Vacation Rentals By Owner In Islamorada, FL

Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are also just minutes away from a beautiful private beach that you can only access by water. Famous Alligator Reef and Tennessee Reef are just 15 minutes away. This is a beautiful boating, fishing, snorkeling, scuba diving or just relaxing paradise.brbrWithin walking distance you have Anne’s Beach. Also, within walking distance you have Caloosa Cove Marina and a convenience store which offer fuel, fishing supplies, bait, etc. You also have the famous Safari Lounge which was recently beautifully renovated.brbrThe house can accommodate up to 10 people comfortably. Upstairs you have 3 bedrooms and 3 full bathrooms offering a split plan for privacy. All of the bedrooms have access to a fully furnished balcony overlooking the canal. Downstairs you have a studio with a full bathroom, queen sofa bed, TV, wine cooler, bar area, refrigerator and microwave. There is plenty of natural light that enters through all of the large windows and glass doors throughout the house. brbrOutside the house offers a covered terrace with plenty of fans. The terrace is fully furnished and has a TV where you can watch your favorite sports games and/or favorite shows from inside the pool or the comfortable sitting area. Downstairs you have plenty of room including a pergola with a BBQ, 2 freezers, industrial size ice maker, a refrigerator and plenty of storage for all of your fishing gear. From your private dock you can fish, watch the manatees, sea turtles and pelicans.brWith just 90 minutes south of Miami Islamorada is a paradise your family will love to explore by land or sea with plenty of things to do including some of the best restaurants and shopping in all of the Keys.brbrIf you have a large vessel the property has a 65 Ft dock across the street with water and shore power that can be rented for an additional charge.

Our Happy Place Paradise in Islamorada with Heated Pool and 90 ft Dock

Islamorada, Florida, United States

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$371.29

Experience paradise like a local in this superb 2-bedroom 2 bath Villa with private patio and your own on premises boat slip and launch site. Master bedroom includes a king bed, the guest room has 2 twin beds, while the living room offers an additional queen sofa bed. Air conditioned, WiFi, washer/dryer, fully equipped kitchen + outdoor grill. All linens plus beach towels are included. Topsider Resort offers an exclusive private sand beach perfect for snorkeling, sunning and relaxing, Fish directly from the Topsider dock which is also the place to be for the evening sunset celebration. Other amenities include heated pool + Jacuzzi, tennis/pickle ball courts and complimentary kayaks and bicycles for your use. At mile maker 75.5, Topsider is perfectly located to enjoy the best of the Florida Keys,

Hotel Resort

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

Islamorada, Florida, United States

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Bath

Sleeps

$200.2

Just reduced for last minute Spring Break family!! Enjoy Townhome in the heart of the Florida Keys, under 1.5 hours from Miami International Airport, at 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 for less and see for yourself!

Spring Break in the Sun! Islamorada townhome w/ beach, pool in gated community!

Islamorada, Florida, United States

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$1333.49

Nestled between the Cheeca Lodge and Caribbean Resort, discover our exclusive 4-bedroom oceanside sanctuary, delivering an unparalleled beachfront retreat. Indulge in the opulent comfort of each generously appointed bedroom and its accompanying en suite bathroom. Designed for hosting memorable gatherings, revel in the convenience of a fully equipped kitchen and an outdoor grilling area. Bask in seclusion with your own private pool and patio seamlessly integrated with the living space. brbrPlease note, the property is located in a brand new development with ongoing construction on the houses closest to the water. Our house is located in the center of the development, therefore, the construction should not interfere with the vacation experience.

