Home Vacation Rentals By Owner In Islamorada, FL

Showing 580 Of 764 Vacation Rentals
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Exceptional(55)

$2241.97

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Private Vacation Home

Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks

Islamorada, Florida, United States

This is a brand new house. Just completed August 2014 brbrThis unique Gulf Front property is located among Gumbo Limbo, Mahogany, Royal Ponciana and palm trees sprinkled with other tropical foliage set directly on the Florida Bay/Gulf of Mexico. Hammocks and swings hang from the trees offering places to take frequent naps. The fabulous beach area and 60 ft. dock is an outdoor paradise. brbrThe dock is a boaters dream. It is fully protected from weather with deep water access. The property location is within direct view of Everglades National Park where back country fishing is world famous. Or possibly you would want to go deep sea fishing or scuba diving in the Atlantic Ocean just 15 minutes away through Snake Creek or Tavenier Creek. brbrThis estate is a three level home right on the water. The complete back of the house is windows allowing beautiful vistas and sunsets 24 /7. Appointed beautifully. High end appliances. Fireplace, shuffleboard table, ping pong table, swimming pool. Large porches. A perfect place for the discerning traveler. The electronics and TV's are state of the art. The master bedroom has a inferred sauna. brbrThe large gorgeous property is completely fenced in with a private electric gate adding security and peace. brbrKeywords: Florida Bay/Gulf of Mexico frontage, deep water with large dock, palm tree beach, sunsets, world famous fishing and diving, peaceful and charming setting. Ultra modern brand newly constructed estate.
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Bath 4

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Sleep 8

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Exceptional(95)

$313.39

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Villa

Keys Kottage & Bayside Villa W/ free onsite boat ramp marina & trailer parking.

Islamorada, Florida, United States

The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Kottage 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 ceiling. brbrThe property is directly on Florida Bay in the heart of Islamorada, and the Kottage is approximately 100 feet from the Bay. The Kottage is fully air-conditioned and has ceiling fans throughout. The bedrooms can accommodated up to 6 people and with the queen-size sofabed in the front room The appliances, and furniture are new.brbrWe provide pillows, sheets, blankets, and towels and all of your cooking and eating utensils. A washer and dryer are provided for your convenience.brbrA television and free wifi and secure internet are provided. Smoking is not permitted inside the Kottage.brbrThe property is beautiful, based in a native hardwood hammock, extending from US 1 to the bay. It has a protected boat basin which will accommodate boats up to 26 feet. There is a launching ramp for boats and a swimming area right off the property. Larger boats can be launched at one of several nearby ramps. Rental boats and fishing charters are available locally.brbrA boat ramp is available for boats up to 20 feet. Trailer parking is included for one boat trailer. Dockage for 1 boat 26 feet or less is also provided.brbrThere is parking for 2 cars. Founders Park, just a short drive north to Plantation Key is where you will find an olympic size pool, tennis, ball fields, dog park and other amenities.br. The nearby area has a multitude of restaurants, historic sites and nature preserves, shopping and many activities for children. Local shopping for clothing, souvenirs, and fishing and boating needs is plentiful. Grocery stores are convenient. There are several local attractions if you need a day out of the sun. Key West is an 80 minute drive away.brbrIslamorada is the Sportfishing Capital of the World. You're minutes away from the best back country (bonefish, tarpon, permit, snook, redfish), blue water (sailfish, dolphin, wahoo, cobia) and reef fishing (grouper, snapper, yellowtail) in the entire Florida Keys. There is quick access to the ocean-side both east and west around the key. Fishing off of our jetty in the evening is alot of fun for the kids. Magnificant snorkeling and scuba diving sites abound in the local area. A wide range of boating activities are available year round since our area of the bay is well protected. Kayaking, paddle boarding, and canoeing along our shoreline is popular. Nearby you will find Backcountry Cowboy Outfitters where you can rent kayaks, paddle boards,canoes, and bicycles. Of course water skiing and knee-boarding are a hit with the kids. brbrIn addition to the rare and tropical flora which abound on the property, the fauna which call the property home will entertain you during your stay. An osprey (called Ozzie by the locals) sits atop the trees in the area during the early evenings. We have an octopus in the marina who will look after your shrimp bucket if you leave it in the water. He may even play tug of war with you in the morning, and has been known to become a land animal when he is looking for a handout.brbrPete, the Great White Heron, frequently stations himself on the seawall. When you have had a successful day fishing he always seems to have gotten the message and is waiting for you upon your return to the dock. Watch your fillets carefully. If you get diverted, you will see how fast these creatures can move where food is concerned. His cousins, the pelicans, are usually right behind him when the fish cleaning begins and are just as brazen. And don’t be surprised if you walk out to the boat basin and find Izzie, the Iguana sunning himself .brbrThe Kottage is a unique place, and the people who visit, both owners and guests, feel very special about the property. The privacy is wonderful, the accommodations are new and clean, the property peaceful, and the access to the fishing is the best in the Keys, indisputably. We hope you will also find it as special as have we, and will add your name to the growing list who return to enjoy the most gorgeous sunsets and the best fishing and diving in the world.brbrThe Keys Kottage generally rents for 1 week intervals, from Saturday to Saturday. If the Keys Kottage is what you are looking for, please contact us and to reserve the dates. The reservation will be confirmed upon receiving a check for $500 of the total cost of the rental including tax.brbrWe look forward to your visiting our little piece of paradise, and are sure you will have a wonderful and special visit. If you have any questions, please feel free to call us at any time.brbrbrbrbrKeywords: Kottage
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Bath 2

