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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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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...
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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...
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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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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 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...
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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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...
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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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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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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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...
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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$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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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 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...
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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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**SPECIAL** APRIL & MAY 2026 DISCOUNTED $1,000! 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, Islamorada. If you have...
Featured review
I had the pleasure of staying for the month of December. I've been staying in the keys during the month of December for the past 5 years and this is by far my favorite place! The condo was warm and inviting,...
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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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⭐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 ⭐...
Distance to beach: 1 miles to Anne's Beach
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Secluded Waterfront Apartment with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this...
Featured review
We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!
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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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3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2...
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PROPERTY NAME: Bella 109 Valencia Drive Tavernier, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Venetian ShoresMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 86DESCRIPTION: Luxurious 4-Bedroom...
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About this spaceWelcome to Angler’s Reef Resort Villas & Marina - a stunning Islamorada vacation destination. This two bedroom, two and a half bath conch house overlooks the resort style swimming pool and is available for weekly and monthly vacation rentals. Our home has ocean views, 2 spacious...
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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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PROPERTY NAME: Mango House 81212 Old Highway Islamorada, FloridaLocation: Ocean side located on the Old Road by Green Turtle RestaurantMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedMile Marker : 81Details: This home is absolutely beautiful with Keys...
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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...
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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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Seeing is believing. The Captain's Quarters is a direct, oceanfront home on the Atlantic shoreline of Islamorada. For your planned getaway, come enjoy truly private and relaxing oceanfront living in the heart of Islamorada, in a unique home boasting a treasure-trove of Florida Keys history. The...
Distance to beach: 0.5 miles to White Marlin Beach
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*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will...
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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Hi, nice to meet you!!! If you like to be somewhere surrounded by a magnificent peace and balance, fresh, organized and a very clean home, "you just found it". You will be happy to go out in the boat and come back to a relaxing home to enjoy the rest of the day with family or friends with...
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PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of White Marlin BeachMINIMUM STAY: 90 days, this is a 3 month minimumMILE MARKER: 74.5DETAILS: You will love this charming and cozy Keys Holiday...
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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....
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Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and...
Featured review
Spending the month of December at this beautiful condo with my family was an unforgettable experience. The condo itself was warm, cozy, and inviting, with all the amenities we could possibly need for a...
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PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated...
Featured review
Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient....
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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PROPERTY NAME: Martin Family Fish Camp 106 Madeira Rd., Islamorada, FloridaLOCATION: 2 Houses Located on a private peninsulaMINIMUM STAY: WeeklyMILE MARKER: 81.9DETAILS: The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each...
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...
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The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged...
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PROPERTY NAME: Casa Mar 115 Ponce de Leon Blvd, Islamorada, FloridaLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Port AntiguaMINIMUM STAY: 28 DaysMILE MARKER: 74.5 DETAILS:Stunning two-story, 3-bedroom resort-style, professionally decorated home. Inside,...
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Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and...
Featured review
Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt...
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Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also...
Featured review
This house is beautiful. Right on a canal where we kept our boat for the week. Manatees came by to visit daily. Caught keeper mangrove snapper right there. Neighbors were amazingly friendly. Everything...
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...
Featured review
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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PROPERTY NAME: Villa Riolo 130 Columbus Drive, Islamorada, FLLOCATION: Gated Oceanside House on canalMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.5DETAILS: "Villa Riolo" is an updated single family stilt home and perfect...
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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...
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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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