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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 beautiful waterfront home was recently updated and features 3 bedrooms with a spacious master bedroom and 2 bathrooms. The home has a very large kitchen with an island and two refrigerators. The kitchen is fully equipped with pots, pans, utensils, plates and more. We also provide a coffee machine...
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...
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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: 2 miles to Founders Park
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Welcome to your dream getaway in Islamorada! This 3-bedroom, 2.5-bath paradise boasts a gourmet kitchen with a Viking gas stove, a spacious dining area, and Internet-ready TVs for game days or movie nights.On the first floor, you will find two bedrooms, a full bathroom and a large entertainment area...
Featured review
We had a wonderful time here. The location is perfect. Close to restaurants, shops, and attractions. We spent a lot of time floating and frolicking in the canal. The house was spotless. The kitchen was...
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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...
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...
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We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with...
Featured review
I can’t say enough about this property and the owners. From the ease of booking to our entire stay, we were more than happy. The home is top notch, great beds and very well stocked. The owners were...
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Welcome to your remodeled 2 - bedroom, 2 - bathroom vacation rental that has everything you need! The Master bedroom features a comfortable king size bed with a private bathroom that has a walk-in shower. The second bedroom has 2 twin beds and a connecting bathroom. The kitchen boasts beautiful granite...
Featured review
Our trip was wonderful! The condo was clean and nicely decorated. We had plenty of room and the view was priceless!
Distance to beach: 50 yards to Private sunning beaches at Anglers
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Book here and SAVE VRBO's $500-700 Booking fee for any stay!! PLUS our diect rates are the same or usually lower than on VRBO. Click on the "Link" to the left to see our many great reviews on our direct rental site.Welcome to Anglers Reef, a very special community of vacation homes....
Featured review
Our stay couldn't have been better. Great gated community beautifully landscaped, the house is great everything you could need. Very nice layout, Cold AC Great Pool just steps away, Location is exactly...
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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Forget your worries in this spacious and serene space. Enjoy all that Marathon has to offer in this perfect location within walking distance to Cocoplum beach. This spacious completely renovated 2 bedroom condo offers everything that you will need for your vacation rental. Offering a boat slip right outside...
Featured review
Fantastic condo in Marathon. Great location with its own community boat ramp, a dock right next to the condo, a pool, and a nice sandy beach a very short walk away. The best part was Katie Carillo the realtor...
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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...
Distance to beach: 0.1 miles to Sombrero Beach
Key Amenities
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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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Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the...
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Enjoy Beachfront Island Life from our condo right on the Atlantic Ocean. We are literally only 10-20’ from the water depending on the tide.Totally remodeled in 2022. All new kitchen with high end appliances. Beautiful master bath with large walk in shower for two.Huge wrap around...
Featured review
Clean and fully renovated with wraparound balconies overlooking the sandy beach and palm trees. Amazing sunrises and sunsets over the ocean. South and west facing windows. Great beach and communal pool....
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Waterfront 4BR/3BA duplex in Marathon, just a 2 minute walk to Sombrero Beach! Perfect for families, this home features a private heated pool, shared dock for one 30’ boat, and a fenced yard. Enjoy modern comforts, a fully stocked kitchen, and easy access to all the Florida Keys have to offer. Comfortably...
Featured review
Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.
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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...
Distance to beach: 3 miles to Sombrero Beach
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This charming oceanfront property is the perfect getaway for your next vacation. Located just steps away from the ocean, this cozy retreat features stunning views, modern amenities, and a spacious deck for outdoor relaxation. Enjoy the convenience of nearby shops, restaurants, and attractions. Book your...
Featured review
Newer, modern, comfortable, and well decorated oceanfront property. Had everything we needed and more. Beautiful views from the deck and very nice outside area. We appreciated that there were great...
Distance to beach: 0.5 miles to South Beach
Key Amenities
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This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill...
Featured review
This small unit had everything we needed. Very clean and convenient to everything we wanted to do. Will rent again! Pam was so easy to work with.
Distance to beach: 0.0 miles to Inch Beach - Just a 3 minute walk
Key Amenities
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Note!! ALL Reservations are accepted on a "Saturday to Saturday" check in/Check out basis.Casa Mar Azul II is a charming 2 Bedroom, 2 Bath 1/2 Duplex (Sleeps 2-5) located at 12 7th Street directly across from the Key Colony Beach Golf Course with a great view out back of a 200 foot canal....
