72,107 properties available

Located in Islamorada, Florida, United States. Ocean View Anglers Reef Villa - 150 - in Islamorada w/Optional On-Site Boat Slip Welcome to paradise! "Casa Dos Hondos II" is a bright, contemporary, single family, Key West style home located in the desirable waterfront gated resort community of Anglers Reef in Islamorada. The grounds and amenities are spectacular and feature a private heated pool on the coast of the Atlantic Ocean, two private beaches, and a private community marina (dedicated boat slip available upon request)...all less than a 50-yard stroll from our back porch down the palm tree-lined paths of Islamorada's premier vacation retreat.Casa Dos Hondos II features airy, high ceilings both upstairs and down, and an open layout on the first floor. The large kitchen was designed with gathering, cooking, and entertaining in mind! Quartz countertops, stainless steel appliances, and tile backsplash adorn the kitchen which opens into the living and dining areas at the back of the home. Two islands in the kitchen allow for extra

Located in Islamorada, Florida, United States. Anglers Reef Islamorada, Bikes,Kayak,Paddle Boards DOCK available-Pool 112 Anglers WayIslamorada Village vacation rental #24-0371Call me for more information 305-240-0592. (2 houses side by side available)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 bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat docks and views over the Atlantic Ocean that will take your breath away. Just minutes from many local shops, bars and restaurants. Access to the ocean does not get any easier than at Anglers Reef. When we first found Anglers Reef on vacation ten years ago we were sold and never went anywhere else. " The Yellow Tail House":There Are 52 Homes at Angler's Reef With Only 36 Boat Slips. Our home has the option for you to bring your own boat and use the dock (additional cost) . It is a Safe, Gated Community with very li

Located in Islamorada, Florida, United States. Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of stunning private beach. Protected deep water marina (slip available at additional cost) with a deep channel out to the Atlantic. Single and Tandem Kayaks as well as Stand Up Paddleboards available for your use. Launch kayak from the private beach and try your luck at Islamorada's famed bone fishing in the flats right out front. Brand new in 2008, this home is fully equipped. Tile showers, Stainless appliances, granite kitchen counters, 3 Flat Screen TVs, & more! Islamorada is the 'The Fishing Capital of the World' Great fishing in the gulf or ocean side. There are plenty of guides you can hook up with, as well as 'head boats' where you can walk on for a reasona

Located in Islamorada, Florida, United States. 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL Beautiful 4-bedroom, 3.5 bath home in Angler's Reef. Located at MM85, this tastefully decorated, open floor plan features a newly renovated gourmet kitchen including all of the amenities you’ll need for a perfect stay – updated appliances, quartz countertops and breakfast bar. Enjoy viewing some of the local artwork as you stroll throughout the home. We pride our home for hosting large groups and the newly added large sectional pulls out as additional sleeping space. A queen bedroom with en-suite bathroom is conveniently located on the first floor. There is also a stylish powder bathroom on the first floor off the kitchen and living area. The 8-person dining table is a perfect space to play cards and enjoy meals with your friends and family, while the kitchen island seats 5 people. A console table off the kitchen offers all the essential openers, koozies, martini shaker and plenty of games for a fun vacation! Th

Located in Tavernier, Florida, United States. Florida Keys 2 bed direct oceanfront. Seagulls Condo, 2 Bedrooms, 2 Baths, (Sleeps 4)This condo. offers the most spectacular, sweeping, direct ocean front views in all of the Florida Keys, featuring turquois colored waters. Our condo. is located in Tavenier, on Plantation Key, in the Village of Islamorada, at Mile Marker 90. This is an ideal location in the Upper Keys between Key Largo and the rest of the Village of Islamorada. It is easily accessible to numerous highly unique, locally owned and operated restaurants, markets, art galleries, fishing charters, boat rentals, snorkleing tours, museums, National, State, and local parks. Our location in the Florida Keys offers some of the most visually intense and stunningly beautiful views in the world. It is an hour and 1/2 drive to the Miami International Airport. It is an hour drive from the Everglades National Park, and a stunning and scenic 90 mile drive to the charming and ecclectic city of Key West at Mile Marker zero. ** 3

