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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...
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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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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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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...
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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 apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape....
Featured review
This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under...
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Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located...
Featured review
Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over...
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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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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...
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4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family-friendly and a fisherman's dream. Our home sleeps 8 with every comfort you would want while on vacation in the keys...Large...
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This is our third year at Blue Dorado. We love it here! Everything was perfect for our family. The access to the Ocean and Tavernier Creek is amazing. We saw so many beautiful sunrises and sunsets.
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Escape to paradise in this gorgeous 3-bedroom, 3-bathroom townhome is located at Executive Bay Club in Islamorada, FL. Ideal for family getaways or group vacations, this townhome offers two luxurious king beds and a trundle bed in the loft, ensuring ample space for everyone.Enjoy breathtaking ocean...
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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 my first time staying in Islamorada for the many years I have been coming to the Keys, and I must say, I am fully addicted to Islamorada! Islamorada is just not as "commercial" as the middle keys,...
Distance to beach: 4 miles to Anne's Beach
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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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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...
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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...
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Tea Table Key Private Island Estate and Wedding Venue An extremely rare and stunning private island, accessible by car, Tea Table Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada.Jutting into the blue-green waters of the Atlantic Ocean, Tea Table Key features a 2,000′...
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Introducing Maison Residences Unit 201, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean...
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Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach.Dockage can be obtainable through Islamorada...
Featured review
The home is meticulously clean and spacious. It has all the comforts of home. We cooked several meals and had everything we needed. The views from the balconies are amazing. The complex itself is well maintained....
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Mile Marker 75 – Bayside4 bedroom 3 bathPalm Cottage South, is a charming, modern home directly on the canal with a heated, private pool, dockage, and access to the Port Antigua community sandy beach. Dockage for 24′ boat max on the lift pictured.Elevated for great breezes and...
Featured review
Great house, pool, and area. Lots of attractions and wonderful restaurants. Also, great people to work with.
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Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating...
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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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JANUARY just opened up! Call today for January with a HUGE discount. CALL NOW! Popular Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world,...
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We have stayed in this unit on this property two years in a row and going back in February. Honestly can’t wait for our trip. The location of this unit is perfect with the spiral staircase for easy access...
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Mile Marker 83 – BayfrontWelcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.As you enter the home, you’ll...
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. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, and two floors facing the canal and a private sanctuary....
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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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Mile Marker 74 – Bayfront – Beachfront – Handicap Assessable – Dockage for 30′ boatThis amazing beachfront home is a must see! Located on one of the few white sand beaches in the Florida Keys, Gulfview is a private home located on Lower Matecumbe Key in Islamorada in...
Distance to beach: 5 miles to Founders Park
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Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees...
Featured review
My wife and I stayed at this 1 bedroom 1bath duplex on the water. It was perfect for the 2 of us. Clean. Owner was very attentive.
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This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-concept living, kitchen, and dining area flows effortlessly through the terrace to the backyard, where a private dock invites boating and fishing, and an outdoor bar and dining area offer...
Distance to beach: 5 miles to Anne's Beach
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Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath...
Featured review
Awesome peaceful location,clean and perfect amenities lots of birds and fish at marina manatee, sand sharks ,etc
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Beautiful bayfront house, private pool and dock, right in Downtown Islamorada Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern finishes meld with traditional Key West style, Coral Cove 8 offers island living in style. This retreat is...
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Mile Marker 77 – Oceanfront – Lower Matecumbe Key.Six bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach,...
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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
Great facility for those with a boat! Each slip has electric and water wash down. The people at the Futura will go out of their way to help with fishing spots ( thanks Brian), restaurants, attractions....
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Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —Units 201 and 203 rented together. Private steps to pool, beach and Atlantic Ocean! 8 bedrooms, 8 full baths, 2 half baths, 2 full kitchens, 2...
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Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of...