Seaside Sanctuary in the Heart of Islamorada

Islamorada, Florida, United States

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$266.26

Imagine waking up to warm ocean breezes, the gentle sway of palm trees, and the first golden light of the sun rising over the Atlantic. This is not just another day in paradise – this is your new way of living, breathing, and unwinding in the world-famous Florida Keys, known as the Sport Fishing Capital of the World. Whether your dream vacation includes world-class fishing excursions, snorkeling through coral reefs, paddling across turquoise waters, or simply relaxing in a private island oasis, your stay at our luxury resort-style 2-bedroom, 2-bath Seabreeze home promises an unforgettable experience. NO PETS ALLOWED.brbrPerfect for Monthly Stays & Extended RetreatsbrThis property requires a minimum stay of 28 nights, making it perfect for:brbr* Remote workers seeking serenity with high-speed internetbrbr* Retirees looking for extended winter escapesbrbr* Families wanting more than a vacation—those craving island livingbrbr* Adventurers who want the Florida Keys lifestyle at their doorstepbrbrPet-friendly units are available upon request (please contact the resort for availability and approval).brbrABOUT THE HOMEbrbrThis 1,230 sq. ft. Seabreeze model has been intelligently designed to offer both privacy and connection, style and function, coastal elegance and home-like warmth. It’s not just a rental—it’s your very own island residence.brbrKey Features:brbr2 Bedrooms / 2 Full Bathrooms – One bedroom is located on the first floor (ideal for convenience), and the second is upstairs for ultimate privacy. Both living spaces offer sleeper sofas to accommodate the whole family.brbrLoft Lounge & Wet Bar – The second-floor lounge features a sleeper sofa, wet bar, entertainment area, and opens to your private deck with spectacular Resort and Atlantic Ocean views.brbrFully Furnished, Coastal Inspired Décor – With a light, breezy tropical theme, each unit is individually decorated by its private owner, ensuring charm and uniqueness.brbrSleeps 6 Comfortably – Perfect for couples, families, or a group of friends.brbrIn-Unit Washer & Dryer – Convenience at your fingertips.brbrFully Equipped Kitchen – Stainless steel appliances, quartz countertops, farm sink, barn door pantry access, cookware, dishes, utensils, small appliances, and more.brbrPrivate Balcony – Sip your morning coffee or evening cocktail while watching palm trees sway in the breeze and boats pass by on the horizon.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

Welcome to Your Island Escape! Min 28-Day Reservation Required

Islamorada, Florida, United States

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$687.07

Latitude Adjustment, Islamorada, FloridabrThis 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.

Latitude Adjustment FLKeys

Islamorada, Florida, United States

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$340.29

Stunning Bay-View Townhome in Executive Bay Club – Newly Renovated!brbrDon't miss out on this rare gem! Perfectly located in the heart of Islamorada, this newly remodeled 3-bedroom, 3-bathroom townhome at Executive Bay Club offers the ideal escape to the Florida Keys. With two king beds and two twin beds, this spacious, bay-view unit comfortably accommodates families or groups, providing a tranquil retreat just steps from the water.brbrRelax and unwind on your private beach balcony while enjoying breathtaking sunsets over the bay – one of the few units in the neighborhood offering such a spectacular view. Whether you're, enjoying a nightly keys sunset, lounging at the private beach, or taking a dip in the pool, every corner of this home invites you to relax and recharge.brbrResort-style amenities include:brbrPrivate beach accessbrFreshwater poolbrTennis/pickleball courtsbrPlaygroundbrEnjoy the convenience of modern amenities, including air conditioning, high-speed WiFi, and an in-unit washer and dryer. The fully renovated interior features bright, stylish decor and all the comforts of home, making it the perfect place to unwind after a day of adventure.brbrSituated in the heart of Islamorada, you're just minutes away from top-rated restaurants, fishing charters, boutique shopping, and island attractions. Whether you're here for a romantic getaway or a family vacation, this townhome offers the perfect blend of luxury, relaxation, and convenience.brbrInstant book your stay today and experience the best of the Florida Keys!