Located in Islamorada, Florida, United States. Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach Come stay at the Salty Pelican in Angler's Reef! This magnificent home with amazing direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Home also overlooks the community pool. Anglers Reef is a quiet oceanfront community in the Florida Keys. Angler's Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home's boat slip is available for rent with a deep channel out to the Atlantic ($500 per week. Let owner know after booking to add dock). Or launch your kayak from the private beach (kayak rentals available for drop-off). Built in 2007, this home has 2 bedrooms located on the 2nd floor, the master

Located in Tavernier, Florida, United States. Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly Welcome to Islamorada- the Fishing Capital of the World.Oceanfront living doesn't get better than this. In the heart of Islamorada, this vacation home is located on the exclusive Millionaire's Row. Once you enter into the private oceanfront estate, you have arrived in paradise! The house has two levels which are accessed via the outside staircase. The first floor boasts two bedrooms. The first bedroom features a king bed, a twin bed, TV, and a small refrigerator. The second bedroom has two full beds, and a TV. Both bedrooms share a large bathroom.The main floor is upstairs where you will find the living room, dining room, kitchen, laundry room, and sun room with spectacular ocean views. Also upstairs is a master bedroom with a king bed, TV, and en suite bathroom. The second bedroom has two full size beds and a TV. There is a hall bathroom as well.Relax by the amazing heated pool overlooking the Atlantic Ocean

Located in Tavernier, Florida, United States. Islamorada Oasis, Luxury open concept private home. Islamorada Oasis is designed for families and outdoor lovers! Inside and out, its ready for entertaining and keys style relaxation. Includes separate studio downstairs that is perfect for grandparents. Huge beautiful canal front with optional 20,000 pound boat lift that can accommodate 30 foot vessel. Ice machine makes 300 pounds over per day, great for keeping the catch cold and fresh. Cool off in the saltwater pool that’s large enough to do laps! Huge outdoor grilling and entertainment area overlooking the water.

Located in Islamorada, Florida, United States. 3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach Your own tropical paradise overlooking the fabulous Florida Bay - this family favorite is just 67 miles south of Miami! Futura Yacht Club is a small, gated community with a private marina and accommodations available for that tranquil tropical getaway you've always imagined. This is an elegant 5th floor 3 bedroom, 2 bath condo large enough for a party of 7, but still stylish, comfortable and affordable. This condo has a private balcony and is located in the tower bldg, just a short elevator ride away from the tennis courts and swimming pool. This condo comes fully equipped with all your vacation comforts in mind. Wireless internet available. Protected dockage is available for boats up to 36 feet with easy ocean access through Snake Creek or Tavernier Creek for just $200 per week. $250 per week during holiday weeks. If you need a slip, please request when booking and we will adjust your quote. No charge for trailer stor

Located in Islamorada, Florida, United States. 2BR/2.5BA Angler's Reef Cottage 116 With Private Beach and Pool Access Check out our video tour! All NEW Anglers Reef Villa 116, a modern beach retreat offering relaxation at its finest. Our Villa is perfect for families or couples seeking to make the best of their Florida Keys vacation. Enjoy a fresh cup of coffee each morning on the Patio or and take in the fresh seaside air. Cook meals with ease in the open and fully stocked kitchen. Anglers Reef offers a nearby grocery store, convenience stores, and many restaurants, diving and snorkeling trip locations, kayaking, and so much more. Guests at Angler's Reef have exclusive access to 500' of private beachfront as well as an oceanfront swimming pool!No more than two vehicles are permitted per residence. This home does not include dockage. We suggest Snake Creek Marina located less than a quarter-mile south for slip space, trailer storage, and launching your boat. Additional costs apply.

