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From sunrise to sunset you can enjoy the many activities our Florida Keys resort has to offer. Fine restaurants and shopping are just minutes away, along with boating, fishing, snorkeling, diving, Everglades eco-tours, glass bottom boat reef trips, para-sailing, wave runners, and swimming with the dolphins....
Featured review
The incredible view! The kitchen has everything (though we didn't intend to do a lot of cooking!). The unit has a short walk to the pool, snackbar/bar, and the restaurant/bar. There is also a small natural...
Distance to beach: 0.3 miles to Exclusive Inch Beach
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Note!! ALL Reservations are accepted on a "Saturday to Saturday" check in/Check out basis. VACATION HOME IS LOCATED IN KEY COLONY BEACH just a 3-4 Minute Walk to the Private Members Only "CABANA BEACH CLUB" where you receive a Pass.Welcome to our Casa Mar Azul III, an upscale...
Featured review
This house is exactly as pictured. This was our second visit to this home and we will be back. Pool was clean and a nice plus. Location is a nice quiet neighborhood
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Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, giant connect four, ping pong and more! Perfectly situated on the water with stunning views, sunrise and...
Featured review
The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!
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MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 30' boat), fish cleaning station, private pool, hot tub, and...
Featured review
Meredith and Pineapple Properties were very accommodating, and answered all of our questions. The home, the pool, and the hot tub are all in great working shape, well-maintained, and clean. The property...
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Family House in Big Pine Key, Fl on the water. Bring your Boat and have easy access to the most beautiful waters of the Keys. Boat dock on the back of the house, and house comes with everything, it will make you feel at home.Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront...
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Distance to beach: 8 miles to Sombrero Beach
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Welcome to Marlin House – your perfect Keys getaway! This 2-bedroom, 2-bath coastal retreat offers the perfect balance of comfort and adventure. Relax in your own private plunge pool, enjoy fully stocked amenities for a stress-free stay, and make yourself at home with thoughtful touches throughout.Step...
Featured review
We had the most wonderful stay at Marlin House on Duck Key . Thank you Paola ! You were such an exceptional host !!!! The townhome is tastefully appointed , clean, great location, lovely patio with private...
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Special discount for stays of 2 weeks or more!There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries that you will love! The home is just 3 years old and WELL apportioned...
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Watch dolphins play in Shelter Cove while swimming in our oversized poolRelax in the private pool with the Spectacular Shelter Bay in the background...Our home is located directly on Shelter Bay in Key Colony Beach with some of the most spectacular views of open water a guest can ask for. We have...
Featured review
We enjoyed are stay at this well appointed and conveniently located vacation home. The setting is perfect and the home was loaded with every convenience you would need. Margie, the property owner, is...
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Sun Kissed Tails is a beautiful 3 bedroom 3 bath townhome, with a modern coastal feel, in the Hawks Cay resort on Duck Key, MM61.ENJOY THE POOL AND BEACH AT THE OCEAN FRONT CABANA CLUB, just a 15 min drive to Key Colony Beach. The Cabana Club has an olympic size pool, Tiki Bar and restaurant, ocean...
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Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside...
Featured review
We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage...
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Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings....
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Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the...
Featured review
Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the...
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The Blue Manatee (formerly Sunshade Villa), located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool and all the amenities you can imagine...
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2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping,...
Featured review
The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used...
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Welcome to your perfect tropical getaway! This stunning, completely remodeled half duplex in Key Colony Beach offers a blend of modern luxury and coastal charm. From top to bottom, no detail has been overlooked in creating this immaculate vacation retreat.Relax and unwind in the spacious living areas...
Distance to beach: 2 miles to Founders Park
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This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios...
Featured review
This was the nicest home overall I have rented. If you have a boat, don't look elsewhere. Everything in the house functioned and the house had everything one would need, even for people who do cook while...
Distance to beach: 900 yards to Sombrero Beach
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"BELLA VISTA" - a Spectacular Oceanfront home in Marathon, Fla. with an Invisible-edge heated salt water pool that overlooks the Atlantic Ocean. Open Water Unobstructed VIEWS. VERY PRIVATE. Newly renovated! This 4 bedroom/3.5 bath home can comfortably sleep 8 people. Three bedrooms have King...
Featured review
Don’t think twice about booking this slice of heaven. My family of seven stayed at this glorious home. Absolutely spotless and very well stocked with everything you need. The views are amazing!! 5...
