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 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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4 Vacation Rentals

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  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241323
    $251 to $601 USD/night  
    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and hotel-quality towels and linens. And we make it easy to stay with us. Drive straight to your rental and access the rental with a unique lock code that we give only to you. When you book, we will send you our mobile app with directions, lock code, and instructions. We’re available 24 hours a day with live help. All vacation rentals follow local and state tax rules. Each reservation includes applicable taxes, a cleaning fee, and a Property Damage Protection policy.
  • All Photos, Amenities, Calendar,

    All Photos, Amenities

    Marathon: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #241322
    $251 to $601 USD/night  
    All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper products and hotel-quality towels and linens. And we make it easy to stay with us. Drive straight to your rental and access the rental with a unique lock code that we give only to you. When you book, we will send you our mobile app with directions, lock code, and instructions. We’re available 24 hours a day with live help. All vacation rentals follow local and state tax rules. Each reservation includes applicable taxes, a cleaning fee, and a Property Damage Protection policy.
  • Perched on the Largest

    Perched on the Largest

    Marathon: Vacation Rental
    • 4 BDR
    • 3 BA
    • Sleeps 10
    • #240137
    $320 to $632 USD/night  
    Perched on the largest deep water canal in the Florida Keys, this fresh 4BR/3BA home offers a large boat dock, a glittering pool, and both a fish cleaning station and a dedicated freezer. Newly updated with ceramic tile floors and mermaid décor. Sleeps 8.. Relish in emerald canal views at this lovely 4BR/3BA Key Colony Beach home, complete with a spacious waterside deck and sparkling private pool. New wood-grain ceramic tiles line every room, with fun mermaid accents greeting you at every turn. Bring your boat along or rent one nearby to make use of your large, private dock. Anglers will appreciate the fish cleaning station and dedicated freezer. ABOUT THE HOUSE New ceramic tile lines the floors of your freshly updated home, with playful mermaid décor lighting up each room. The open-concept living room boasts a massive sectional couch and a recliner for movie nights and TV marathons on the 55” flat screen TV. White appliances and cabinetry gleam in the kitchen, where expansive granite counters make meal prep a breeze. Find all the gadgetry and cookware you could dream of to fix simple beach picnics or elaborate dinners. Six can sit down to breakfast at the sweeping breakfast bar, with room for eight in the elegant formal dining area. Step out to the patio to find outdoor dining, sun loungers, and a full outdoor living room set. Slip into the pool for a relaxing swim among emerald canal views. Make use of the barbeque grill, along with your large private dock and a dedicated fish cleaning station. There’s also a standalone freezer for storing your catch inside. The king-size master bedroom offers a 42” TV and a pristine en-suite bath with a double-sink vanity and a tiled walk-in shower. The second and third bedrooms both have cozy queen-size beds and a shared en-suite bath with a walk-in shower, and the fourth has two twin-size beds. Another full guest bath is equipped with a tub/shower combination. Extras at the house include driveway parking with room enough for a small RV, a washer/dryer, and complimentary Wi-Fi. THE LOCATION Your Florida Keys home has it all — a private dock on the canal and South Beach's sand, sun, and surf within half-mile from your door. Rent a rig at Miami Five Star in 7 blocks, and dine on everything from pizza to tacos Mediterranean steps away.
  • Soak in Water Views

    Soak in Water Views

    Marathon: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #238859
    $179 to $393 USD/night Credit Card
    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.
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  • Islamorada Luxury Condo with 50' Private Boat Slip

    Islamorada Luxury Condo

    Islamorada: Bay Harbour: Condo in a gated community
    • 2 BDR
    • 3 BA
    • Sleeps 6
    • #209708
    $243 to $343 USD/night Paypal
    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.
  • Executive Bay 2 / 1.5 - Great Location. Great Unit!