Located in Islamorada, Florida, United States. Angler's reef 2024 SUMMER SPECIAL RATES- 2 bedroom beautiful house Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located in an exclusive gated community of 50 island homes called Angler's Reef. The community includes a beautiful oceanfront pool, a private marina, and two stunning man-made beaches, a rarity in the Florida Keys. A famous sandbar amid turquoise waters is located right in front of the community and can be reached by kayak or boat.Our island home is cleaned professionally and we maintain a non-smoking pet-free environment. The house sleeps four and has a Master bedroom with an en-suite Master bathroom and a large private balcony. The large second bedroom is also a master suite featuring an en-suite bathroom with a tub and a small private balcony. The living area includes a formal dining room and living room, as well as a modern open kitchen. A large sofa can accommodate one or two children if more sleeping spa

Located in Islamorada, Florida, United States. Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach *****New Owners/Listing so you may not see reviews yet for that reason*********** Please email and I will answer any questions you have!*****Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 bath home 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.The 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 kaya

Located in Islamorada, Florida, United States. Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 Pineapple Beach is situated on more than 3 acres in the central area of Islamorada. This exclusive 5-bedroom luxury residence is the embodiment of your dreams, offering nightly bonfires, a challenging putting green, a cabana bar, a private dock, and numerous other amenities. Get ready to pack your bags and experience a vacation that will leave an indelible mark! If you've ever envisioned lounging by your own private oceanfront pool, gazing over a pristine white sandy beach and crystal-clear waters, your dream is about to come true!This exquisite estate boasts a gourmet kitchen and a dining area that accommodates 10 guests, offering breathtaking water views. With three levels, there's ample space for you and your guests to spread out. Unwind in the living room, where a 65” TV awaits your movie nights, or engage in a friendly foosball game. Outdoors, indulge in your private beach, complete with a fire pit, boat dock, pool wi

Located in Islamorada, Florida, United States. Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat ramp and parking (for an additional charge). A heated pool with panoramic Ocean Views and lawn games on the terrace makes it the perfect place to soak up some sun. Guests enjoy a daily continental breakfast, complimentary self-parking, bike rentals, stand-up paddle boards, kayaks, and outdoor barbecue facilities. PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 50 /night/unit (plus taxes) on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 years old;We're

Located in Islamorada, Florida, United States. Tranquil One Bedroom Cottage with Pool and Boat Basin Hawksbill Cottage - The Hawksbill Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their 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 peaceful bungalow is secluded in lush tropical landscaping. It features a king bedroom, bathroom with walk-in shower, kitchen, living room and private patio. The decor and furnishings give it a tranquil feel. The Hawksbill Cottage can be rented separately or in combination with any of the other four homes. There is a cottage above the attached garage, referred to as The Treehouse, that is convenient to rent for family and friends.VACATION RENTAL LICENSE: 24-0416 If booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on an annua

Located in Islamorada, Florida, United States. Your Islamorada Vacation dream just became a reality!  139 Venetian Way - Your Islamorada Winter Vacation dream just became a reality! Brand new to the market, this Venetian Shores Pool home is waiting for you! This amazing four-bedroom home was recently purchased, professionally painted, and beautifully furnished! What more could you ask for? 139 Venetian Way is located on the bayside at Mile Marker 86 on a plugged canal close to groceries, dining, fresh fish, and frozen margaritas! If booking more than a year in advance current prices may not reflect the 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 Vacations. You will also see a charge from V

Located in Tavernier, Florida, United States. Charming 1 Bedroom Condo on Plantation Key Sit back and relax at Port o Palms. Experience the ultimate Florida Keys getaway at this light and bright one-bedroom, one-bathroom condo nestled within the serene Port O Palms community. The spacious screened-in porch offers a great spot to relax and soak up the surroundings. Enjoy the convenience of the community amenities, including a refreshing pool, multiple tiki huts for shade and relaxation, and dockage for boaters. The inclusion of WiFi and television ensures that you can stay connected or unwind after a day living the Keys life. The condo comes with one covered parking space, community BBQ grills, an ice machine, and is fully gated for ultimate privacy. The quaint community of Port O Palms provides a serene atmosphere for you to enjoy from sunrise to sunset.The convenient location on Plantation Key, close to restaurants, grocery stores, shopping, and more, makes it easy for you to explore the area and enjoy local favorites like Mar B

Located in Islamorada, Florida, United States. Venetian Shores 20K boat lift 28 day Minimum, ..August Cancellation now open.... Venetian shores 4 bedroom 3 bath, pool, hotub, 300lbs ice machine with 20K boat lift, Master has a double walk-in shower, separate 1 bedroom with full bath on lower unit great for privacy, full kitchen with al stainless appliances