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We would like to invite you to stay at our peaceful keys getaway. Enjoy the spacious porch overlooking the pool and canal, this is great for my wife and I to watch our kids while they are swimming and fishing off the sea wall. As you can tell by the pictures you can catch hugh snapper right off the sea...
Distance to beach: 1 miles to Sombrero Beach
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Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9:00 AM. Check in directions are emailed to you the week prior to your arrival { please check "spam" } Pups...
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Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2...
Featured review
The condo was neat and well furnished. Great location and a beautiful property! Founders park across Rt 1 is a great take with a nice beach and very helpful staff at the visitors center.
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Come have your first sunset drinks compliments on us at Island Fish Company. $100 Gift Certificate to Island Fish Company Included. No Expense Spared! New Construction Bayfront Home With Private Dock and Pool.5 O'Clock Somewhere Bay House is a piece of paradise on the Vaca Cut waterway in Marathon....
Featured review
This vacation getaway home had everything we needed plus Lauri was an extremely responsive host. The location was excellent. We could walk to the Aquarium that was across the canal or drive ten minutes...
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This Condo comes with tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.
Featured review
Spacious 2 bedroom condo with everything you need. Beautiful view, well equipped kitchen. Comfortable furniture. Well maintained grounds and great pool. You're able to buy fresh lobster/ seafood right off...
Distance to beach: 1 miles to Sombrero Beach
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Embark on an idyllic getaway to our spacious 4-bedroom, 3-bathroom vacation villa nestled in Marathon, the heart of the Florida Keys. Escape to Stay Anchored, where tranquility meets luxury. Boasting a prime location on a spacious canal, our retreat features a private heated and chilled pool, inviting...
Featured review
Stay anchored at Sombrero was an amazing property....The location was perfect for our group. The house is very comfortable and welcoming. The property owners are exceptional responding promptly to any...
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Oceanfront with dock and swimming pool...rare find ifor Key West..gorgeous house with 3 bedrooms 3 baths, laundry room, large open kitchen leading to wraparound deck...paddleboard, kayak, swim and snorkel in the clear friendly sea right off your property..10 min to famous Old Town and its many entertainments...
Key Amenities
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Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...
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"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally,...
Featured review
Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!
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Special discount for stays of 2 weeks or more!See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned...
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This pet-friendly home completed in 2012 has 5 rooms, 3 king-size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep the...
Featured review
SIX STARS * * * * * *This is a wonderful home with channel access right behind the house. It's perfect for the whole family, very spacious. The owners are very accommodating, making sure everything...
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Gulf side Gem, 45 ft. Dock, pool , hot tub and moreSpacious 3 Bedrooms and 3 Baths 1,600 sq ft home overlooking a canal with a brand new dock that spans the width of the property complete with a fish cleaning station and private pool and brand new hot tub. The Open Concept Living and Kitchen Area...
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Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional...
Featured review
I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would...
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2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants...
Featured review
This is the perfect place for a Florida vacation. It has everything we were looking for and more. Private beach, quiet location, mature trees with coconuts and bananas. Tiki hut with a wet bar and comfy...
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This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.
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Updated two bedroom, two bathroom half duplex on 11th street. Excellent location towards the end of the canal yielding instant access to Vaca Cut and the Open Atlantic, 37 ft of deepwater dockage on an extra wide canal is perfect for fisherman and families alike! Enter through the street-side screened...
Distance to beach: 6 miles to John Pennekamp State Park
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1 BR/1 Bath Rare Find! Lovely oceanfront home with large private boat basin. This ground-level house has two enclosed sleeping areas - a master bedroom with a king bed, and a private alcove providing sleeping space for up to 4, with 2 bunks and a full-sized bed (separated from the living room by an...
Featured review
A lovely property, a comfortable house with all the amenities and a covered outdoor patio right on the ocean where we spent most of our time reading, sunning, and watching the wildlife fly, swim and crawl...
Distance to beach: 100 yards to Sombrero Beach
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Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home...
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Private Beach, ocean front home with pool on Cudjoe Key.Home includes;- Master bedroom suite with 32' flat screen TV, full bathroom including tub and shower for 2, sliders open to private Master Suite deck with ocean view and private beach.- 2 additional bedrooms with Jack-n-Jill bath-...
Featured review
We really enjoyed the large house. The easy to launch kayak area was very convientant. Location was great - 25 minutes to Key West. The sunsets were breathtaking. House was well equipped with every you...