BAY UNIT! 3-bedroom townhome in beautiful Islamorada with full amenities

Islamorada, Florida, United States

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$351.08

Indulge in the allure of the Florida Keys with our Caribbean retreat nestled in the heart of Islamorada. Immerse yourself in a 2-bedroom, 2-private bath with Queen beds comfortably accommodating up to 4 guests.brbrExperience the vibrant ambiance of our home through its beautiful Caribbean décor, open ceilings, and exquisite detailing, featuring solid wood doors, stone flooring, and an expansive living and dining area. Elevate your culinary adventures in the amazing chef-appointed kitchen equipped with Wolf appliances and a Subzero refrigerator.brbrLocated just across the street from The Caribbean Resort, revel in the luxury of full resort privileges, including access to a beach-entry pool and fishing pier. Dive into the tropical lifestyle with complimentary use of bicycles, kayaks, paddle boards, and fishing rods. Whether you’re indoors or outdoors, the authentic Caribbean atmosphere surrounds you.brbrYour comfort is our priority, with amenities like a washer-dryer, wireless Internet, and cable TV. Opt for the convenience of weekly housekeeping services. For those seeking to explore the waters, boat dockage is available for an additional fee, subject to space availability.brbrEscape to a Caribbean-inspired paradise, where every detail contributes to an unforgettable vacation experience in the Florida Keys.

Caribbean style home Islamorada - Oceanfront resort privileges.

Islamorada, Florida, United States

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$831.98

Direct OCEANFRONT home with HEATED POOL, BOAT DOCK for rent, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 bath p has endless views of the ocean from every room. If you enjoy watching the sun rise, this home also features 800 sq ft of decking to enjoy the ocean views while sipping your morning coffee. For your convenience, we also provide complimentary WiFi, flat screen TV’s, Netflix, Beach towels (as well as house towels), washer, dryer, dishwasher, hair dryers, beach chairs, two kayaks, games, and lots of information about where to eat/what to do.brbrThe resort contains a heated pool complete with outdoor bathrooms and lounge chairs overlooking the Atlantic Ocean. If the pools not for you, grab a beach chair & a life jacket and head down to one of the two beaches for kayaking and paddle boarding. If you’re bringing/renting a boat, we’ve got a boat slip available for rent - please inquire.The world-famous sandbar and snorkeling are only minutes away! There are so many things to do while at Anglers Reef, it is difficult to choose but we can help you decide!brbr123 Anglers Reef is the place to be – let us help you plan the vacation of your DREAMS!brbrPictures and description are representative of accommodations provided but are subject to change.brbr*** 2 Parking spots available***br***Boat dock available for rent - please inquire*** brNO PETS ALLOWED BY COMMUNITY LAWS

Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach

Islamorada, Florida, United States

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Bath

Sleeps

$912.01

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 to every place in town. brOur newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and a half bathrooms, to comfortably accommodate up to 6 adults plus children. The bright living area fully opens up to a private patio, where you'll love to gather by the heated plunge pool with a view of the sunset over the bay. brTruly in the heart of Islamorada, yet secluded within a protected cove among the mangroves. Less than a mile away from many of the best restaurants, bars and shops in town, including Lorelei, Morada Bay, Chef Michael's, Kaiyo Grill, Green Turtle Inn, Islamorada Beer Company, Florida Keys Brewery, Miss Monroe Boutique and Backcountry Cowboy. The Trading Post grocery store is located within 200 feet and open 365 days/year, 24 hours/day, and a fully-stocked Publix supermarket/pharmacy is a 3-minute drive away. Nearby marinas offer fishing charters, boat rentals, and much more. brOur development is located directly on the bay, with easy access to boat dockage, a community pool, and water sports. brPaddle boards and beach cruisers are available for your complimentary use. brbr*Golf cart rentals available at daily and weekly rates.*brbrOur community boat dock offers private slips for watercraft up to 35 feet in length. Please request a dock space upon booking your reservation. brbrAmenities include:br• Cleaning essentials - laundry detergent, dish soap & sponge, dishwasher detergent, multi-surface disinfectant spray, hand sanitizer br• Basic toiletries - plant-based shower gel, shampoo & conditionerbr• Blow dryer in each bathroombr• High-speed business internetbr• Smart UHD TVs in every bedroombr• Digital cable TVbr• Access to AppleTV, Netflix, Prime Video, Hulu, etc. br• Large-capacity washer and dryerbr• Fully-equipped kitchen with appliances - toaster, KitchenAid mixer, NutriBullet blender, Keurig coffee maker, Nespresso machine, Crockpot slow cooker, waffle maker, and morebr• Cooking, baking and serving utensils; pots, pans and trays; basic spice rackbr• Dinnerware, flatware, drinking glasses, coffee mugsbr• Weber propane gas grillbr• Private heated plunge poolbr• Townie/Electra beach cruisers (4 adult), adult tricycle (1), optional child’s bike seatbr• Paddle boards/paddles (3)br• Tesla chargerbrbrCome stay at our island paradise for a genuinely unforgettable Florida Keys vacation!brbrState of Florida DBPR license #: DWE5404408brIslamorada Vacation Rental RE#: 00399270-000400