    Executive Bay 2 / 1.5

    Islamorada: Executive Bay Club: Townhouse in a gated community
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #234599
    $164 to $171 USD/night Paypal Star Rating
    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, 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.
  • On the Ocean in Key West

    On the Ocean in Key West

    Key West: 1800 Atlantic: Condo
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #69125
    $245 to $405 USD/night Credit Card
    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.
  • Moon Bay Yacht and Tennis Club

    Moon Bay Yacht and Tennis

    Key Largo: Moon Bay Yacht and Tennis Club: Condo in a complex
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #13373
    $128 to $228 USD/night Credit Card
    This beautiful condo is on the fourth floor. There is an elevator in the building. Being on the fourth floor makes for a spectacular view from the screened in porch, living room, dining room, and master bedroom. Ceiling fans. Moon Bay has everything you need for a great vacation. There are free tennis courts, pool, saunas, a private boat slip,basketball hoop, and a dock for fishing and swimming to mention just a few of the amenities. There is a recreation room with ping pong and a water front grill. Wireless Internet.
  • Located in Old Town

    Located in Old Town

    Key West: Vacation Rental
    • 1 BDR
    • 1 BA
    • Sleeps 3
    • #238465
    $88 to $146 USD/night Credit Card
    Located in Old Town, this restored 1920s conch house apartment is classic Key West. Near Duval Street, beaches, and the historic seaport. Just a short walk to dining and shopping. Enjoy access to a heated pool. Sleeps 3.. Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This light-filled, open-concept apartment has vaulted ceilings and inviting relaxation spaces. Enjoy a movie in the comfy living room, with a queen-size sleeper sofa and 37” flat screen TV. Cook your meals in the well-equipped kitchen, with a convenient island with seating for two. The bright dining space accommodates four. Take a dip in the shared heated pool, or sit out on a private porch and enjoy the cool shade provided by the surrounding palm trees. A bubbling fountain in the front yard welcomes you to the property. The bedroom has a plush queen-size bed and a full bath. Amenities include a washer/dryer. And there is open street parking available for one vehicle. THE LOCATION A plethora of local attractions are nearby. Southernmost Point and the Ernest Hemingway museum are both an 8-minute drive from the house, while famed Duval Street is less than a mile away. There are plenty of walkable restaurants, shops, and attractions on Fleming Street, so you never have to go far to have a great time.
  • Across the Bay from

    Across the Bay from

    Islamorada: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #241141
    $390 to $586 USD/night  
    Across the bay from the Everglades National Park, this 3BR/2BA waterfront home features a private beach, dock, kayak, and paddleboards. You’ll also love being near John Pennekamp Underwater State Park for premier diving. Sleeps 8.. Situated on the beautiful Florida Bay, this 3BR/2BA Islamorada home offers an idyllic waterfront haven with its own private beach, dock, kayak, paddleboards, and sprawling backyard with a volleyball net. Spend leisurely afternoons fishing off the dock before cooking up your catch on the grill. Enjoy your meal at the six-person patio table, then relax in one of two sun loungers. Or enjoy spectacular sunsets from the waterside hammock. Conveniently located, this home sits across the bay from the entrance to Everglades National Park. Nestled between Snake and Tavernier Creek, you’ll also be close to premier snorkeling and diving at Pennekamp Underwater State Park -- just 15 miles away. ABOUT THE HOUSE This home features a welcoming open floor plan with cool, tiled flooring and an abundance of natural light. After a day of fishing or diving, kick back in the main living area with a couch, love seat, and oversized chair. Enjoy your favorite shows on the 65” flat screen HDTV. Find more space to unwind in the adjacent sunroom, furnished with a couch, love seat, and two inviting armchairs. Play a board game or a round of cards at the four-person glass top table. It’s easy to whip up meals in the spacious kitchen, equipped with high-end appliances. A three-person kitchen bar offers a casual spot to chat while the chef preps dinner. In the dining area, there’s room for six to enjoy meals amid spectacular sunset views across the bay. With sleeping space for up to eight, this house features three bedrooms, each equipped with an AIR CONDITIONING unit to ensure a good night’s sleep. The master bedroom includes a stately king-size bed and a large closet. Across the hall, another king bed awaits in the second bedroom, which also has a large closet and a convenient office nook. Guests in these rooms share a bathroom with a walk-in shower. In the third bedroom, you’ll find two twin-over-full bunk beds and a Jack-and-Jill bathroom (shared with the sunroom) with a walk-in shower. Outside, the tropical backyard provides a direct view of the Florida Bay as well as its own private beach. This outdoor retreat has it all: a full-size sand volleyball court, outdoor dining, a charcoal grill, a fire pit, and a private dock with outdoor seating. Additional guest amenities include complimentary Wi-Fi, cable TV, a washer/dryer, and parking for four cars in the driveway. All leases require a minimum 31-day term. THE LOCATION Within a 30-minute drive, John Pennekamp Coral Reef State Park offers some of the best diving in the U.S. Along with superb snorkeling, sailing, and glass-bottom boat tours. Spend the day exploring the park’s 70 nautical square miles of Atlantic Ocean waters, or head across the bay to enter the Everglades National Park for wildlife sightings and thrilling swamp tours. For more outdoor adventures, swim with dolphins at Theater of the Sea (an 8-minute drive), and hit the hiking trails in Windley Key Fossil Reef Geological State Park (6 minutes). When dining out, head to Marker 88 for a laid-back beachfront grill specializing in seafood and cocktails. Or go for craft beers and hamburgers at MEAT Eatery & Tap Room. Both are within a 7-minute walk.
  • Kick off your Sandals

