away, is perfect for a family-friendly afternoon of snorkeling and discovering marine life.
  • Waterfront 2BR w/ Huge

    Marathon: Vacation Rental
    2 BDR • 2 BA • Sleeps 8 • #243237
    274 to 431 USD/night
    Enjoy access to the gulf and ocean, dock your boat along the seawall, and watch dreamy sunsets from a large sunroom. Walk minutes to dining. Sleeps 10.. Enjoy expansive views of Boot Key Harbor at this waterfront 2BR/2BA (plus loft) duplex in Marathon, with easy access to the ocean and gulf. After a day on the water, dock your boat along the 45-foot seawall. Then gather to watch gorgeous sunsets from a large sunroom overlooking the water. The home offers a great walkable location, with restaurants and entertainment just a few minutes away from your door. Head across the street to Florida Keys Country Club (open to the public) and enjoy the beautiful 18-hole golf course and tennis courts. Or grab bikes and cycle around the course’s winding trail. Beautifully furnished throughout, this contemporary duplex accommodates up to ten guests between two bedrooms and a spacious lofted sleeping area. ABOUT THE HOUSE The sunny and inviting living room beckons you home after a day at the coast. A leather couch and two armchairs sit beneath tall vaulted ceilings, and there’s a 50" flat screen HDTV for group movie nights. A beautiful sunroom boasts gorgeous views across Boot Key Harbor. Enjoy morning coffee in the love seat while gazing across the water. Later, gather for lazy lunches at the dining table with seating for four. A contemporary kitchen gleams with black granite countertops and stainless steel appliances. There’s plenty of room to stash groceries and snacks in a roomy side-by-side refrigerator. A two-person dining table in the kitchen offers a casual spot for breakfast. This rental sleeps up to ten guests in the two bedrooms and loft bedroom (doesn’t have a door). Ocean greens and blues create a serene ambience in the master bedroom — featuring a king bed, double door closet, and a 32” wall-mounted HDTV. Freshen up in an en-suite bathroom with a dual vanity and tub/shower combination. Guests in the second bedroom can rest in comfort in a queen bed. Find sleeping space for six in the expansive loft area, featuring two full-size beds, a queen sleeper sofa, and a sitting area with a glass-top table and chairs. In addition, the house has a guest bathroom with a stylish tile walk-in shower, complimentary Wi-Fi, cable TV, and a washer/dryer. The driveway offers parking space for two vehicles. THE LOCATION With a beautiful waterfront setting on Boot Key Harbor, you might be tempted to kick back at home for the duration of your stay. But tear yourself away, and you’ll find Marathon has countless attractions to fill your days. Drive 8 minutes to the palm tree-dotted shores of Sombrero Beach — one of the most stunning beaches in the Florida Keys. Golf lovers can stroll across the street from home for a round on the 18-hole public course at Florida Keys Country Club. Bringing the kids. Drive 7 minutes to Florida Keys Aquarium Encounters. Or head the same distance to hike amid the mangroves and forest of Florida Keys Wildlife and Environmental Area. Restaurants, bars and shops are within a 15-20 minute walk, while the majority of dining options are a 5-minute drive away. Sample tasty Keys specialties (Including alligator tail) at The Stuffed Pig, or indulge in fabulous local seafood fresh off the boat at Barracuda Grill. Upon arrival, easily access your unit with a keyless secure door code; no need for an in-person key exchange. Your rental will be professionally cleaned and ready for you to enjoy. You can expect all comforts of a fine hotel, including shampoo, soaps, paper products, and linens. Your home will include a HomeDroid tablet (electronic guest directory) providing specific home details, local suggestions, Wi-Fi access, TV instructions, and more. If you need anything at all before, during, or after your stay, our 24/7 local team is always ready to help!
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  • On the Ocean in Key West

    Key West: 1800 Atlantic: Condo
    2 BDR • 2 BA • Sleeps 5 • #69125
    245 to 405 USD/night
    1350sq. ft. of fabulous living space located in a ocean front condo on the 2nd floor. Garden and partial ocean view from a 38ft private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year. The property is decorated and managed / maintained by me personally assuring you of a memorable vacation in a property that is way above the average investor owned rentals offered by management companies. The average temperature is 77.8 degrees, making Key West the warmest city (average temperature) in the United States. It has never been below 41 or above 98 degrees.
  • Islamorada Luxury Condo

