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Welcome to Villa Azzurra!This beautifully decorated, island style beach home can comfortably accommodate seven guests, and boast three en suite bedrooms, a fully stocked gourmet kitchen, private pool, endless water views, and a bayfront beach.The first floor offers a high quality kitchen...
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We loved Harbor Hideaway for our month long getaway to Islamorada. The home is beautiful with gorgeous sunset views and huge private balconies. The newly renovated bathrooms are fantastic! The outdoor...
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This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast....
Featured review
This is our second year staying in this beautiful home. Once again it was beyond perfect! Everything we could possibly need is here so you only need to unpack, sit back, relax & enjoy! The kitchen is...
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Welcome to Ananda Shala!Nestled at Mile Marker 92 in Tavernier, this beautifully appointed 3-bedroom, 3-bath bayfront retreat invites you to slow down from the moment you arrive. Inspired by the spirit of a “shala”—a space for practice, reflection, and mindful living—this home...
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Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms,...
Featured review
2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights...
Distance to beach: 4 miles to Anne's Beach
Key Amenities
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Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub,...
Featured review
Condo was well equipped and tastefully decorated in an appropriate style. Direct ocean views from a 50' balcony overlooking docked boots with the occasional manatee swimming by was exceptional. Location...
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Welcome to Paradise Palms!Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access...
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Welcome to Keezy Does It at Anglers Reef in Islamorada!A charming, oceanfront gated community in the heart of Islamorada, the sport-fishing capital of the world!Delightful Key West-style architecture entices you through the entrance security gates into this enchanting enclave of 52 private...
Distance to beach: 1 miles to Founders Park
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Welcome to Morada Breeze! This 6-bedroom, 4-bath bayside slice of paradise is ready to make your next vacation an enjoyable one. Located on Plantation Key in Islamorada, Morada Breeze has the amenities to elevate your trip to the Keys.Step inside to discover an expansive kitchen perfect for preparing...
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Introducing the "Bonefish House" at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed...
Featured review
A BEAUTIFUL LOCATION. This was a well appointed house which made for a wonderful stay for three couples. The house is listed for rental as four bedroom four bath. In reality two king bedrooms with bath...
Distance to beach: 3 miles to John Pennekamp State Park
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Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at...
Featured review
Great atmosphere, two minutes to the Atlantic. Jose great host, very clean. Thank you Jose for sharing your home.
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Welcome to One Ten Palms!Escape to paradise at this private oceanfront estate in Islamorada, where the laid-back spirit of the Keys meets resort-style comfort. Set on more than two acres of lush tropical grounds, the property is graced with 110 swaying palms and 250 feet of natural oceanfront beach,...
Distance to beach: 4 miles to Founders Park
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Welcome to Island Time!This newly constructed canal front residence located in the heart of Plantation Key is sure to help boost your serotonin and ensure complete relaxation. This impressive home can comfortably accommodate eight adults with four bedrooms and three bathrooms.The main living...
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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
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You will LOVE our condos.... location location, location! You'll love the waterfront heated and chilled pool during the summer! And it is a boater's dream! Great value and our reviews are awesome.The perfect set up for your boat and includes your own boat slip, ramp and plenty of FREE parking!...
Featured review
Location, Location, Location!This place was perfect for remote work or a relaxing vacation, with the boat docked just steps from the door. It truly offers the best of both worlds!Graceful manatees...
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5 Star Modern New Construction Bayfront Home With Private Dock and PoolIsland Dreamz Bay House is a piece of paradise on the Vaca Cut waterway in Marathon. Gorgeous and brand new 5 bedroom, designer decorated, 4 bath single-family home with 36 ft. of assigned dockage. Private pool can be heated upon...
Featured review
This was our second stay at Vaca Cut at The Tides. We loved this gorgeous home with its exquisite design and comfort. The house was immaculate ~ kudos to the pros who keep this home clean and well stocked...
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This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers...
Featured review
We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.
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The 3 bed/3 bath canal front home provides quick access to the Atlantic and Looe Key with no bridges.60' of canal front with 40' of seawall and a cleaning station.After a day on the water, enjoy the refreshing outdoor shower or soak in the large master bath tub.The screened patio...
Featured review
We really enjoyed our stay in this well appointed home. The location is an old Florida Keys experience. Great neighborhood with no thru traffic, friendly neighbors and great sunsets. The reef is a short...
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1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo...
Featured review
Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.
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In the heart of Tavernier lies this beautiful 2-bedroom condo that combines the Florida Keys' breathtaking scenery and lively atmosphere. Nestled just a short 19-minute drive from the renowned John Pennekamp Coral Reef State Park, this property offers the perfect base for your tropical getaway.As...
