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Welcome to Oasis4rent!Escape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully appointed homes sit directly on the Atlantic with 200 feet of sandy beachfront, a heated saltwater infinity pool, and views of Alligator Reef Light on the horizon.The PropertyMain...
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: 1 feet to on property or at Founders Park
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Beautiful new home on Florida Bay with sandy beach, spacious pool, beautiful views, and sunsets every night. The home accommodates up to 12 guests. Each suite can be rented individually or combined. Please note that there is no smoking and no pets.Sitting on an acre with 6 bedrooms, 7 and 1/2...
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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Stunning rooftop views from this gulf side Tuscan style Villa3 Bedroom 3 Bathroom Freestanding villa located in Bougainvillea, a Gated Community, with a pool exclusive to Bougainvillea Clients overlooking The Gulf of Mexico.There is Great Fishing at this location! You can bring your boat in for...
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Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach
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Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always received great reviews on cleanliness and the bright citrus pallet is welcoming, there are 2 bedrooms (1 King & 1 Queen), one bathroom with couples walk in shower, The small but...
Featured review
Top notch place in great location. Very clean. Would definitely stay in this unit again sometime in the future.
Distance to beach: 4 miles to Sombrero Beach
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Come stay with us! Why?71 FIVE STAR reviews!! It's literally the highest number of reviews for ALL properties listed here on !!! That's right ALL OF THEM!Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation...
Featured review
Excellent location, clean, great accommodations. Easy check in/out. We all enjoyed the view and the pool and sandy area. We did not get time to partake of the hot tub and other amenities but definitely...
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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!
Distance to beach: 3 miles to Anne's Beach State Park
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About this property
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...
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The South House is a superb vacation home on Summerland Key. It offers everything you need to make your Florida Keys vacation truly memorable.The downstairs pool area is private and serene. There are several lounging areas to enjoy suntanning or wonderful afternoon shade. The crystal blue pool is...
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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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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What a great sunset view from this house! Fun in the sun surrounds this spot right on a wide canal with excellent access to fishing either the Gulf or the Atlantic side. Any outdoor enthusiast would be content here as the boating, diving, snorkeling, or kayaking is right out your back door.After a...
Featured review
This house has just about every and anything you could need. Very quiet and nice area. Owners went out of their way to ensure our stay was as stress free as possible! We had a 19’ boat docked at the canal...
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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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This home is a unique tropical paradise in Key Largo. Our kids named it Manatee Corner because it sits at the end of the canal and is often visited by friendly manatees. It is a large three-story duplex with a wraparound balcony. It has a canal that leads right out to the Atlantic, minutes from incredible...
Featured review
I rented jan.-mar and was very pleased with my accomodations. My rental was clean, spacious, and very naturally lit by all the large windows throughout. The owner was an absolute joy to work with. He even...
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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.
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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BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado's These boats are set up with everything you need to fish the Keys,...
Featured review
The location of Southern Sunset couldn't be more perfect. Only 25 minutes to Key West, 5 min to a great little grocery store called Murrays (and maybe 15 min to Winn Dixie), a short drive to Capt Hooks...
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Florida Keys Vacation Rentals – Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 in this 3-bedroom 2 bath Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine channel, gulf side. All the rooms are spacious...
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Privacy galore at this great location on Sombrero Beach Rd with a brand new POOL! Famous Sombrero Beach is approximately half mile down the dedicated bike path from this stilted 3 bedroom single family pool home with dockage! Open concept living with expansive decks on both floors that boast open water...
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Named one of the most romantic destinations in the world, this Magnificent brand new home in the heart of Islamorada is nestled between Cheeca Lodge Resort and Caribbean Resort offers a unique and luxurious experience for those looking for a private getaway. This 4 bedroom/4.5 bath home services from...
Featured review
Had a great time! The house was amazing and well-appointed. We grilled, we cooked, amd we walked to several great dinner spots. The pool was excellent with the grandchildren. Highly recommended!
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Welcome to Infinity Bay Islamorada – an infinite paradise with endless possibilities in the heart of the Florida Keys. This exclusive estate embodies sophistication and serenity, where guests can unwind in style against a backdrop of Florida Bay and swaying palm trees. At Infinity Bay, luxury meets...
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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...
Featured review
The house was beautiful. Well stocked with all things anyone would need. Pool was perfect- we did add heating as we have small grands that wanted warm water!! We loved it and will be back next year!!
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Florida Keys Vacation Rentals – Need a private space to call home during your sunny stay in the Florida Keys? Conchy Joe’s is the place! This beautiful home has 3 bedrooms and 2 bathrooms. The interior is fully furnished and decorated in Florida Keys fashion with plenty of space for friends...