Just relisted! Discounts on longer stays ~ Heart of Islamorada ~ Boat Dockage

Islamorada, Florida, United States

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Bath

Sleeps

$176.25

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 listing. Contact us for our available dates.brbr***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND AVAILABILITY FOR ALL SEASONS.***brbrI reply to EVERY inquiry. If you do not receive a prompt reply, please contact me again, and if you are having problems contacting us, please make sure that you put 28 days or more in the date range!brbrbrDive right into paradise while staying at Casa Rio. With a beautiful view from a raised master studio in the Florida Keys you can quickly relax and transform into 'island time.' This exclusive bayside home is situated in a secluded half acre location in Islamorada with quick access to the Florida Bay and Atlantic Ocean. Your master suite has its own private entrance and convenient on-site parking. Relax in the chikki hut while soaking in the beauty of the wide, private canal. Catch a glimpse of the elusive manatee grazing on the sea-grass as it swims by the dock. brConveniently located near Channel 2 and 5 bridges, you are within a quick 5 minute boat ride to the Atlantic Ocean. Go snorkeling or scuba diving in the amazingly clear waters of the Florida Keys at local reefs such as Alligator Lighthouse. Follow sea turtles and chase fish as you enjoy the lush reef life that make the Florida Keys so famous. Being in the 'Sportfishing Capital of the World' allows you access to many world renown fishing guides for excursions tailored to your linking in blue water and/or backcountry waters. brbrThe suite is fully furnished with a king sized bed, walk-in closet, shower and beach towels, refrigerator, microwave, coffee maker, blender, toaster oven, induction burner, slow cooker, flatware, dishware, and glassware. Also included is a 40” Smart TV, and free wifi. Enjoy your own patio with a gas BBQ just for your personal use. Your suite has central air and heat with your own controls. There is also a full bath with a separate shower and vanity area for your privacy. brA two person kayak, 2 bicycles, 2 beach chairs and 2 fishing poles are available for your pleasure, along with free dockage. Paddle boards available for rent. Bring your boat and keep it in the water while storing you trailer free of charge. Enjoy floating and snorkeling in the warm, crystal clear water of the private lagoon or travel to any of the local beaches just to bask in the sun. Islamorada restaurants are some of the finest in the Keys. You will find an extensive list of these excellent establishments for dining in or taking out preferences. brbrIf you are a restless traveler there are many tourist spots to visit during your stay. See wildlife and learn about the history of the area on a local eco tour. Visit Theater of the Sea or the Marathon Turtle Hospital. Enjoy fabulous sunsets from many of the local restaurants while sipping on the beverage of your choice. Boat rentals, day cruises, night cruises, parasailing, snorkeling, scuba diving, fishing and more are all available close by.brCasa Rio, is conveniently located midway between Miami and Key West. Closest airports are located in Ft. Lauderdale, Miami and Key West and shuttles are available to transport to and from.brSee us on Facebook - Casa Rio Islamorada

Apartment

Waterfront Paradise with Free Dockage - Contact us to price your stay!!