Featured review
We were looking for a place in the keys to dock our boat while enjoying all the Keys has to offer. The casa was well appointed for anything you might need in the kitchen including crock pot and blender....
Distance to beach: 2 miles to Picnic Island (by Boat)
Key Amenities
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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!
Key Amenities
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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...
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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...
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Gulf-Front Modern Luxury | 5BR w/ Rooftop Deck, Infinity Pool, Dock & More! Indulge in an unparalleled luxury experience in this breathtaking 5-bedroom, 5.5-bathroom estate in Marathon, Florida. With direct Gulf views, high-end amenities, and a sleek modern design, this home is a dream getaway for...
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Welcome to our waterfront family home located in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and receive...
Featured review
The property was amazing the views of the water were fantastic. The dock area was super great for fishing off of every day. The elevator was a life savior for getting suit cases and groceries up stairs....
Distance to beach: 3 miles to Anne's Beach State Park
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This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your...
Featured review
All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every...
Distance to beach: 1 miles to cocoplum
Key Amenities
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Are you ready to Seas the Day? 30 steps to the water and heated pool, this completely renovated 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front community - steps from heated (and chilled) saltwater pool (easier on eyes, skin and...
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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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Great for Family Reuions, and Large Groups vacationing in the Florida Keys! Fabulous 6500 sq ft. vacation paradise. Includes everything you need for a perfect Family Reunion or large destination vacation.Private Vacation Rental Waterfront Home with 6 Bedroom 5 Baths Private Pool and Spa ~Tiki Hut,...
Featured review
From beginning to end it was a pleasure working with Liz to secure the week of family fun! The estate was everything that we needed it to be with plenty of room for our children and grand children. The...
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Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca...
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Tingler Retreat is a tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 2 bikes,...
Featured review
My husband and I hosted our daughter, son in law and 2 grandkids for a week. They loved the pool and the closeness to sombrero beach. It’s at nice quiet neighborhood with a lot of parking. The house is...
Distance to beach: 0.5 miles to Higg's Beach
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Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district...
Featured review
We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more....
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Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace and luxury. Ocean Residences blends modern touches with a secluded retreat atmosphere, providing the ultimate getaway experience. As our vacationer and a new addition to our family, you'll enjoy seamless comfort...
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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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First time offered - only property of its kind the keys -as featured in Global Mansion - Wall Street Journal. A true resort style peninsula surrounded by over 25 acres of park nature, providing the upmost privacy anywhere in the world.Web:Feel the joy of living on a truly beach home. ...
Featured review
We spent a month at this spectacular piece of heaven. It feels like you’re on our own island. Everything was laid out for us and the views anywhere on the property were breathtaking! One of our most...
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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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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: 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...
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...
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Come enjoy this beautiful OCEAN VIEW condo located in Key Colony Beach on the 2nd floor!!! This two bedroom & two bathroom condo offers all the amenities of home!!! Enjoy a cup of coffee in the morning, or a glass of wine anytime on one of the two ocean view balconies. Coin laundry right outside the...
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Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos...
Featured review
Beautiful sanctuary centrally located in Old Town. Very comfortable accommodations in a well maintained property. Property manager and Owner were very responsive to any questions or concerns that arose....
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...
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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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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Blue Shell is a delightful new canal front vacation home with a pool, just a minute to the ocean and open water and lots of fun amenities! It is also about 10 minutes from both Coco Plum Beach and Sombrero Beach.The dock is 50' and there is parking on the side of the house for truck and trailer....
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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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Welcome to your dream home in Key Colony Beach! This stunning, waterfront, half-duplex offers breathtaking views, a spacious open floor plan, and has been completely upgraded. With two bedrooms and two bathrooms, you'll have plenty of space to relax and unwind.The kitchen is fully equipped and...
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Key Colony Beach House with Cabana Club membership This is a spacious, canal water front, open layout, 2 bedrooms, 2 baths, ground level home that can accommodate up to 6 guests with plenty of room to spare. It is a short walk from multiple restaurants, bars, waterfront parks, and the Cabana Club. We...
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Lovely 1/1 condo in Coco Plum with pool, dockage and a boat ramp. This home is spacious and offers a pool and garden view from back screened in patio. You can enjoy a cup of coffee or a cocktail and enjoy paradise. It is just a very short walk to the canal and pool!The condo has a queen sized bed...
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