Located in Tavernier, Florida, United States. Casa Margarita Islamorada, Paradise awaits!! Experience Islamorada like a local in this 3-bedroom 3-bath pool home. This beautiful recently remodeled 3 bed 3 bath pool home on canal with bay and ocean access, property offers a superb stay for guests, with its cozy bedrooms featuring a king bed, a full bed, and a queen bed. The house is equipped with all the essentials you need, including a hair dryer, iron, washing machine, AC, WiFi, and heating. The 3 bathrooms are complete with showers and hair dryers. Kickback, relax, and enjoy everything Islamorada and our house has to offer.property is on a 60' wide canal with concrete dock to fit up to 28' boat

Located in Islamorada, Florida, United States. Relax in this gorgeous townhome while overlooking the sparkling Atlantic Ocean Windy Cove #2 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features three bedrooms and two bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the beach under a palm tree, or wake up early to catch a sunrise from your own balcony overlooking the water. 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.

Located in Tavernier, Florida, United States. 5 Bedroom / 4 Bath Relaxed Plantation Key Resort Style Home with Pool & Dockage Greetings from Captain's Quarters! Located on Plantation Key (Mile Marker 90), this beautifully updated five bedroom and four bathroom canal-front home offers a resort-like experience.The main living area, located on the second floor, includes three bedrooms, two full bathrooms, comfortable open living space with a fully equipped kitchen. Guests can enjoy their meals while taking in the beautiful views from the screened porch, which overlooks a tranquil cove across the wide canal. On the lower level, there are two private suites, one apartment includes a queen bedroom and a full bathroom, while the other offers another queen size bed, pull-out sofa bed, bathroom, and a kitchenette. Outside, guests can relax and unwind in the fenced and gated turf yard, which features a spacious pool with a heater/chiller. The dock area includes a 15,000 lb boat lift, a floating dock for kayaks, and a built-in outdoor kitche

Located in Islamorada, Florida, United States. Beautiful Townhouse in the heart of the Florida Keys SNOW BIRD.. COME TO PARADISE. 2/2 with a Loft (can be a 3rd bedroom) beautifully located in the heart of the Florida Keys. Amazing sunset, great community pool and beach. Next to founders park with many amenities that can be used when staying at this home away from home. Boat access, slips and marina. Great pier for fishing and watching the best sunsets in the keys. Great family atmosphere with so many amazing restaurants to choose from. Ask owner for suggestions.

Located in Islamorada, Florida, United States. Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of Islamorada. Located within a gated community with 24 hr. security. Includes fully equipped kitchen w/ granite countertops, microwave and s/s appliances; With washer & dryer, plasma TV, electric outdoor grill, cable, and phone. Sleeps up to 8 - oversized master bedroom w/ one king bed, TV, walk-in closet and loft access with 2 twin beds. Second bedroom includes 2 double beds & balcony. Two pack-n-plays, baby tub, and portable high chair available. Outdoor sitting area/patio and private beach,pool, 2 tennis courts, clubhouse, playground, and bbq grill within community grounds. Enjoy FL Keys sunsets as you fish from pier or sip on your favorite cocktail. Boat ramp and marina available next door at Founder's park or nearby marinas for your convenience.

Located in Islamorada, Florida, United States. Lush tropical plantings in a gated compound located directly on the Florida Bay PROPERTY NAME: Little Bay Cottage82246 Overseas Highway, Islamorada, FloridaLOCATION: Cottage located directly on the Florida BayMINIMUM STAY: Weekly or MonthlyMILE MARKER: 82.2DETAILS: - Located on a one-acre lush tropical setting in a gated compound directly on Florida Bay- One of 3 separate units for rent by the week or month, each sleeping up to 6 people- Protected dockage for up to a 34-foot boat- Sunning area with lounge chairs on the peninsula- Hammocks, pergola, and tiki for relaxing- Panoramic views of Florida Bay from the covered balcony- Spacious interior with 2 bedrooms, 2 bathrooms, and a queen-size sleeper sofa- Updated kitchen with new appliances and granite countertopsLittle Bay's Cottage is a ground-floor home with a unique floor plan. The main living area is in the center of the house, with a kitchen, dining area, sitting area, and full bathroom. To the right is a large bedroom with a kin