Islamorada, Florida, United States

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Bath

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$682.61

**JULY 4 HOLIDAY note: checkin & checkout dates are flexible between June 25th - July 11th - Min 7 nites. Enjoy the holiday at Anglers Reef 140!brbrANGLERSREEF140RENTAL is a uniquely designed 3 bedroom 2 1/2 bath home (the only home like it in Anglers Reef!). The HOME itself is TRULY OceanFRONT - not just one in an oceanfront community - with the BEST PANORAMIC, UNOBSTRUCTED OCEAN VIEWS. Check out the views in all of our photos and our guest reviews! Rental license 26-0297.brbr**Besides the best Ocean Views, you can enjoy another unique aspect of our home's location: QUIET!!br- Just steps away from the gorgeous POOL, but purposely NOT DIRECTLY ON IT, so NO POOL NOISE! br- FARTHEST AWAY FROM THE HIGHWAY, SO NO TRAFFIC NOISE!br- FARTHEST AWAY FROM HOG HEAVEN to the north, so NO LATE NIGHT MUSIC until midnight or later.br- Located on the southeast corner of the community, we have ONLY 2 ADJACENT ANGLERS SEASONAL NEIGHBORS, neither of whom rent.brbrThis 3 bedroom home includes BOTH a large dining area and a spacious living room in the original design -- all in an open floorplan -- not sacrificing one for the other as in some renovations here! brbrTHERE ARE SOME HOMES WITH OCEAN PEEKS OR PARTIAL VIEWS THRU THE TREES, BUT FOR PANORAMIC UNOBSTRUCTED OCEAN VIEWS - FROM INSIDE AND OUT - THERE IS ONLY ANGLERS REEF 140! See our many REVIEWS, which tell it all! Our home is known as Aqua Vistas and for good reason: THE OCEAN VIEWS DON'T GET ANY BETTER THAN FROM THIS HOME - inside from every room and outside from the two covered wraparound decks that offer OVER 700 SQFT of outdoor living areabrbrVIEWS: Although the Anglers Reef community is oceanfront, We are one of only 5 truly OceanFRONT HOMES in the community, and the only rental with our unobstructed ocean views. See the community layout in the photo gallery!brbrAND WE CAN OPTIONALLY PROVIDE A BOAT SLIP FOR YOUR STAY IF DESIRED (but if you don't need it, you won't have to pay for it!)brbrANGLER'S REEF is a boutique gated community of 52 homes inspired by Native Conch & British West Indies architecture with quaint streets & walking paths at Mile Marker 84.9 in Islamorada. With 3 bedrooms (including a King Master en suite, Queen guest bedroom and a 3rd bedroom with pyramid bunks (full down and twin up), 2 1/2 baths, plus a queen pullout sofa in the Living Room, Anglers Reef 140 accommodates up to 6 adults and 2 children..brbrRelax on one of our spacious decks, or in the lushly landscaped pool area with large heated and chilled pool, or on one of two stunning private beaches. Or take one of the provided kayaks or SUPs out for a paddle, visit a sandbar at low tide, or cast a line for great fishing! An optional boat slip is also available. We have direct ocean access via our deepwater channel, plus easy Gulf access via Snake Creek and Whale Harbor, both less than a mile away. brbrFishing in the Keys is known worldwide and Islamorada fishing locations don't get much better than this : br- the famous Islamorada Flats are right out front for bonefish, permit and tarpon; br- Alligator Reef is just a few miles offshore for snorkeling or feeding schools of the fish that hang around in this protected area. br- The inshore patch reefs just 1-3 miles away offer a variety of snappers and tasty bottom fish; br- and within just a few more miles off shore is the Islamorada Hump where there are sailfish, mahi, kingfish, wahoo, tuna and more along the big reef in a few hundred feet of water. brbrOur 31' boat slip in the Anglers boat lagoon is also available for your boat or a rental boat. Maximum allowed boat length is 31 feet, max draft is 3.5 feet and max height above the waterline of 9 feet. brbrWe are the original owners Anglers Ref140 since 2008 and have made many upgrades and additions nearly every year since for our - and YOUR - enjoyment! Our home is fully equipped with all the best - guests love the fully stocked kitchen and the propane BBQ grill on the deck - there's even an electric fireplace for cool winter evenings! And enjoying meals or cocktails while enjoying our ocean views -- from inside and out! The views don't stop when you go inside - the 7 pairs of French doors and numerous windows let you enjoy the panoramic ocean views from nearly every room. Watch sunrises from every bed! Tile showers, Viking and KitchenAid appliances, granite kitchen counters, 4 Flat Screen Smart TVs, & more! See link to our many GUEST REVIEWS! We are also the closest home to the south Beach for sunning and launching kayaks and SUPS, and just 150' from the heated and chilled pool (close enough for convenience, but