    Kick off your Sandals

    Islamorada: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #238432
    $143 to $205 USD/night Credit Card Pet Friendly
    Kick off your sandals and get into full vacation mode—this 2BR/2BA Islamorada house is the ideal home base for your relaxing getaway. Enjoy a quiet private beach. Walk to restaurants and bars. Sleeps 6.. Straight from the pages of a travel magazine, this 2BR/2BA Islamorada house commands a prime location overlooking the jewel-toned waters and white sands. Inside, bright sunshine comes in through multiple sliding glass doors, bathing the open spaces in natural light. Start and end your day out on the screened balcony. When it’s time for a night out, you’re just a short walk from great restaurants and bars. The heart of Islamorada is just 8 miles away. The area is also known for outstanding snorkeling and scuba diving. ABOUT THE HOUSE Take in the panoramic views from the screened balcony that spans the front of the house. Curl up with a book on the patio couch, and dine al fresco at the four-person table, enjoying warm breezes and the sound of the waves. Tasteful beach decor and neutral colors create an inviting ambiance in the living room. Settle into the couch to watch the 39” flat screen TV, or just kick back and enjoy beautiful ocean views through the sliding glass doors. Pack lunches for the beach and make inspired dinners in the well-equipped kitchen. Sit down to meals around the dining table for four. Two bedrooms sleep six comfortably. Slumber in the master bedroom’s king bed, and enjoy plenty of storage in the walk-in closet and several dressers. Take in the water views through the sliding glass doors. An en-suite bathroom offers a tub/shower combination. Guests will love the views from the second bedroom, featuring two full beds, a large closet, and sliding glass doors out to the balcony. The en-suite bathroom has a tub and shower combination. There’s parking underneath the home for one car with additional two spots in the driveway. Other amenities include an outdoor shower and a laundry room with washer/dryer. THE LOCATION Known as the “Village of Islands,” Islamorada (8 miles away) is brimming with natural beauty and lots to see and do. Get up close and personal with dolphins at the Theater of the Sea, browse the exhibits at the History of Diving Museum, and explore the Windley Key Fossil Reef Geological State Park. The area offers exceptional scuba diving and snorkeling, which you can do on your own or hire a professional guide for a tour. The Caloosa Cove Resort is a 15-minute walk away and has a full-service marina and island store. Treat yourself to dinner out at one of the nearby restaurants. Local favorites include Habanos, which offers oceanfront dining, and the Safari Lounge for an after-dinner nightcap.
  • This 2br/2ba with Canal

