58,368 properties available

Located in Islamorada, Florida, United States. OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards "Windley Cottage" is a private home in the small gated community of Angler's Reef in Islamorada. This welcoming, tastefully-decorated home is located at mile marker 85, away from the highway , and just steps from the pool and docks. The “Bahamian conch style" home provides irresistible charm and comfort tucked in among lush landscaping. Whether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer! Its central location is perfect for exploring all of the Florida Keys!We have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our paddle boards or kayaks. Cycle to the many gift shops and restaurants on our beach cruiser bikes. Scuba or snorkel the nearby coral reefs and shipwrecks, rich with underwater wonders. Fish or dive near the popular Alligator Reef Lighthouse, which is visible

Located in Tavernier, Florida, United States. Clean, Fully Remodeled, stocked Houseboat, Great Wifi! Luxury on the Water Very spacious, Comfortable and "super clean" Houseboat. “Baycation” is a 44'x15' triple level upper deck Houseboat completely remodeled. She has one master bedroom with queen size bed, very comfortable sleeper couch, and extendable single sleeper. Full bathroom with very spacious shower. Complete with all toiletries and options of sunscreen if you forgot :)And YES, everyone asks. There are 3 mirrors on board, one full length.The galley is equipped with all your needs from home; Manual and electric wine opener, cocktail mixer kit, blender and charcuterie boardYour cooking options are a BBQ Weber grill, convectional oven, plug in griddle and NUWAVE induction stove top. Microwave, coffee maker (with coffee and filters) and a Keurig machineRefrigerator/freezer, beer/wine/water cooler and Ice maker.All plush towels and linens...more than you will needThere are also very clean bathrooms available righ

Located in Tavernier, Florida, United States. An adorable, decorated studio apartment Summer Sea #333 - An adorable, decorated studio apartment that has everything you need for your stay in the keys. Summer Seas is a gated complex, and it offers a great pool, beach, work out room, game room and billiards. Its bayside location you will allow you to enjoy the spectacular keys sunsets. Summer Seas Condo is centrally located for convenient access to shopping, dining and attractions. Great condo for your next get away. ** This complex has shared coined laundry on each floor. If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacatio

Located in Islamorada, Florida, United States. Charming oceanfront condo with pool, beach access, tennis, & washer/dryer Escape to the Keys A6Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape the hustle and bustle of everyday life in the tropical Florida Keys, where tranquility and fun await. This condo is steps away from the water, with all you ever need for entertainment in a 10-mile radius. Tour the area and check out Rain Barrell Village, Theater of the Sea, the History of Diving Museum, or the Laura Quinn Wild Bird Sanctuary. Spend your days on the water participating in fun rentals and excursions like paddleboarding, snorkeling, surfing, deep-sea fishing, and every other waterfront activity imaginable. Shared amenities include a tennis court and a glittering pool on-site.Upon entry, you'll be met with a bright interior filled with natural light thanks to the floor-to-ceiling windows, and a warm feeling of welcome throughout the space.

Located in Islamorada, Florida, United States. Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach. - VR#258 - Saturday check in preferred, message for alternate days. 2 bedroom and 2.5 bath at 117 Anglers WaySlip available for rent for the week of 6/22/2024 & Mini Season 7/20/2024. Message for details.Awesome family get-a-away in beautiful Islamorada. The ocean views from the back decks are amazing. The Oceanfront pool is serene! The gated community is a family friendly immaculately kept flora fauna park-like setting. Perfect for evening strolls or a bicycle ride. Located in walking distance to swim with the dolphins at Theater of the Sea and local restaurants and bars, Anglers Reef is the perfect family get away for boaters, kayaker's, paddlers, foodies, historians, honeymooners, couples, snowbirds or anyone that wants to experience the Florida Keys.There is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as

Located in Tavernier, Florida, United States. Starfish -1 bedroom 1 bath apartment with full kitchen in Islamorada, Florida. The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From SCUBA diving, to kayak eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer.

Located in Islamorada, Florida, United States. Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach Paradise is only a click away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation rentals. Our unit has unobstructed direct ocean views, and overlooks the resort style swimming pool. Dock space is available to rent as well for boats up to 31 ft. This home is great for a family vacation. There is also a beach and kayaks available. Lush, tropical landscape adorns this property.