far enough away to avoid the pool noise so you can enjoy a quiet afternoon or evening on your deck!)brbrPlease see our Availability Calendar for open weeks. We keep it very up to date with the exception of leases in process which do not show as booked until the lease and deposit are received. brbrFor Fishing People: PLEASE SEE OUR MANY GUEST REVIEWS for the best descriptions of what to expect at Anglers 140! Once you reserve your vacation with us, we will send you our Fishing Portfolio of our guests' catches, along with instructions so you or your kids to catch fish right in the Anglers boat lagoon! brbrIslamorada is synonymous with great fishing - gulf, backcountry or ocean. There are plenty of guides, charters, 'head boats' and boat rentals. You can also try for tarpon, permit, snook, spanish mackerel & more at nearby bridges or the many other nearby access points. Right at the Anglers property, we've caught mangrove snapper, redfish, ladyfish, jack crevalle, moonfish, grunts, mullet & barracuda depending on season - just bring a light rod or two (Basic fishing instructions at the house in our Welcome Book - detailed instructions will be emailed! Or send your questions and we'll try to answer!)brbrYou'll see the flats guides poling for bonefish and permit just off the Anglers Reef beaches! If you don't bring your own boat or charter with a guide, you can launch a kayak or SUP (after signing the Usage Agreement with your lease) from the beach, and try your luck fishing right out front or check out the mangrove shorelines (be careful of the strong tides by the bridges!) for snook, snappers, tarpon and barracuda! If you are serious about fishing from a kayak, bring or buy an inexpensive 3lb collapsible anchor and line!brbrFor Non-fishing People: One of the reasons we chose Anglers Reef is that both the development and the Islamorada area offer a lot to do for people who are NOT into fishing. Besides the gorgeous pool area in Anglers and great views from our decks and the private beaches, nearby is great shopping & restaurants (including 2 eateries you can walk to!), plus Founders Park, the Diving Museum, and of course Theater of the Sea just 1/2 mile away! And a new Publix is just a mile south for groceries!brbrOnsite: Enjoy our spacious wraparound decks with propane BBQ and the views of the turquoise waters; swim in the large pool (heated in winter and cooled in summer!), relax with a book or cocktail overlooking the Atlantic; take a quiet stroll thru the complex; or just catch some sun at the pool or on the private beaches. brbrRestaurants: Just a short walk north are Hog Heaven, a fun sports bar on the water with great happy hour and surprisingly good bar food. Next to it is Island Grill. Just north of the Snake Creek bridge is Puerto Vallarta, a very decent Mexican restaurant. A few miles south is upscale Pierre's on the Gulf and the more casual Morada Bay beach cafe and Islamorada Fishery (all next to Worldwide Sportsman for fishing tackle, clothing, and a large indoor aquarium); also a few more miles south you'll find the Green Turtle Inn, Lazy Days, and Square Grouper restaurants & many more eateries.brbrAttractions: Swim with dolphins at Theater of the Sea 1/2 mile south. Founders Park is just a mile north with concerts, pickleball, a bay bathing beach, and lots more. The Islamorada Chamber of Commerce visitors center is also near the entrance to Founders Park for local info as well as affordable postcards, posters, T-shirts and some booksabout the Keys.brbrShopping: So much so close! From upscale gifts and clothing to Keys-ey schtick and souvenirs. brbrGrocery & Other Shopping: A new Publix is just a mile south. There are also small markets in and around Islamorada, including the Trading Post two miles south. There is also a Winn Dixie a few minutes north (around Mile Marker 91 in Tavernier, west side of the highway). Buy your beer and wine at the grocery stores - less expensive than liquor stores. CVS is 1 mile south and also has well-priced beer/wine, some basic foodstuffs, some hats and clothing, and Keysy schtick.brbrIf you are going south, Marathon (about MM 50-ish) has a Publix, Winn Dixie, and a Home Depot.brbrFrom the north, at Florida City right where you get off onto Rt 1 is a BJ's Wholesale (membership required). There is also a Walmart there (but it seemed a little sketchy to us so we do not recommend it). Also check out Shell World in Key Largo for gifts and more!brbrOceanfront vacation, FLA Keys, boat slip, pool, oceanfront, waterfront, Fishing, Snorkeling, Scuba diving, Pickle ball, Anglers Reef,gated, Islamorada, weekly vacation rental, upscale keys vacation, tarpon, bonefish, kayak, sailfish, kayaking, beach, new, 3 bedrooms, ocean views, water views,