    Islamorada: Bay Harbour: Condo in a gated community
    2 BDR • 3 BA • Sleeps 6 • #209708
    257 to 343 USD/night
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, tennis courts, gas barbeque grills, tennis equipment, beach chairs and coolers. This spectacular condo offers two master bedrooms with private full bathrooms, additional half bath and full size washer and dryer. Additionally, each bedroom and the living room has flat screen televisions with cable tv. A dvd player is included in the living room. There is free wifi and telephone included for your use. The kitchen has stainless steel appliances, granite countertops and everything you need to prepare and serve a gourmet meal. The large balcony overlooking the water offers plenty of seating. Enjoy a meal or coffee while you take in the expansive views or enjoy the sunrise. Additionally, you will have a direct view of your boat parked in a private boat slip just steps away. Located at mile marker 75, this boater’s paradise is just minutes from fishing in the gulf or ocean, diving or snorkeling beautiful reefs, jet skiing, parasailing, kiteboarding or kayaking. Call to book your vacation of a lifetime.
  • Buttonwood Bay Condo

    Key Largo: Condo
    3 BDR • 2 BA • Sleeps 4 • #256212
    171 to 186 USD/night  
    Beautiful bright and remodeled Buttonwood Bay Condo. It's one of the few 3 bedroom with 2 full bath units for rent in the community. No stairs inside the unit. It is a spacious corner unit with a 2000 sq ft single floor plan. Located close to the tennis courts and pool. Our home has new furniture and all new kitchen appliances. From the moment you enter the apartment you enjoy a beautiful view. It's the perfect place to sit back and relax. The master bedroom has a queen bed and a spacious private full size bathroom with double sinks along with a large shower. The master bedroom has his and hers walk in closets. The second bedroom has a queen size bed and plenty of closet space. The third bedroom has a trundle bed and a television. The second renovated bathroom has tub/shower and modern glass sink. The kitchen features all new appliances and is fully equipped. The dining table seats 5 and the kitchen bar seats 3. The relaxing and beautiful view of the waterway is fully visible from the living room and partly from two of the bedrooms. Enjoy sitting and relaxing on the large comfortable leather couch. The views are amazing. You can open the wall to wall glass sliding doors and bring the outside in as you feel the sea breeze. From the unit you can see manatees, tarpon or even porpoises. Enjoy the morning light as you sip your coffee or the beautiful sunsets off the Martini Deck located very close to the unit. Our home is equipped with Wi-Fi. The coral rock boat dock is adjacent to the building and a few steps to the Florida bay. In addition to the very rare sandy beach, the community of Buttonwood Bay has: - 3 heated pools - 5 tennis courts - a renovated clubhouse - a basketball hoop - a volleyball court - a game room - a library - a newer fitness center overlooking the marina - saunas - an observation deck - several sunset decks throughout the bay - Boat launch - large boat slips that may rented Buttonwood Bay has a 24 hr manned gate-house and security patrol throughout the private 42 acre community. There are many places to visit such as John Penne Kamp Coral Reef State Park, Everglades National Park, and all the other islands leading to Key West. There are many fun things to do like fishing, swimming with the dolphins and feeding the tarpon at Robbies. You'll also have excellent dining choices from casual to fine dining located nearby. We welcome you to our special home away from home and know you will love it
  • Executive Bay 2 / 1.5

    Islamorada: Executive Bay Club: Townhouse in a gated community
    2 BDR • 2 BA • Sleeps 4 • #234599
    140 to 140 USD/night
    Come to Paradise and Enjoy it with Comfort. Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your own Dock and incredible sunsets. Our Two Story Unit is nicely decorated and furnished, Granite Kitchen counter tops, stainless steel appliances , complete with everything you need. Large Living Room and Dining Room with large flat panel LCD TV , and Outside Patio with a relaxing atmosphere. Master Bedroom (Queen Size Bed) plus a Loft, Second Bedroom Has 2 Twin Size Beds, Full Bathroom upstairs, Half Bathroom on the first floor. This unit is in a great location, across the pool, clubhouse and steps to the beach and fishing pier.

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