Located in Islamorada, Florida, United States. Cozy Studio on Oceanfront Property with Pool Treehouse Cottage - The Treehouse is the upper level of Hawksbill Each cottage has it's own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards and more. This cozy studio overlooks tropical landscaping and has a very private feel. It features a king-sized bed and kitchenette. The Treehouse Studio can be rented separately or in combination with any of the other three homes.Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit car

Located in Islamorada, Florida, United States. Renovated - Boat slip, pool, beach - Anglers Reef oceanside gated community Palm La Mar, a luxury vacation rental located in the exclusive oceanfront gated community of Anglers Reef in Islamorada, Florida, "The Sportfishing Capital of the World".The two story Key West style house has 2 master bedrooms on the second floor, furnished with king beds, ensuite bathrooms, and private balconies. The first floor has a half bathroom, full kitchen, dining room, and living room with sleeper sofa. The gated community of Anglers Reef offers a resort feel with detached villas, quaint streets, a 75 foot heated pool overlooking the Atlantic Ocean, and two private beaches. The property is neighborly, safe, and immaculately landscaped for pleasant walks day and night. Anglers Reef is in close proximity to restaurants, Starbucks, entertainment, bars, and water activities, many within walking distance. There is a private marina on a deep channel directly out to the Atlantic Ocean. Not all homes at Angle

Located in Tavernier, Florida, United States. Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys Capt. Craig’s Guest QuartersThe Dolphin Suite is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities.Freshly remodeled with the traveler in mind, enjoy our little piece of paradise-minutes from all that the Upper Keys has to offer.

Located in Islamorada, Florida, United States. Discover the Charm of Island Living Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 4 people. Stay in touch with family & friends with free wireless internet. The master bedroom has a king size bed with two twin beds in the 2nd bedroom. If your children are small, we have a hi chair and various toys, Cd's and games. Our condo has a newly renovated kitchen with quart countertops, stove, dishwasher, microwave, coffee maker, blender & breakfast bar. All linens & utensils are provided. There is a separate dining room that seats 5 people. Vacation Rental License #VR-24-0316

Located in Islamorada, Florida, United States. Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home Time to change your latitude, attitude and immerse your body and mind in the calming, soothing waters that surround our home in our Florida Keys paradise. View amazing nightly sunsets from our sandy beach, fish or relax on our NEW pier, dip into the heated pool, take our bikes for a ride to large park right next door, and slide over the water on our kayaks.Limited vacation days? You can simply work remote from our TWO ready-to-go fully functional high-tech fastest fiber-optic internet offices.First time to Keys? No worries, I will guide you with lots of fun ideas. For questions and awesome Keys vacation activities find me, Jose, at GoToKeys.QUICK OVERVIEW:We offer you our clean 2 bedrooms (king beds) with an extra bedroom space and 2 full bathrooms. Our townhouse sleeps 5 to 6 very comfortably. Extra charge for more than 6 guests. Our townhouse is nicely appointed with a full kitchen, living room, dining room

Located in Islamorada, Florida, United States. Family/Pet Friendly Venetian Shores Home This beautiful Venetian Shores pool home with plenty of space to relax and play. Situated on a deep water canal with quick access to the Atlantic Ocean and Florida bay. The property offers lush tropical landscaping, 100 foot dockage. Outdoor covered living area with grill, dining table, and TV. The main floor has 1 master king with shower, and 2 additional bedrooms all with twin beds and bunks with bathroom. Anchors Away Boat Rentals can have a boat delivered right to the dock for your stay! 28 day minimum rental requirement.

Located in Islamorada, Florida, United States. ULTIMATE outdoor living area at this 4/4 canal home with pool! This beautifully remodeled home in desirable Plantation Key Colony has the sought-after amenities of a large resort, in your own private setting. With two separate living spaces, this home is great for larger families or groups of friends wanting to vacation together while also enjoying their own space. Both the upstairs and downstairs living spaces feature full kitchens, living rooms and washers and dryers. The main living space is located on the second level and comfortably accommodates 6 guests with three bedrooms and two bathrooms. The bedrooms are well appointed with a king ensuite, an additional bedroom with full and twin trundle beds, and a third bedroom with two additional twin trundle beds. A shared bathroom is located in the hall between the second and third bedroom. The guest apartment is located on the ground level of the home, providing accommodations for two additional guests. The entire home features high-end

Located in Islamorada, Florida, United States. Beautifully Renovated 2 Bedroom Condo Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the community's two tennis courts, along with two bedrooms, both with en-suite bathrooms. All you'll need is your toothbrush and a swimsuit, and you're all set for a fabulous Florida Keys vacation. The Futura Yacht Club HOA charges- onsite-$150 per trailer and $50 per boat fee. These fees will not show up on your rental agreement, as the fees are collected upon check in at Futura Yacht Club. If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. VR-24-0333 Per Islamorada's vaca

Located in Tavernier, Florida, United States. Salty Suites, simply put, it's paradise 365 days a year. Salty Suites is simply paradise 365 days a year. Located in the fishing capital of the Florida keys, Islamorada. This peaceful 2 bedroom, 2 bathroom oasis will help you forget about life for a while. Minutes away from the finest restaurants and a short boat ride to Snake Creek and Tavernier Creek. Watch the manatees from the 60ft dock and the best sunsets in the world just 1 block away. Plenty of space for your small boat, trailer, or RV.*28-day minimum stay.