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Exceptional(3)

$394.63

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Private Vacation Home

2BR/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access

Islamorada, Florida, United States

In the heart of the Florida Keys - Islamorada - an ancient reef awaits your arrival, where its waters brim with earth's most abundant marine life and it is nobly touted as "The Sport Fishing Capital of the World." Greeting you along its shore, native palms wave in a Caribbean breeze, framing dramatic ocean views where a spectacular pool meets the Atlantic. Preserved in the barefoot beauty of another time, Angler's Reef brings together quaint streets and walking paths to unite a community of homes crafted in the style of Native Conch and the British West Indies; Here private, deep water docks channel boats to the Mecca of fishing - famed Alligator Reef - just three miles to the south.brbrLocated in the center of the sport fishing and boating universe, Angler's Reef offers all the amenities of a classic-sport fishing resort, including:brbrGated entry for privacy and securitybr36 privately owned protected deep water docksbr500 feet of private beachfrontbrCrafted in the style of Key West Conch and the British West Indies: metal roof, spacious porch and classic gingerbread trimbrTile floors & morebrHeated Oceanfront pool with Mens & Womens BathhousebrClose proximity to several state and national parksbrNearby seafood restaurants serving the freshest catch of the daybrNearby Snake Creek Marina for water sports, fishing and boating servicesbrBoat trailer parking available along the Old Highway median outside the property gatebrAdditional auto parking available along the Old Highway median outside the property gate
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Bath 2

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Sleep 6

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Exceptional(1)

$1233.01

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Private Vacation Home

Stunning Bayfront Home with Pool & Dockage in Islamorada

Islamorada, Florida, United States

Grab a margarita and unwind at Marchettiville!brbrThis stunning 5-bedroom, 3-bathroom oceanfront property offers private breathtaking panoramic views of the Florida Bay.brbrLocated in Lower Matecumbe, it provides direct access to the Everglades and the Channel 5 bridge to the Atlantic Ocean. Just a few minutes drive to fine dining and shopping in downtown Islamorada.brbrThe upstairs boasts a spacious, open-concept living area with wall-to-wall hurricane-impact windows that frame the mesmerizing seascape. Enjoy the views from the gourmet kitchen and create chef-inspired meals with top-of-the-line appliances. brbrThe grand master includes an en-suite bathroom, ample closet space, and direct balcony access to the pool. The additional bedrooms are equally impressive, each with unique character and comfortable furnishings. brbrDownstairs is a spacious two-bedroom, one full bathroom, with it's own family room offering a comfortable separate space. brbrStep outside into your private oasis featuring a sparkling heated pool and a 30-foot beach area perfect for soaking up the sun. Light up the outdoor Fisher & Paykel grill and enjoy a freshly mixed frozen drink from the two restaurant-quality margarita-making machines. Relax in the spacious covered lounge area and take in the tranquil waters and sunsets at your own leisure.brbrSpend the day on the coastal waters - visit the well-known historic Alligator Lighthouse or grab a paddle board for a more active venture. brbrWhether you're spending the day on the water or recharging inside, we invite you to enjoy Marchettiville's serene ambiance and exclusive privacy.brbr28 night minimum. Please inquire for rates and availability. brbrMarchettiville ~ MM76 Bayside
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Bath 3