Featured review
Always enjoy our stays in Keys when we find such a lovely place to have family come to join us. Some homes have a great location some have great amenities, but finding one like this, that has both is...
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Charming Canal-Front Retreat in Key Colony Beach with Exclusive Inch Beach AccessEscape to paradise at this stunning 3-bedroom, 2-bathroom canal-front home in the heart of Key Colony Beach. Perfectly positioned to offer breathtaking water views, this spacious retreat is the ideal vacation getaway...
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...
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...
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Summer never ends in the Florida Keys! Endless Summer is located on Summerland Key in the very desirable Summerland Cove neighborhood. This is a two bedroom, two bathroom comfortable home with additional and very accommodating living space on the lower level.Upstairs is open concept living with a...
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Welcome to your private slice of paradise in Key Largo. Nestled in a quiet, well-protected canal-front neighborhood, this beautiful four-bedroom home offers the perfect escape for those seeking comfort, space, and the laid-back charm of the Florida Keys. Designed to accommodate up to 10 guests, the home...
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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Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles)....
Featured review
We enjoyed our stay. The house was clean and had all those things (towels, beach toys, pool, kitchen essentials) that we were hoping for with our stay in Marathon. The location is great- walking/biking...
Distance to beach: 17 miles to Bahia Honda
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Looking for a vacation rental to get away from it all in the Fabulous Florida Keys? Look no further than our beautifully renovated home with open water and sunset views! This home has three bedrooms and two full bathrooms, open floor plan with designer kitchen and views from every room! You can enjoy...
Featured review
House is very spacious and open. Open water views and unbelievable deck for sunsets. Neighbors very welcoming and friendly. Already booked for next year
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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...
Distance to beach: 2 miles to Sombrero Beach
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Our waterfront, single-family home, affectionately named “Turtle Cove”, offers 3 bedrooms, 2 baths, and dockage with quick ocean access! This tastefully furnished Keys home is located on a quiet side street in a residential neighborhood on the Atlantic side of the Island, just 5 houses from...
Featured review
Turtle Cove is our favorite place in the Keys. The prime mid -Keys location is perfect for exploring. There is easy access to a variety of restaurants and attractions. The best being the "blue"; blue water...
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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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Casa Feliz~ Experience, enjoy, relax, and rejuvenate in luxury accommodations on the Atlantic Ocean.~ Secluded sophistication can be your vacation destination.Welcome to Casa Feliz! We are located on the quiet Grassy Key in the middle of the Florida Keys.Concierge Level Luxury vacation...
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Cute, 2 bedroom half duplex located on beautiful 8th Street in Key Colony Beach. Extra wide canal and 37 feet of deep water dockage! Shaded dock area perfect for cleaning your catch of the day. Just minutes through the tranquil Key Colony Beach canals to the open Atlantic and Vaca Cut to access the open...
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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...
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This charming family-friendly residence in Duck Key presents a spacious and inviting environment, featuring three comfortably appointed bedrooms and three modern bathrooms, making it an ideal choice for a memorable getaway. Each bedroom is thoughtfully furnished with a plush king-sized bed, ensuring restful...
Distance to beach: 1 miles to Anne's Beach State Park
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This Condo sleeps 4 and 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. Newly refurnished and refurbished,...
Featured review
This two bedroom apartment in the beautiful Bay Harbour condominium was special. The views of the ocean and the apartment complexes marina were exceptional. The apartment was well stocked with all the cooking...
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...
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''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house...
Featured review
My stay at our little piece of paradise was nothing short of AMAZING. This homey, cozy stay is the best possible place to come back to and spend time with family and friends after long sunny days spent...
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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!
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...
Distance to beach: 0.5 miles to White Marlin Beach
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Bring your boat!Nestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. Heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, and two floors facing the canal and a private sanctuary....
Featured review
We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has...
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"The furnishings/decor are beautiful. This is one of the nicest houses we have had the pleasure to rent, everything is spotless/brand new. It was hard getting our kids ages 8 and 10 to leave the house each day for adventures. " -Kristie KruegerAs a boating enthusiast, I designed Captain's...
Distance to beach: 4 miles to Founder's Park
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Welcome to Sunset Oasis!This beautiful bayfront retreat offers a rare blend of comfort, style and waterfront living in the renowned Indian Mound/Plantation Key community.This is a monthly rental. Flexible rental dates. Property is reserved from 11/1/2026 through 3/31/2027.Sunset Oasis is...
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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...
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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: 3 miles to Founders Park
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Welcome to Blue Palm Oasis!Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantation Key in Islamorada. This contemporary Keys villa seamlessly blends modern comfort with laid-back island charm, making it the perfect place to unwind, recharge, and soak up the sun....
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