Featured review
We stayed here in the “Honu Hale” house in August 2024 during the Florida Lobster Season. The property is ideally laid out & set up for boaters, divers & fisherman. There’s plenty of dockage and a...
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️5 bedroom 4 bathrooms (One bathroom by pool) ️Canal home in Venetian Shores with access to bay and ocean ️100 foot of dockage on 100 foot wide deep canal. Ask about bringing your own boat ️Location of canal is off Snake Creek near MM86 ️ Beautiful large pool with hot tub in tropical setting ️...
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Mile marker 77. Deep Water ocean side canal with direct access to the Atlantic Ocean and a straight shot to Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. There is no cable package with this home so please bring your passwords for live streaming from the smart TVs.The...
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$15,000-$17,500 WeeklyA world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute...
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Ocean side pool home with private dock. Beautifully decorated with 2 bedrooms and 2 bathrooms on the main level. Master bedroom has a queen size bed and a full bath. The second bedroom has twin beds. Downstairs is a suite with sleeping accommodations for 4 people and full bathroom. Linens and towels...
Distance to beach: 5 miles to Anne's Beach
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Welcome to The Nest Villa & Marina in the heart of beautiful IslamoradaNestled on a picturesque 1-acre lot overlooking the stunning Florida Bay in the Florida Keys, the Nest Villa offers a perfect blend of privacy and proximity. This exclusive residence is one of seven privately owned villas,...
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My 18 yr old son and I stayed here at the end of September and it was a fantastic trip!We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen!...
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This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs...
Featured review
This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki...
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The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove...
Distance to beach: 4 miles to Founders
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Rare Summer Openings! Your Private Resort Awaits in IslamoradaIf you’ve been dreaming of an island escape with all the luxury of a high-end resort but none of the crowds, this is your chance.Your Own Private Resort in the Florida KeysFrom the moment you arrive, this estate feels more...
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Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking 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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PROPERTY NAME: The Bungalow House 32 Park Rd Islamorada, FloridaLocation: Bayside Very close to the Publix Shopping CenterMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedMile Marker : 82Details: This home is absolutely beautiful with your own pool and...
Distance to beach: 4 miles to Founders Park
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Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air...
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We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom...
Featured review
We had a wonderful month in Islamorada at this outstanding waterfront condo with pool and sauna, dock etc. The views were gorgeous from the 3 decks in this corner unit. The area is exciting and near both...
Distance to beach: 2 miles to Founder's Park
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Long-term rental available in the beautiful Venetian Shores community of Islamorada, Florida. This 3-bedroom, 2-bath home sits on a secluded plugged canal by the water. Enjoy a large master bedroom, a spacious open layout, and a generous outdoor deck ideal for entertaining. Additional features include...
Distance to beach: 0.9 miles to Founders Park
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Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom...
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We spent a month in Sharon's condo (January 2025). Upon arrival we had everything we needed for the month! She goes above and beyond stocking the kitchen, cleaning supplies, pantry etc. The bedrooms are...
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Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking...
Featured review
This condo was very conveniently located. We could snorkel at John Pennekamp and kayak the mangroves of Islamorado. Plenty of close good seafood restaurants in vicinity. Spend the day at Bahia Honda.
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Traditional coastal cottage styling built in 2017 and the Pool was added in 2020. Large backyard beach and only steps to the turquoise waters of the Atlantic Ocean. Kayak, paddle board, or kite ski from your backyard! Plenty of parking out front and private gated access; fencing around the perimeter....
Distance to beach: 2 miles to Founders Park
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*Discover Elevated Island Living at Sea Breeze 41 Luxury 3BR/2BA Condo with Private Boat Slip in Exclusive Coral Harbour Club, IslamoradaWelcome to Sea Breeze 41 — your personal slice of tropical paradise in the heart of the Florida Keys. Nestled within the highly coveted Coral Harbour Club,...
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We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you...
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Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.
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Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends....
Featured review
We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the...
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