    This 2br/2ba with Canal

    Key Largo: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 8
    • #238387
    $185 to $217 USD/night Credit Card
    This 2BR/2BA with canal access has a private dock for boats up to 35’. Savor a cocktail in the shade of the backyard tiki hut, and soak in the hot tub while watching a movie on one of two flat screen TVs. Bonus bedroom in the finished garage.. Make the most of the Key Largo sunshine in the home’s outdoor oasis. You’ll feel cool and comfortable on the warmest summer days with a misting system that provides invigorating refreshment and controls mosquitos. Relax with friends under the shaded tiki hut or unwind with a soak in the hot tub. Mixologists, try your hand at new cocktails in the beach-themed outdoor bar. With two flat screen TVs, you can watch films from the hot tub or the bar. A private dock with access to the Gulf accommodates boats up to 35’. A high-tech boat lift with remote control makes raising, lowering, and storing your boat a breeze. ABOUT THE HOUSE The second-floor living room, kitchen, and dining area are bright and comfortable. The living room has a leather sectional with seating for four, a perfect spot to put your feet up and catch a movie on the 51” TV. Just outside your door, a private outdoor oasis awaits. Beach-lovers will adore the tiki hut, with a sitting area, hot tub, and two flat screen TVs. Barbecue on the propane grill and dine at the outdoor dining table, then cap your evening with a refreshing cocktail prepared at the outdoor bar. Or make meals in the well-equipped kitchen to enjoy at the dining area for four. After dinner, step out onto the balcony to enjoy views of beautiful Key Largo. The second-floor master bedroom is a welcoming retreat with a queen bed, walk-in closet, and 41” TV. A bathroom with walk-in shower is conveniently located adjacent. On the first floor, the guest bedroom sleeps three with a twin-over-full bunk bed. An en-suite bathroom and 31” TV make this a private hideaway perfect for kids. For larger groups, a bonus bedroom in the finished garage sleeps an extra three guests on a twin inflatable mattress and full-size Murphy bed. Amenities include a washer/dryer in the garage. There is ample driveway parking for four cars. For fishing enthusiasts, a freezer in the garage keeps your catch fresh. THE LOCATION This Key Largo home is perfect for sailors, equipped with a dock for boats up to 35’ and a remote-controlled boat lift. The open waters of the Gulf of Mexico are a short sail away. View underwater sights while snorkeling at John Pennekamp Coral Reef State Park, less than a 10-minute drive from your door. Paddle or kayak through the Everglades for a true Key Largo experience.
  • 14 Night Minimum Stay

    14 Night Minimum Stay

    Key Colony Beach: Vacation Rental
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #226391
    $171 to $200 USD/night Credit Card
    14 NIGHT MINIMUM STAY. 14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/airconditioning and a private patio or balcony. This unit has a great corner view of the ocean. The kitchen is equipped with stove, refrigerator, dishwasher, utensils, cookware, glass selection and dishes.Linens and towels are also supplied. Cable TV is provided in each unit and on-site Internet wireless access is available at no additional charge. All of the condos are decorated according to the taste of the individual owners 14 night minimum stay per condominium association rules. 14 NIGHT MINIMUM STAY.
  • Located around the Corner

    Located around the Corner

    Key West: Vacation Rental
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #239593
    $293 to $720 USD/night  
    Located around the corner from Key West’s bustling Petronia Street and Restaurant Row, this 3BR/3BA home boasts a chef’s kitchen with upscale appliances and granite countertops, as well as a private heated pool and tropical deck. Sleeps 6.. Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Step out to your backyard for a dip in the private pool, set amid lush landscaping, and enjoy meals at the outdoor dining table for four. Located three blocks from Duval Street, and just around the corner from lively Petronia Street and Restaurant Row, you’ll find everything from Caribbean eats to crepes to kosher fare, mere steps from your door. You’re also near an array of eclectic independently-run boutiques. ABOUT THE HOUSE Step through the sliding glass doors off the living room to swim in the crystal-clear heated pool with a unique waterfall feature. Linger over al fresco meals among lush tropical gardens. The open-concept living area seats five between a plush sofa and chair; enjoy a 46” flat screen Apple TV and Sonos theater system. The chef’s kitchen makes cooking a pleasure with its granite countertops and stainless-steel appliances that include an oven with warming drawer, and a Thermador four-burner stove with griddle and grill. Enjoy coffee at the kitchen island with seating for three, or dine at the four-person table. When it’s time to turn if for the night, you’ll find a bedroom with two twin beds and a 37” flat screen TV just off of the entryway. A bathroom with a walk-in glass shower sits adjacent. Upstairs, the second bedroom features a queen bed, 37” flat screen TV, walk-in closet, and bathroom with walk-in shower. Down the hall, the master bedroom has a queen-size bed, 42” flat screen TV, walk-in closet, and a luxurious en-suite bathroom with double-sink vanity, large jetted tub, and a separate shower with dual showerheads. Two double doors off the master bedroom lead to a balcony. Guest amenities include complimentary Wi-Fi, Apple TV, a washer/dryer set, and parking for two cars. All leases require a minimum 31-day term. THE LOCATION Situated on a quiet lane in Bahama Village, your rental home is around the corner from many of Key West’s favored restaurants and shops. Traveling with kids. You’re a short drive from the Key West Aquarium and the Mel Fisher Maritime Museum. Have literature lovers in your midst. The Ernest Hemingway Home and Museum is blocks away. And the beach is a 5-minute drive.

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