Located in Tavernier, Florida, United States. A 57-foot trawler in Islamorada Located in a friendly marina with a restaurants, gift shop, tiki bar, kayaks, jet skis, and charter fishing boats minutes away.----------------------------------------------------------------------------------------------------

Located in Tavernier, Florida, United States. Relax in Islamorada-Canal Front 3 Bedroom / 2 Bath Home Relax in Islamorada Canal Front 3 Bedroom/2 Bath Home Spacious Keys style 3 bedroom / 2 bath home located on deep canal at Tavernier Creek on Plantation Key. Centrally located on MM 90, just an hour from Miami. Located south of Pennekamp Park and one mile north of Founders Park where you can enjoy many facilities such as: Olympic-size pool, skateboard ramps, baseball and softball fields, basketball, tennis, beach, playground, walking and bicycle paths, and much more. House is just minutes from major prime fishing and diving areas, shopping, movie theatre and great restaurants. The home has large concrete dock with fish cleaning station. Tiki bar with outdoor Jacuzzi, portable gas grill and pool table. Has quick ocean access via Tavernier Creek. Amenities include: Fully equipped kitchen, microwave, dishwasher, big screen TV in living room, TV’s in Tiki and master bedroom, DVD, washer & dryer. Master bedroom has a king bed,

Located in Tavernier, Florida, United States. New Construction home. 50' Dock w/ Pool & Hot Tub. Just S. of Tavernier Creek This beautiful Conch style home was completed in 2019. The house is a 2000 sq ft. 3 bedroom 2 bath home, each of it's 3 bedrooms has a king bed. There is private parking out front for vehicles and a 50' dock out back. The yard boasts a luxury pool with tanning ledge and hot tub as well as an outdoor kitchen. Also included is a 500lbs commercial ice machine. The location is ideal for boating allowing quick access to both the ocean and bay.

Located in Islamorada, Florida, United States. SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA! Just under 1.5 hours from Miami International Airport, you will find the beautiful gated community of Executive Bay Club. This townhouse has 3 bedrooms, 2 full baths, and a private patio with bbq. The unit has been beautifully renovated, decorated, and has all the comforts for a relaxing vacation. Amenities include a private beach, dock, pool, clubhouse, tennis courts, as well as 24 hour security. It is surrounded by amazing restaurants, shops, and spas. This vacation oasis is right next door to Founder's Park /Yacht Harbor and Marina. Whether you want a relaxing getaway or a vacation full of outdoor adventure, Islamorada Florida has the best of both worlds. Come stay with us and see for yourself!

Located in Islamorada, Florida, United States. Latitude Adjustment FLKeys Latitude Adjustment, Islamorada, FloridaThis home is our families' paradise in the Florida Keys and we want to share it with you. When our family is not using it, it is ready for you to make your own memories. This home offers much more than your average resort stay -- and is a perfect home base for all of your water activities:snorkeling, boating, and fishing.

Located in Islamorada, Florida, United States. Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled.... everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! Luxury heated pool / spa! Surrounded by a spectacular Dominican coral paver deck that does not get hot and has superior non skid properties! 20K Insane resort quality landscape lighting package installed in 2021. The home sits on a huge 70 x 100 foot lot (almost a 1/4 acre) on a crystal clear deep water canal just off world famous Snake Creek which takes you to the Atlantic and beautiful Florida Bay in just minutes. A one of a kind professionally designed lush tropical keys landscape creates an ambiance that you will enjoy and never leave as it gives you the feeling of having your own private resort all to yourself. Custom made and extremely comfortable Adirondack chairs and chaise lounges,

Located in Tavernier, Florida, United States. Islamorada Keys Waterfront .Pool Luxury Home Waterfront Islamorada 4 bedroom 3 bathroom home on the absolute best Waterfront Deep Water Canal w direct ocean access. Bring your boat or rent one locally and spend your keys vacation in paradise. Spacious Dock area .This home has a Pool, pool table, King size beds, Wifi, Gated yard, Flat-screen Tvs, BBQ, screened porch , washer and dryer. Located near the best restaurants and shops. Free access to Founders park and beach , Plenty of parking.Note:5% monroe County tax will be collected seperatelyBus Tax ID #138028Tourism Tax Acct Active(Boat Lift Use available at extra fee)Small pet considered. please inquire with details.

Located in Tavernier, Florida, United States. Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock. Location, location, location! A tropical palmy dream and playground for ocean lovers.Minutes on boat from the best sand bars, fishing and diving spots in Islamorada. The property is a beautiful and charming water front house, which has been newly renovated with a light, open and airy tropical Florida Keys feel. The newly landscaped and tropical back yard that precedes its 65' of dock (partial for docking) will immediately transport you to your own personal Margaritaville. Situated by the entrance on a wide canal right off Tavernier Creek, this home’s location offers you very easy and quick access to the ocean and bay. The property is homey, but also unique. It’s structure is made up completely out of concrete and its linear architecture design delightfully compliments an outdoor pool on the 2nd floor, offering you great water views from the pool deck, interior of the home, and inside the pool.Upstairs has two bedro