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Exceptional(3)

$1948.66

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Private Vacation Home

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

Islamorada, Florida, United States

Oceanfront luxury in the heart of Islamorada! This 5-bedroom retreat features lush tropical grounds, a private pool & private beach, boat basin, and dock with stunning ocean views. Enjoy sun-filled living spaces, a fully equipped kitchen, and easy access to fishing, snorkeling, and kayaking—your private slice of paradise in the Florida Keys. brbr - Oceanfront view br- Lush grounds for morning walksbr- High Speed Internetbr- Heated poolbr- Kayaks for guests usebr- Outdoor patio with BBQ grill br- 5 Bedrooms br- TVs with streaming services br- Private beachfront br- 2 designated workspaces br- Outdoor shower/rinse off area br- Many nearby restaurants brbr Escape to the heart of the Florida Keys at this breathtaking oceanfront retreat in Islamorada. Set on lush tropical grounds, this five-bedroom getaway offers the perfect blend of island charm and upscale comfort — ideal for families, couples, or groups seeking a serene escape by the sea.brbrWake up to endless turquoise views and spend your days relaxing by the sparkling private pool, soaking up the sun, or exploring the water from your own private dock and boat basin — perfect for fishing, snorkeling, or setting off on one of the kayaks. brbrInside, you’ll find spacious living areas bathed in natural light, a fully equipped kitchen for shared meals, and beautifully appointed bedrooms designed for rest and relaxation. Every window frames a glimpse of paradise — swaying palms, colorful blooms, and the tranquil ocean beyond.brbrAs evening falls, unwind under the stars with a cocktail in hand, listening to the gentle waves lapping against the shore. Whether you’re here for adventure or peace and quiet, this property offers a slice of true Keys magic.
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Bath 4

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Sleep 12

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$217.05

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Private Vacation Home

Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!

Islamorada, Florida, United States

Welcome to the Keys Life Cottage!brbrThis coastal inspired two-bedroom, one-bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned restaurants, breweries, marinas, and boutiques in the Florida Keys.brbrBetween the high vaulted tongue and groove ceilings, open floor plan, fully equipped kitchen, gorgeous bathroom, inside laundry, BBQ, cable and internet, it’s easy to make yourself right at home! The primary bedroom is equipped with a queen size bed, the second bedroom has a twin bed with trundle, and there is also a queen sleeper sofa in the living room for additional guests.brbrStep outside and enjoy the island breeze under your own private tiki hut, the perfect spot to relax with a drink, enjoy a meal, or simply unwind after a day of adventure. To make exploring even easier, two bicycles are included with your stay, ideal for cruising to the local breweries, boutiques, or grabbing a bite nearby.brbrAlso included in your stay is access to a private members-only club (only 1.5 miles away!) that offers a peaceful, secluded sanctuary complete with a heated and chilled pool, tiki bar, and tournament-rated fishing captains available for hire to take you out to experience the fantastic fishing Islamorada has to offer. Head out to the Everglades National Park and fish the flats for tarpon, snook, and bonefish, or head to the oceanside for the other fishing experience that brings avid anglers here year after year! For the other water experiences Islamorada has to offer that can’t be missed—snorkel tours, kayaks, paddle boards, and sandbar cruises—these can all be booked here as well. The club also has showers available and weekly events such as live music, painting nights, food trucks, and more.brbrThis home is your quintessential destination for island-style living. Come relax at the best-kept secret in the Keys. brbrHave any questions Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.brbrReservation Deposit & Cancellations: A reservation deposit equal to one-half (50%) of the total reservation amount is due at the time of booking. TENANT shall be entitled to a refund of the one-half (50%) reservation deposit, less any non-refundable fees, if the reservation is cancelled at least 60 days prior to the occupancy date. The remaining balance, including any required security deposit, is due no later than 60 days prior to the occupancy date. If the cancellation occurs within 60 days of the occupancy date, the full reservation amount shall be non-refundable. If the booking is made less than 60 days prior to the occupancy date, the full reservation amount shall be due at the time of booking, and TENANT shall not be entitled to a refund of any amounts paid in the event of cancellation. As an exception to the foregoing, TENANT shall be entitled to a refund of all amounts paid if COASTAL re-rents the property for the same amount and for the full rental period. If the property is re-rented for fewer days or at a lower rate, COASTAL may deduct from the refund the difference between the total amount due under TENANT’s original reservation (including all taxes and fees) and the amount received from the subsequent rental. brbrInstant quote prices and calendar availability are subject to change without notice and are not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.
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Bath 1