Truly OceanFRONT-BestPanoramicOceanViews-VLgDecks-QuietestLocation-AvailableSlip

Islamorada, Florida, United States

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Bath

Sleeps

$634.83

Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in living room, master and queen guest! Gourmet kitchen has granite countertops, stainless steel appliances and a great selection of cookware and utensils. Open floor plan with wet bar and formal dining room. Enjoy your morning coffee or afternoon cocktail with the gentle ocean breeze on the wonderful screened in water front balcony. This unit is the model for all of Bay Harbour and is professionally decorated and furnished.brbrThe condo includes all linens and is equipped with a full washer and dryer. Also included is the use of a 50-foot boat slip in a protected harbor with four-foot control depth. The large screened in balcony looks directly at your boat slip. There is immediate bay access and quick ocean access via Channel Two and Channel Five bridges. Fish cleaning stations, shore power and water are also on the slips. A marina is located across the harbor with gas, diesel and bait.brbrPrivate gated community with a large heated pool, jetted spa, two lighted tennis courts, clubhouse with fitness center. New stainless gas grills are conveniently located at the clubhouse for grilling your catch! brbrIslamorada is conveniently located 90 minutes from Miami and Key West. During your visit you can feed the tarpon at Robbie’s, enjoy a spectacular sunset at the Lorelei or swim with the dolphins at Theater of the Sea. brbrIslamorada is the “Sport Fishing Capital of the World”. Tarpon, bonefish, permit, mahi mahi, sailfish and sword fish abound in the tropical waters surrounding Islamorada. Flats fishing or blue water offshore fishing options are at your fingertips with Islamorada having the biggest fishing fleet in all of the Keys! At Bud n Mary’s you will find a great selection of deep-sea charters. Or if you prefer the backcountry, visit Worldwide Sportsman for a variety of different guides. brbrSo whether you want to fish, snorkel, dive or just sit by the pool and relax, this condo has something for you. br

Condo

Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym

Islamorada, Florida, United States

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Bath

Sleeps

$271.47

This lovely home has 2 bedrooms and 2 baths. The home is completely furnished, just bring you sunscreen, flip flops and fishing rods!brbrWhile here, you will have full access to all of the Islamorada resort amenities and activities. Including a heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.brbrIslamorada is the fishing capitol of the world, and you will easily find plenty of nice dining locally. Founders park is directly across the street for those that wish to walk over and have a day at the beach, or just play some pickle ball.brA min of 28 nights is required for these homes. Boat slips may be booked for an additional fee.

Wake up every day to the sunrise from the deck of this waterfront home 2bed home

Islamorada, Florida, United States

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Bath

Sleeps

$647.25

Welcome to Southern Comfort, your home away from home! Your ideal oceanfront getaway boasting 3 bedrooms and 4 baths and nestled along the coastline of Islamorada. brbrStep into your own private paradise, complete with a charming tiki hut where you can unwind with a refreshing drink or simply bask in the Florida Keys sun. The spacious pool area provides the perfect setting for leisurely swims or soaking up the sun while lounging on comfortable deck chairs.brbrInside, you'll find modern amenities and comfortable furnishings designed to enhance your stay. With well-appointed bedrooms, a fully equipped kitchen, and inviting living spaces, Southern Comfort ensures a seamless blend of comfort and convenience.brbrPerfectly located in Islamorada, it is a prime location for fishing and diving enthusiasts. With easy access to renowned fishing spots and vibrant coral reefs, you are minutes away from all kinds of water adventures! Explore the marine life Islamorada has to offer or embark on a fishing excursion to reel in the catch of the day.brbrWhether you're seeking a relaxing retreat or a base for coastal adventures, Southern Comfort promises an unforgettable vacation experience by the sea.