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Upon entering the home you’ll be greeted by laidback island decor and vast ocean views. The Tommy Bahama Tiki inspired apartment, over looking the marina located in the 5th building, offers two bedrooms and two bathrooms, Free Parking, High-Speed WiFi, Fully equipped kitchen- Washer and dryer. Self...
Distance to beach: 4 miles to Sombrero Beach
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Welcome to The Butterfly Cottage – Where Nature's Magic Meets Keys ComfortEscape to a truly unique Florida Keys experience at our certified Monarch Butterfly Garden sanctuary! This charming traditional conch cottage offers families a peaceful retreat where butterflies dance through native...
Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach
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Due to a change in licensing we are only available for monthly rentals. However I will consider offering a last minute deal pay for 3 and stay for 4. Please contact me directly.Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always...
Featured review
Top notch place in great location. Very clean. Would definitely stay in this unit again sometime in the future.
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The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny...
Featured review
I came to this house with friends, completely unsure what to expect from Key West. The island itself moves at this fascinating, slightly calm/chaotic pace, but stepping into this rental felt like entering...
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Welcome to our 5 bedroom with optional 6th bedroom home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxing vacation with family and friends 31 miles from Key West’s Mile Marker 0. This spacious 5-bedroom home is on a double lot with plenty of parking and 150 feet...
Featured review
We've stayed in this home for a month for 3 years, 2025 being our 4th year we added a month. We stayed in the home before Jeff and Christine bought it and loved it then. They've made so many improvements...
Distance to beach: 0.2 miles to Fort Zachary Beach
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AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all, she is close to the action, but far enough from the riff-raff :) Large front yard and porch to watch Key West pass by. Beautiful and spacious in/outdoors. POOL within...
Featured review
Shabby Chicken was absolutely perfect. From the location, amenities, interior , exterior, proximity to Truman waterfront , Fort Zachary beach and the Green Parrot. Marie (and Tom) were awesome. Karen and...
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This extraordinary island castle will make you feel like the royal family! With four bedrooms and five bathrooms you will not have to share your space! Start your day boating, fishing or kayaking and then return for a cool dip in the pool! Relax on the expansive screened in porch with a drinks and appetizers...
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INGROUND HEATED AND CHILLED POOL TO COME IN NOVEMBER!! Daydreamin’ blue in the super-desirable Summerland Cove neighborhood! There is plenty of room for family and friends here, with four bedrooms and a huge open concept kitchen and living room, you won’t ever feel crowded. Additionally, a...
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Keys Life Come on down to “Keys Life” and enjoy a great Florida Keys vacation. Located in one of the best deep-water boating areas. The crystal blue canals and superb deep-water boating will make your fishing days a dream. Great outside entertaining areas with a perfect pool to splash around...
Featured review
Enjoyed our stay at Keys Life. The home was beautiful. The weather was quite windy so we weren’t able to get out as much as we wanted in our boat but we were able to get some nice lobster! It was nice...
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This 3 bedroom, 2.5 bath single-family modern home is great for entertaining! Enjoy the outdoor area with a pool and a separate hot tub or catch a game of pool on the main floor. This home is located on the 63rd Street canal and being ocean-side, it's just a quick trip out to sea where you'll...
Featured review
Spent Thanksgiving week at The Keys Retreat. Perfect location, house was very clean and kitchen stocked with everything you need. Really enjoyed the outside area in the pool and jacuzzi.
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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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Bitter End Vacation Rental –This Summerland Key beauty is the one you have been looking for. Located on Summerland Key with superb boating and access to deep water. Just the perfect spot to see sunset views and peaceful water vistas. Feel free to bring your pet along too!!The interior is...
Distance to beach: 3 miles to Sombrero Beach
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*Modern updates, new furniture, new docks, pool etc- updated photos on mgmt site!* A spacious bayside 3 BR 2.5 BA retreat within Indigo Reef, a private resort community of Marathon FL- offers many extras for anglers, families, snowbirds, or tourists! Beautiful views from both levels of canals, spacious...
Featured review
Our stay at Indigo Reef was fantastic. Perfect weather and a perfect location. The unit had everything that we needed and was very comfortable for 5 adults. We truly hope to be back for a longer stay in...
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Casa Atlantic is located in the upscale Casa Marina District on a quiet shrub lined street that has very little traffic because it is not a through street. This luxury house that was built in 2013 with 1,672 sq. ft. of finished indoor space has everything that is needed, except refreshments and food....
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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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DescriptionAdorable two bedroom, two bathroom half duplex on stilts overlooking the extra wide, deep canal and the Par 3 Golf Course on the streetside. This home is tidy and spacious. It offers soaring ceilings, tons of natural light, lots of covered seating, a beautiful concrete pool, 37 feet of...