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Sleep 5

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Exceptional(2)

$2029.73

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Villa

Charming Ocean Front Pool Home with dockage & pool

Islamorada, Florida, United States

Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two living spaces, downstairs and upstairs. You will enjoy amazing ocean views from the 3rd floor-viewing porch. Enjoy a nice lunch out on the dock, which includes a round concrete picnic table. Midnight Runner has all the amenities for you and your guests to enjoy, at your private home away from it all!brbrKey Features of Midnight Runner:brbr- The Main Kitchen (Upstairs) includes all your usual appliances and tableware to feel at home. Downstairs has a Kitchenette area with a sink and mini fridge. brbr-Waterfront poolbrbr-Private Beachbrbr-Dock - 150-foot dock with 4'+ draft up to 50ft longbrbr-Enough parking for several vehicles/ trailersbrbr-No Petsbrbr-Minimum 7-day rentalbrbrVR LICENSE #24-1247brbr** Sargassum seaweed affects the coasts of the Florida Keys. Islamorada has its share, which ebbs and flows based on winds and tides, collecting on the shoreline at different times of the year. Sargassum is just another part of Nature’s rich tapestry. In the open ocean, this seaweed serves as a nursery ground and natural haven for sea life. It offers food, sanctuary, and breeding grounds for crabs, shrimp, whales, sea turtles, migratory birds, and over 120 fish species. SPRING AND SUMMER MONTHS are greatly affected, as this is not cleared out during this time period. **
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Bath 4

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Sleep 10

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Exceptional(6)

$2108.86

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Villa

Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater

Islamorada, Florida, United States

Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features an exotic wood deck surrounding a custom pool overlooking a private sugar sand beach on the Atlantic Ocean. Newly built-in outdoor shower! This home features an inviting living room with a sliding glass wall and a stunning 180-degree ocean view. You'll love to call Turtle Nest your home away from home. brbrKey Features of Turtle Nest: brbr-The kitchen includes all your usual appliances and tableware to feel at home brbr– Cinema media roombrbr- TVs in the living room and bedroomsbrbr- 150' Private beachbrbr- Viewing dockbrbr- Pool and spabrbr- 2 kayaks onsite for guest usebrbr- Enough parking for several vehicles and/or boat trailersbrbr- Minimum 7-day rentalbrbr- No PetsbrbrVR LICENSE #24-0363br** Sargassum seaweed affects the coasts of the Florida Keys. Islamorada has its share, which ebbs and flows based on winds and tides, collecting on the shoreline at different times of the year. Sargassum is just another part of Nature’s rich tapestry. In the open ocean, this seaweed serves as a nursery ground and natural haven for sea life. It offers food, sanctuary, and breeding grounds for crabs, shrimp, whales, sea turtles, migratory birds, and over 120 fish species. SPRING AND SUMMER MONTHS are greatly affected, as this is not cleared out during this time period. **
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Bath 4