Experience luxury at Southern Comfort, a 3-bedroom oceanfront retreat in scenic Islamorada.

Islamorada, Florida, United States

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Bath

Sleeps

$355.03

Enjoy all the wonders Sandy Pointe Townhome has to offer. With breathtaking bay views, deep water dockage and a private beach, this townhome is the perfect Islamorada retreat. brbrThis bayfront home features 3 bedrooms and 2.5 bathrooms, townhome style. The main floor offers a fully equipped kitchen, open living and dining room with water views from every angle, and large balcony overlooking the beach. Located on the third floor is the three bedrooms, one with a queen bed, one with a tin bed and a full, and a luxurious master ensuite with stunning beach views. brbrReady for a beach day Or a day on the boat This unit offers the best of both worlds, with protected canal dockage and located only a few steps away from the beach. Sit and relax under the waterside tiki hut or take a dip in the bay. After a long day soaking up the sun and fishing, enjoy the sunset over the Florida Bay from your private balcony. brbrLocated on prestigious Lower Matecumbe, close to downtown Islamorada and only minutes away from the most wonderful fishing spots in the world. Enjoy backcountry fishing right in your backyard, or hop over to the oceanside via Channel 5 Bridge. brbr28 day minimum, please inquire for rates and availability. brbrDockage is available on a first come first serve basis. 30' max length. brbrSandy Pointe Townhome ~ MM74 Bayside

Bayfront Islamorada Townhome with Dock & Beach

Islamorada, Florida, United States

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Bath

Sleeps

$348.36

The perfect Islamorada getaway awaits. brbr Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, a private sandy beach and protected dockage, canal-side. brbrThis duplex features 3 bedrooms and 3 baths with an open layout for a spacious kitchen and dining room, and a living room with wall to wall sliding glass doors giving you unobstructed water views. Also on the main floor is two bedrooms, a comfortable master ensuite, and one guest room with a queen bed. Downstairs offers a separate one bedroom, one bathroom with two twin beds and a large carport with plenty of parking. brbr Spend the day in your backyard, at one of Islamorada's most pristine beaches, or load up the boat with fishing rods and explore all the wonders the Florida Keys waters have to offer. After a long day enjoying the Keys life, take a moment to sit back, relax and watch the sun set over the Florida Bay from your patio. brbrSandy Pointe is located on prestigious Lower Matecumbe, only miles away from downtown Islamorada and close to some of the best fishing spots in the world. Located only seconds away from the Everglades National Park and minutes from the ocean via Channel 5 bridge. brbr28 day minimum, please inquire for rates and availability. brbrDockage is available on a first come first serve basis. 30' max length. brbrSandy Pointe Villa ~ MM74 Bayside

Beachfront Islamorada Villa with Dockage

Islamorada, Florida, United States

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Bath

Sleeps

$306.81

Experience Islamorada like a local in this 3-bedroom condo. This superb property features 2 queen beds and 2 bunk beds, perfect for families or groups of friends. With amenities like WiFi, AC, and a washing machine, guests can relax and unwind in this peaceful retreat. The 2 bathrooms come equipped with a hairdryer and shower for added convenience. There is also an outdoor area- and a BBQ are also a plus. A great place to call homebase while you're away, we hope you enjoy your stay.

Condo

Charming 3-bedroom condo with WiFi and AC in delightful Islamorada

Islamorada, Florida, United States

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Bath

Sleeps

$436.07

This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full two-bedroom, two bath floor plan, has an upscale decor package and is fully furnished - just bring your suitcase. brbrWhile your experience will be private, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. heated pool, clubhouse, outdoor game lawn, billiards, and oceanfront tanning chairs on a boardwalk. A social calendar for all guests is always available for those who wish to be more social, while fine dining is only a minute's drive in Islamorada.brbrIslamorada is the fishing capital of the world, and you will easily find plenty of nice dining locally. Founders Park is directly across the street for those who wish to walk over for a day at the beach or play some pickleball.

Hotel Resort

Oceanview home in resort location!

Islamorada, Florida, United States

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Bath