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3 bedroom, 2 bath gulf front home with amazing views and meticulously manicured lot.Amazing Gulf and sunsets views from almost every room in this tropical retreat! The Palm Tree Resort is a private gated, three quarter of an acre resort located directly on the Gulf in a premier section of Morton...
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Mermaid House was just recently renovated and is a brand new second level vacation rental! This home is in a great central location, not far from Winn-Dixie, Bahia Honda State Park and Key West!Decorated with a warm coastal feel, this home has an open floor plan with large glass windows! The home...
Featured review
I cannot say enough good things about our month-long stay at Mermaid House, so I'll keep it simple, just book it!!! The outside living area was our most favorable spot. (There is one caveat... be VERY...
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Experience the epitome of coastal living in this exceptional half-duplex located in the prestigious Key Colony Beach. Situated on the picturesque blue waters of Key Colony Beach, this property seamlessly combines modern luxury with the relaxed charm of island life. With 3 spacious bedrooms and 3 beautifully...
Distance to beach: 3 miles to Sombrero Beach
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Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water canal with easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas with canal views, cozy sunroom...
Featured review
Thank you . We had a great time..we fished, snorkeled and spent a wonderful time with family and friends.. we all highly recommend!!
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Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home...
Featured review
Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows...
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Welcome to Paradise Palm, a home away from home that encourages outdoor fun and relaxation with its unforgettable exterior amenities! Nestled in a quiet neighborhood, this beautifully furnished home offers a perfect blend of comfort and luxury.Step outside and be greeted by an excellent space that...
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Quiet, secluded townhouse that has amazing views of the tropical surroundings. The unit has two levels, so that no one is living above or below you. The two spacious wrap around decks reveal the Canal feeding in from the Gulf of Mexico and the heated swimming pool. There is a large 10 slip Gulfpointe...
Featured review
Great place to stay . Good location. Very nosey tenant's made the stay a little uncomfortable at times.
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Welcome to Morton Street Charmer! This coastal cottage, nestled on the open Gulf of Mexico, offers 2 bedrooms and 2 bathrooms, with recently updated furniture for a fresh feel. Enjoy stunning water views and unforgettable sunsets from the spacious dock, perfect for boats up to 30 ft. Don't forget...
Distance to beach: 9 miles to Coco Plum Beach
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Our vacation rental is an historic 1 BR/1 BTH waterfront cottage in prestigious Duck Key in the Florida Keys. There are plenty of outdoor amenities on the more than 1/4 acre property. These include a 15 X 34 foot saltwater swimming pool, hot tub, and grill with prep and dining area. The backyard perimeter...
Featured review
Great communication with the home owner. The cottage and yard extremely clean and well kept . Duck Key is the jewel of the middle keys and this property is of unequal value. Can’t wait for our next...
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This charming property offers 3 bedrooms and 2 bathrooms, ideal for families or groups looking to enjoy the beauty and tranquility of the Florida Keys.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Bird of Paradise offers stunning views of the Atlantic Ocean. Bird of...
Distance to beach: 7 miles to Bahia Honda State Park
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This newly remodeled home is cozy, yet spacious.This open concept, single family home is located on a canal and just a few seconds from the ocean. Fully furnished with Keys-inspired touches, this home comfortably sleeps 6 people with 3 bedrooms and 2 bathrooms.Spend the day at Bahia Honda State...
Featured review
We stayed in the rental for February and March of 2024 and loved it.Very quiet with friendly neighbors.Wonderful outside area and perfect boating with easy access to the ocean or gulf.Already have our reservation...
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Welcome to the Key House, a completely charming, canal front home located in the ultra popular Jolly Roger Estates on Little Torch Key.A cute tropical them from the outside in, you know you are in the Florida Keys! The exterior boasts an immaculately kept grounds with ample storage for your gear,...
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Sunset TidesExperience the ultimate Florida Keys getaway at our luxury waterfront vacation rental in Marathon, FL. This spacious 5-bedroom, 4-bathroom home offers breathtaking open water views of the Gulf of Mexico and Atlantic Ocean, a private heated pool and hot tub, 30-foot dock with power and...
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Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for...
Featured review
We stayed in unit 102. Glenn was a great guy to rent from, very helpful and followed up for any questions.a very nice condo, private bathroom for two main bedrooms. Most everything needed for making meals...
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Welcome to Palms & Pina Coladas where you will enjoy a beautifully remodeled waterfront paradise. Located in coveted Cudjoe Gardens, this ground level home comes equipt with everything you need for a relaxing Florida Keys Vacation (Including being able to use our Clear 2 seater Kayak). Private heated...
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