About this property
The Main House is a fully furnished, two-bedroom, two-floor house facing the bay that can sleep up to two adults and six children.On the second floor, the master bedroom is at the top of the stairs and contains two queen-size beds, a large closet, and access to the full-size bathroom, which is also...
Distance to beach: 100 feet to our back yard...steps away from the house
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The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerland Key, mile marker 25. The house is an open floor plan with panoramic Atlantic Ocean views and a large wrap-around deck. Two bedrooms (the oceanside bedroom has a king bed and the...
Featured review
Fantastic location, the view from the sunroom is fantastic. Postcard sunrises to start the day! House was very well equipted with everything we needed during our stay, hosts reached out to check on us...
Distance to beach: 3 miles to Founders Park
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Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...
Distance to beach: 0.1 miles to Sombrero Beach
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Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!!(We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.)Our houses are safe and clean because we disinfect them with the highest...
Featured review
The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing....
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Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying...
Featured review
Thank you for you help in researching a vacation rental . We love key west an we will be inquiring with you in the future
Distance to beach: 2 miles to Picnic Island (by Boat)
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Beautifully kept private and secure canal front (220' of waterfront) home. Located at the end of a dead end street in a residential neighborhood alLows for privacy and extra relaxation. Fully updated kitchen, fully equipped with coffee maker, espresso maker, blender, bullet blender, etc. Ideally...
Featured review
The property is updated, super comfortable, spacious, and beautifully decorated. We will be visiting again!
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"Wow beyond wow! This place had everything we needed and more. We like to rent a house where we can spend most of our time there enjoying family time. The pool and all the games with the game room and infinity table and the dining turned ping pong was amazing. Eric was very responsive..." -...
Featured review
Eric was the perfect host. We escaped a cold and snowy winter for Marathon and this home offered us the perfect get away! It included everything we could have needed…games, pool, grill, plenty of space...
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Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada...
Featured review
A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us....
Distance to beach: 2 miles to Smathers Beach
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**Peaceful Paradise in Key West Golf Club – Monthly Stays Welcome**Escape to serenity in this beautifully appointed 2-bedroom townhouse nestled within the gated Key West Golf Club community. Designed for monthly stays of 29 days or more, this home offers the perfect blend of comfort, convenience,...
Featured review
The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific...
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Villa Sombrero – Private Waterfront Living with Sunset Views in the Florida KeysVilla Sombrero is a peaceful waterfront retreat overlooking Boot Key Harbor, offering breathtaking sunsets to the west and refreshing island breezes flowing in from the east through Sisters Creek. A natural waterway...
Featured review
We really enjoyed the house, very well appointed! 5 kayaks for you to use anytime , and believe me we used them and had a blast! Debra the owner is a dream even had a Bottlle of Champaign and a cake waiting...
Distance to beach: 40 feet to Across the street
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FAMILY FRIENDLY GORGEOUS HOME WITH DIRECT WATER VIEW OF LARGO SOUND! WATCH THE SUN RISE FROM THE COMFORT OF YOUR LIVING ROOM! 3 BEDROOMS 2 BATHROOMS BEACH AND BOAT LAUNCH INCLUDED IN RATE! THIS IS THE OPPORTUNITY OF A LIFETIME! KING SIZE BED IN MASTER BEDROOM, Queen bed in 2ND BEDROOM AND TWIN...
Featured review
This place is amazing, beautiful beach right out the front door is why we come here. The host is the best, Nancy catered to all our needs. The home is nicely decorated, it had everything we needed. We will...
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Canal front, Dock, Hot Tub and Cabana Club AccessWelcome to Orchid House, a lushly landscaped canal front home located on the beautiful island of Key Colony Beach. This property comes with boat dockage , private hot tub and access to the Cabana Club pool and beach.When you first drive up to the...
Distance to beach: 3 miles to Sombrero
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Plan your Marathon Trip - Stay at Manatee Cove-4BR/2BA vacation home. Pool with Spa, Tiki, Quick Atlantic access!Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on the Atlantic side of the canal in Marathon. Our home offers the best pool in our area; who can say no to a hot tub, pool, and bar stools...
Featured review
My family and I had a wonderful week here. The owner and property manager were both a pleasure to work with. Our favorite amenity was the pool and hot tub. We had plenty of space and all of the beds were...
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DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you...
Featured review
We had a fabulous stay in your property. We really appreciated all of your amenities. We love to cook some of our meals in and you had a great selection of pots and pans and dinnerware. We also like...
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