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Sleep 12

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Exceptional(86)

$450.01

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Private Vacation Home

Anglers Reef Islamorada home with ocean views, private marina, beach & pool

Islamorada, Florida, United States

Angler's Retreat is a 2 bedroom, 2.5 bathroom single-family home with picturesque ocean views, privacy, and space. The property is in Angler's Reef, a boutique complex of 52 homes donned with quintessential Keys charm. Amenities include lavishly landscaped pathways, a serene, tropical community pool overlooking the Atlantic Ocean (heated in winter), 500 ft of private beach, and a marina with 36 boat slips with a deep water channel out to the Atlantic. Boat slips are available for rent (31' max). The house sleeps up to six comfortably and is appointed with delightful Keys motif, luxury touches, and amenities for the perfect Keys getaway. brbrEnjoy comfort and privacy with two bedrooms located on the 2nd floor, each with its own bathroom and spacious closet. Inside the master bedroom, you'll find a king-sized bed, cable television, dressers, and a private bathroom, including a glass-enclosed stand-up shower with a bench and granite double vanity. The master bedroom also has a walkout, ocean-view balcony with comfortable seating to enjoy the sunrise. The guest bedroom features two queen-sized beds, cable television, and abundant dresser space, and its private bathroom includes a shower with a full bathtub. For your convenience, each upstairs bathroom provides hair dryers and starter toiletries: shampoo, conditioner, bath gel, body lotion, and hand soap. Should you need an extra bed, the downstairs area includes two chairs that pull out to comfortable single sleepers. Additional pillows, bedding, and blankets can be found throughout the home.brbrDownstairs, ocean views off the porch make the perfect setting for morning coffee or 'anytime' cocktails (it is the Keys). The kitchen boasts stainless appliances, a refrigerator with an ice maker, a dishwasher, a stove, and granite counters, and looks into the living room, which includes an oversized couch for movie night on the 75 flat screen and smart TV. Of course, cable, including HBO, WiFi, and telephone, are included. The home is fully stocked with all your needs, so pack light. Items in the home include a coffee maker (Keurig and auto drip), blender, toaster, pots and pans, dishes, utensils, linens, bath towels, beach towels, iron, and even a collection of books and games. The home also has its washer-dryer in the hallway and a gas BBQ grill out back.brbrWe are located in Islamorada, the Sportfishing Capital of the World, just 90 minutes South of Miami. The area is known for its incredible wildlife, artisan shops and restaurants, and extensive waterways for boating, snorkeling, and scuba diving, most notably during the mini-lobster season. Explore by land or sea. You won't be disappointed.brbrWe are one of Islamorada’s limited licensed weekly vacation homes, VR-239.br
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Exceptional(15)

$324.81

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Condo

Gulf View Retreat @ Bay Harbor

Islamorada, Florida, United States

Summary:br2/2 Bay harbor condo with stunning Marina and Ocean views!brbrThe Space:brEscape to the breathtaking Gulf View Retreat in the highly coveted Bay Harbor community! Prepare to be enchanted by this hidden gem, nestled on the pristine shores of Lower Matecumbe Key in Islamorada, eagerly awaiting your arrival for your next unforgettable vacation. Discover the allure of Bay Harbor, a captivating four-building complex offering a wealth of amenities, including a shimmering community pool, tennis courts, an invigorating exercise room, and a marina. As a distinguished guest of this remarkable unit, you will enjoy exclusive access to an 18k boat lift, ensuring your cherished vessel remains secure throughout your stay. Please note that trailer storage is available offsite as it is not provided within the community. Embrace the prime location of this community, granting you seamless access to both the majestic ocean and the serene Florida Bay, perfect for indulging in all manner of boating adventures. Just moments away, you'll find the renowned Robbie's, an outdoor marketplace and restaurant, famed for its captivating Feed the Tarpon experience. We eagerly anticipate the honor of welcoming you to this extraordinary piece of paradise!brbrStep into this exquisitely appointed second-floor condo, where the allure of two beautifully adorned bedrooms and two bathrooms awaits you. Revel in the breathtaking views of the immaculate marina and the vast expanse of the ocean that grace every corner of this home. The master bedroom beckons with its generous walk-in closet, ensuite bathroom, luxuriously comfortable king-sized bed, and direct access to a private screened-in patio, where you can bask in the serenity of the surroundings. The guest bedroom is equally enticing, boasting its own private ensuite bathroom, as well as a queen-sized bed and a twin bed, ensuring a restful night's sleep for every guest. The fully equipped kitchen stands ready to cater to your culinary desires, providing all the essentials needed to craft a delicious home-cooked meal away from home.brbrWhen you step outside the front door, a world of adventure awaits at the marina, where in mere minutes, you can set sail to prime fishing grounds teeming with tarpon and other impressive trophy fish. For a change of pace, venture into the backcountry, where acclaimed snook fisheries await your skillful cast. Immerse yourself in the wonders of the nearby coral reefs, where divers can revel in the mesmerizing sight of graceful sea turtles gliding through the water, accompanied by vibrant schools of fish darting among the living corals, creating an unparalleled spectacle that epitomizes the very essence of the Keys.brbrGulf View Retreat offers you an invitation to a realm of tranquility and natural wonders, where stunning views, impeccable accommodations, and unmatched experiences converge. Allow yourself to be captivated by the allure of this coastal haven, where each moment is a testament to the extraordinary beauty of the surrounding landscapes. Your idyllic escape begins here, at Gulf View Retreat, where memories are made and dreams come to life. brbrbrThis home is managed by The Florida Keys Rental Store. For recommendations or things to do while in the keys, we have all the information you could need. Over 20 years in the business, we know what it takes to make your trip the best one yet!
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Sleep 4

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Exceptional(124)

$392.95

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Villa

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

Islamorada, Florida, United States

brThis beautiful villa is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84 and has access to one of the few privately owned boat slips. The homes boat slip is available for rent for an additional $350/week, paid after booking and gives you access to the deep water channel right in front of the community. The marina is capable of accommodating boats up to 31' in total length.brbrAngler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean. The detached villas are set along quaint streets and walking paths, where nothing is more than a few steps from your front door.brbrThe community amenities include a heated pool with outdoor bathrooms. Chaise lounge chairs and tables to sun and relax overlooking the beautiful blue waters of the Atlantic Ocean. There are two private beaches just a few short steps from every home that flank the marina and the privately owned boat slip which is available for rent. One beach has water access to launch a kayak or paddle board, which are provided, and the other beach is nestled among the protected mangroves where you can watch the gorgeous sunrise while sitting in an adirondack chair with your morning coffee. The lush landscape surrounds you with amazing palm trees, beautiful bougainvillea and some of the most colorful and gorgeous tropical foliage that only the Florida Keys can offer. The quiet gated community is ideal for families with kids of all ages as there is no road traffic. brbrBuilt in 2007, this villa is one of the larger exterior units and has 2 bedrooms located on the 2nd floor, both with private bathrooms. The 1st floor offers a wide open layout with a duel peninsula kitchen centered between dining and living rooms with french doors opening to the back patio. The house has many upgrades, such as stainless appliances, granite counters, rich hardwood floors, crown molding, 3 flat screen TVs, cable & WiFi.brThe Islamorada area is world famous for sport fishing and Angler's Reef has deep water boat docks perfectly poised for any aquatic excursion.brbr** Fully licensed by the Village of Islamorada for Vacation Rentals, license # 26-0183. brbrThe surrounding area has some of the best restaurants in the keys. Such as Lazy Days, Ziggie & Mad Dogs and Chef Michaels- just to name a few. The local watersports are endless and include all types of fishing from charters and boat rentals to jet skiing, paddle boarding, kayaking, and kite surfing.
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Bath 2

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Sleep 6

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Home Most popular vacation rentals in Islamorada