Vacation Condo Rentals By Owner In Islamorada, FL

Come, Enjoy and Relax in our beautiful piece of the paradise in the Florida Keys. The Executive Bay Club is located in Islamorada, the Diving/Snorkeling and Sport Fishing Capital of the world! This is a private, gated community with 24 hour security and easy accessible parking. The grounds have 2 tennis courts, heated swimming pool, club house, private beach and fishing dock. brbrOur two story unit has been renovated. The master bedroom has a king size bed, a renovated bathroom is adjacent. The second bedroom has 2 queen size beds and its own newly renovated bathroom television and DVD player. Downstairs relax in our living room, that sports a big screen TV or enjoy the quite patio right outside. There is also a dining area, kitchen with full size dishwasher, microwave, refrigerator and washer and dryer and an additional renovated bathroom with shower. The unit is fully furnished and we provide cooking utensils, dishes, linens and towels. However, bring you own pool/beach towels.brbrNext door is Founders Park, known to be one of the Keys most beautiful parks, with baseball, soccer fields, exercise equipment, basketball courts, tennis courts and pros available for tennis drills, lessons and round robins, private beach and playground, boat marina and public boat ramp. Let's not to forget the heated Olympic size pool with diving and lap areas, where swim lessons are available. Minutes away are your charter boats and captains, your scuba and snorkeling trips and wind sailing lessons. Our water is clear and our reefs are impressive! Don't forget to stop by the local art galleries, 'Theater of the Sea', a Marine Adventure where you can swim with the dolphins or drop by the Diving Museum. The activities are plentiful... water sports, kayaking, jet skis, parasailing, boating, sunset cruises and just reading and relaxing on the beach! The restaurants are the best in the Keys with local fish served daily. brbrSorry No Pets or Nor SmokingbrbrSo come, relax and Enjoy whatever your pleasure may be!brbr

Islamorada Spectacular Vacation At Executive Bay Club

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2748.36

This oceanfront villa at The Islands of Islamorada, a private, gated oceanfront resort in the Florida Keys, is designed for the way families actually vacation, with unobstructed Atlantic views from every level.brbrAcross three stories and more than 3,100 square feet, the home offers space to spread out without sacrificing comfort or style. Three en-suite king bedrooms serve the adults, while a dedicated bunk room gives the kids a space to call their own. A full kitchen, dining room, and ground-floor loggia create the relaxed, at-home atmosphere that turns a stay into something more. Private balconies, a laundry room, and a two-car garage complete the experience, with select villas also featuring private elevator access.brbrBeyond the villa, enjoy access to a full suite of resort-style amenities designed for both relaxation and activity. Spend your days between two swimming pools and a jacuzzi, unwind at the oceanfront bar or around the fire pits, or take advantage of paddleboards, kayaks, and Hobie Cat sailing, all just steps from your villa. Guests also have access to a fitness center, yoga classes, pickleball courts, a playground, and grill stations, along with 24-hour on-site assistance and property-wide high-speed internet.

Oceanfront 4BR Villa | Resort Access + Bunks

Islamorada, Florida, United States

Bed

Bath

Sleeps

$231.64

Watch the sunrise from your private balconies in both bedrooms overlooking the Atlantic ocean, and walk across the street to amazing sunsets on the Gulf of Mexico in Founder's Park or Marker 88 Restaurant. brbrEnjoy the fully renovated condo with wood floors, marble in both bathrooms, granite countertops, a 55 TV in the living room, high-speed WiFi, and reclaimed wood bar. The kitchen has all the equipment and utensils you need to make a great meal, and a community BBQ is located just below the unit by the water. Clean up is easy with a in-unit dishwasher, washer and dryer.brbrWe are located an hour south of Miami and you will be less than two hours north of Key West - a perfect day trip. Islamorada is the fishing capital of the world, with charter captains available to take you on the water on your whim.brbrThe property has a small exercise room (run or walk on the treadmill while looking at the ocean waves!), a lovely heated pool with lots of loungers and rockers, a beautiful dock and a community BBQ to grill your catch on.brbrWe have a small, friendly, community of 80 units, and are looking forward to hosting great people. Please reach out today so we can discuss your Keys dreams.

Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$376.16

Experience the ultimate Florida Keys getaway at Ocean Harbour M-42, a beautifully appointed 3-bedroom, 2-bath ocean view condo tucked inside one of Islamorada's most sought-after gated communities. Protected dockage in the marina. The unit has a 30' boat slip included.brbrWake up to sparkling ocean views from the spacious master suite, complete with a king bed, private balcony access, and an en-suite bath featuring dual vanities and a walk-in shower. Two comfortable guest bedrooms provide plenty of space for family or friends — one with a king bed and the other has a day bed with a trundle— all styled in soothing coastal tones that reflect the laid-back island vibe.brbrThe open-concept living area is bright and inviting, with large sliding glass doors that frame the endless blue of the Atlantic. A fully equipped kitchen with stainless steel appliances and granite countertops makes meal prep a breeze, and the private balcony is the perfect spot for morning coffee or sunset cocktails.brbrGuests at Ocean Harbour enjoy resort-style amenities including:brbrA stunning oceanfront pool and hot tubbrbrMarina with boat slips brbrLighted tennis and pickleball courtsbrbrFitness center and clubhousebrbrPrivate sandy beach and tiki huts for relaxing in the shadebrbrLocated in the heart of Islamorada, you'll be close to world-class fishing, snorkeling, waterfront dining, and boutique shopping — everything that makes the Keys so special.brbrWhether you're looking for a relaxing escape or an adventure on the water, Ocean Harbour M-42 is the perfect place to experience island living at its best.

Charming 3BR condo in Islamorada with heated pool and gorgeous ocean views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$404.61

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. brbrThis unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, tennis courts, gas barbeque grills, tennis equipment, beach chairs and coolers.brbrThis spectacular condo offers two master bedrooms with private full bathrooms, additional half bath and full size washer and dryer. Additionally, each bedroom and the living room has flat screen televisions with cable tv. A dvd player is included in the living room. There is free wifi and telephone included for your use. The kitchen has stainless steel appliances, granite countertops and everything you need to prepare and serve a gourmet meal. brbrThe large balcony overlooking the water offers plenty of seating. Enjoy a meal or coffee while you take in the expansive views or enjoy the sunrise. Additionally, you will have a direct view of your boat parked in a private boat slip just steps away. brbrLocated at mile marker 75, this boater’s paradise is just minutes from fishing in the gulf or ocean, diving or snorkeling beautiful reefs, jet skiing, parasailing, kiteboarding or kayaking. brbrCall us to book your vacation of a lifetime.br

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada, Florida, United States

Bed

Bath

Sleeps

$257.63

August to November, take $500 off regular price! World Famous Beacon Reef Condo (a gated community) Oceanfront Islamorada, Florida (Max 4 Persons /monthly rentals only!!) Come and enjoy our 2nd home in Paradise! FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world, Islamorada. Conveniently located, walk to local restaurants. Come into our beautifully furnished 2 BR 2 BA Condo on the second floor.(First is parking only) Convenient Staircase from back porch directly down to grounds. Only units on this floor have the convenience of using private stairs to grounds others have to use the lobby and elevator. The master bedroom and outside patio gives a beautiful view of the OCEAN. Wake up to the sunrise. Inside find a fully equipped kitchen with extras as is ou 2nd home, An inside washer/dryer. Games, books, comfortable furniture, and smart TVs throughout. Tile floors for easy care. Go out into the mild weather & wander among our beautiful tropical gardens, bring your drink down to the waters edge or curl up with a good book. Sandy BEACH boasts lounge chairs under Tiki huts and wonderful chaise lounges and tables around the pool. Fish or swim from the beautiful newly rebuilt T-dock with electric and water at each slip and ice machines on the dock. A big cleaning station for your fresh catch. Most restaurants will cook it for you. Or just hang out and watch the fishermen come in. Don’t forget to Bring your boat or rent one at the numerous places nearby, FREE DOCKAGE! Water and electric included at each slip.brbrDon't miss the state of the art work out room equipped with an inferred SAUNA, so after a vigorous workout or a day on the water, relax and get rejuvenated in the therapeutic SAUNA and relieve any aches in the hot tub.brbrSwim in our heated fresh water pool with zero entry or lounge in our huge therapeutic Jacuzzi. Have a party under the thatched Tiki roofed 'room', can be open air, or clear plastic curtains roll down to keep the wind and weather out. It is fully equipped with ice machine, fridge, sink, grills, a smoker, tables, chairs and benches and a serving bar with a sink, ice machine and refrigerator.! A paradise you will want to come back to again and again. Play cards or eat with friends. Spontaneous parties have been known to erupt as one of the many grills lights up!brbrKeywords: Beacon Reef, Condo, Islamorada, fishing, oceanfront, sandy beach, boating, swimming, pool, beach front, ocean front

BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL SUMMER DEAL

Islamorada, Florida, United States

Bed

Bath

Sleeps

$726.22

Oceanview Maison Matecumbe #306 - Maison Matecumbe is an exclusive gated and private boutique townhome complex. This wonderful unit offers an open floor and three inviting bedrooms and three baths. The master en suite has a king bed, second guest room has two full beds, and the lower-level guest room has a queen bed. Newly renovated kitchen opens up to the dining and living room. The patio offers beautiful ocean views. Lounge by the newly renovated tropically landscaped pool, or on a hammock on the white sandy beach overlooking the Atlantic. Outside oceanfront kitchen, tiki hut and hot tub. Centrally located close to great restaurants, marinas, cafes and boutiques. brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brVACATION RENTAL LICENSE: VR-124 brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Oceanview 3-bedroom condo in Islamorada with ocean views, perfect for 6 guests!

Islamorada, Florida, United States

3

Bed

3

Bath

6

Sleeps

$545.63

Welcome to Pressure Drop! brbrThis beautiful ocean-view condo features three bedrooms and two full bathrooms, making it an ideal choice for families or groups of friends. Modern amenities and coastal decor throughout create a cozy, welcoming environment for your stay. The spacious living room showcases stunning ocean views and opens to a large screened-in balcony, perfect for enjoying sunrises or feeling the salty breeze. The fully equipped kitchen includes additional features like an office nook and bar seating. The master bedroom offers a king-sized bed and a private bathroom complete with a walk-in shower, jetted tub, double vanity sinks, and a water closet. The second and third bedrooms are furnished with queen beds, sharing a full bathroom. Additional conveniences include a washer and dryer, central air conditioning, streaming TV’s, and high-speed internet throughout the condo.br brSituated in the desirable Bay Harbour community on Lower Matecumbe Key, this resort-style community offers amenities such as a pool, jacuzzi, fitness center, and tennis and pickleball courts. Anglers will appreciate boat slips that can be reserved for an additional fee (must be reserved in advance). With direct access to Florida Bay, you can easily venture out to Everglades National Park to fish for snook, redfish, bonefish, and permit, or take a short trip to the ocean for sailfish, mahi-mahi, snapper, wahoo, and more! The famous Islamorada sandbar is nearby, offering crystal-clear waters and a laid-back atmosphere. During spring and summer, try your luck at Channel 2 or Channel 5 bridge for the renowned “Silver Kings” (tarpon) for an exhilarating catch. While there is no trailer parking on-site, Seabird Marina offers options for trailer parking.br brAt the top of the neighborhood, you'll find a local seafood market with fresh lobster, fish, shrimp, and more. Just 1.5 miles south is Anne’s Beach, a hidden gem featuring a winding boardwalk through mangroves and sheltered picnic areas where you can enjoy lunch while taking in the ocean views. Anne’s Beach is also popular with windsurfers, and on breezy days, it’s entertaining to watch them glide across the water. The expansive shallow areas make wading and enjoying the warm, turquoise waters a delightful year-round activity.br brIslamorada, located in the heart of the Florida Keys, offers a prime vacation destination. Whether you enjoy deep-sea fishing, exploring backcountry shallows, diving or snorkeling vibrant reefs, sailing, kayaking, parasailing, or windsurfing, there’s something for everyone. Just five minutes north is the famous Robbies, where you can find fishing and snorkeling charters, a restaurant and bar, shops, and rentals for parasailing, kayaks, and paddleboards. You can even hand-feed the massive tarpon! Habanos is another local favorite, offering oceanfront dining and classic Cuban cuisine. Downtown Islamorada is only ten minutes north, featuring a variety of restaurants, breweries, shops, activities, and grocery stores. Key West is a scenic 1.5-hour drive to the south.brbrTake advantage of a local’s secret and park your vehicle and utilize the Islamorada Freebee; Our local rideshare service offering door-to-door transportation service to and from your favorite Islamorada destinations with environmentally friendly electric vehicles. It’s not only a fun alternative transportation option – it reduces traffic congestion, addresses drinking and driving, and reduces the Village’s carbon footprint. Two Tesla Model X vehicles can accommodate up to seven passengers and one larger vehicle that can accommodate a wheelchair and up to nine passengers. 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.brbrIslamorada Vacation Rental License: 26-5029

Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$357.53

Sleeps 4, 1 Bedroom - King Bed, 2 Full Bathrooms, Queen Sleeper Sofa, 2 TVs, Balcony, fully stocked kitchen, towels & linens provided, coin laundry available, elevators. Newly remodeled unit. Assigned, Covered Parking. Gated Community. Men’s & Women’s Fitness Centers, Club House, Pool & Jacuzzi, Ocean Front, Boat Ramp, Steps in to ocean. Great for Paddleboard & Kayaking. Walking distance to several restaurants. Minutes from several marinas. Best scuba diving & deep sea fishing in Keys!brbrKayak available to our guests. brbrMarina located just next door.

Ocean & Bay Views. Welcome To Paradise!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1180.83

Welcome to Maison 402 Island Charm, your perfect vacation retreat in the heart of Islamorada! This charming 3-bedroom, 3.5-bathroom townhome offers a blend of comfort, luxury, and convenience, making it the ideal home away from home.brbrNestled in a prime location with breathtaking ocean views, Maison 402 Island Charm provides easy access to an array of restaurants and shopping destinations in downtown Islamorada. Whether you're a foodie eager to explore local cuisine or a shopper looking for unique finds, you'll be just steps away from the best that Islamorada has to offer.brbrAs you step inside, you'll be greeted by an open-concept living area that features coastal decor and ample seating. The fully equipped kitchen, complete with modern appliances and generous counter space, is perfect for preparing delicious meals for family and friends.brbrEach of the three cozy bedrooms is thoughtfully appointed with comfortable furnishings and soft linens to ensure a restful night's sleep. brbrOutside, the private patio area invites you to relax and soak in the stunning ocean views. Whether you're sipping your morning coffee or enjoying an evening cocktail, this serene outdoor space is perfect for unwinding and taking in the beauty of Islamorada's waters. brbrBook your stay at Maison 402 Island Charm today and experience the perfect vacation. With its prime location, luxurious amenities, and stunning ocean views, this townhome is the perfect choice for your next vacation.

Discover Maison 402 Island Charm in Islamorada: a spacious 3BR condo for 6 with stunning views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$239.16

Discounted 3 to 6 months rentals. Plan your perfect getaways to paradise. 1/1 Fully Renovated Beautifully Designed Condo. Mm76 Sleeps 4. Boat dock equipped with water, electric & cleaning station as well as boat & trailer storage first come/ serve. 300k liability insurance required for boat. Private boat ramp also available. Enjoy all the community amenities pool, tennis court, pickle ball, shuffle board, corn hole, & life size tic tac toe. Building shares a washer & dryer. Bring home your Fresh Catch & prepare it in our fully equipped kitchen with all new appliances and a fully stocked for all your prep & cooking needs. We also provide a Weber gas grill. Condo is located on the 3rd floor. Minutes from the Famous Robbie’s and Anne’s Beach. Enjoy an array of restaurants , breweries, bars, shopping, fishing charters, dive & snorkel shops as well as weekly farmers markets. Islamorada full moon parties are always a great idea. Paradise Found

Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat

Islamorada, Florida, United States

Bed

Bath

5

Sleeps

$351.08

Talk about an Atlantic Ocean View; you've found it! You will fall in love as soon as you enter the gates at Ocean Harbor. This 2 bedroom, 2 bath unit offers everything you need for Resort Style Living. Enjoy the amenities of the pool, hot tub, tiki hut, tennis/ pickle ball, dockage, clubhouse, and gorgeous landscaped grounds. The private spiral staircase off of the Florida room will take you down one flight directly to the sparkling pool. The included boat slip can accommodate a boat up to 30'. You will be boating, fishing, snorkeling, or a sunset cruise within minutes from the dock. This unit offers an assigned covered parking spot as well. Conveniently located in Plantation Key. Close to shopping, boutiques, breweries, marinas, dive shops, hospitals, and many well-known restaurants. A short commute from Miami and a beautiful drive to Key West. Contact us today to get your vacation started. brCondo association approval is required, along with a $100 fee.brBoat Insurance is required for the slip. There is no trailer storage. One Pet (dog ) will be considered.br

Ocean Harbor Paradise in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$330.79

Embrace island life in the heart of the Florida Keys! Relax on the private beach or rent a charter for world-famous sport fishing adventures.brbrThis pool-view first-floor studio features a queen bed and a twin sleeper sofa and sleeps up to 3 guests. The unit includes a convenient kitchen, perfect for preparing quick meals on the balcony with stunning resort and ocean views. Linens, towels, and free WiFi are provided for your comfort.brbrCaloosa Cove Resort and Marina offers amenities like a heated pool, beach area, and General Store. For adventure seekers, charter boats are available at our on-site marina.brbrGetting around is easy with Caloosa's free transportation app, and the Caloosa KeyCard offers free access to Founders Park, a 25-acre haven with sandy beaches and a saltwater swimming area.brNote: Guest passes to Founders Park do not include pool use.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

Flip-Flops & Sunshine: Islamorada Studio Escape

Islamorada, Florida, United States

Bed

Bath

Sleeps

$685.33

Get ready to experience an incredible Islamorada vacation at Maison 305, located in the heart of Islamorada, FL. This waterfront gem is your ticket to luxury, comfort, and tranquility all rolled into one unforgettable getaway.brbrThe moment you walk through the doors of Maison 305, you'll be greeted by a perfect blend of modern style and coastal charm. The spacious living area is decked out with elegant furnishings, calming colors, and breathtaking views of the turquoise waters that define the Florida Keys. Kick back on the plush sofas, soak in the natural light pouring through the windows, and let all your worries fade away.brbrMaison 305 couldn't be in a better spot, surrounded by Islamorada's top-notch attractions, from fantastic dining and shopping to outdoor adventures. Dive into the vibrant coral reefs at Alligator Reef, take a boat ride, or simply take a leisurely stroll through the heart of Islamorada and explore all the best local shops! brWhether you're after a romantic escape, a family retreat, or a fun-filled getaway with friends, Maison 305 promises the ultimate blend of luxury, coziness, and peace. Immerse yourself in the enchantment of Islamorada at this sanctuary. Secure your stay now and create memories that will stay with you forever.brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Charming 3-Bedroom Condo in Islamorada with Stunning Ocean Views and resort-style pool.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$476.54

Welcome to Mother Ocean! brbrThis stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room offers captivating views of the ocean, and opens up to a large screened-in balcony where you can enjoy watching the morning sunrise or spot manatees in the afternoon. The fully equipped kitchen comes with a few extra features such as a coffee bar, air fryer oven and bar seating. The master bedroom has a king-sized bed and its own private bathroom that boasts a walk-in shower, jetted tub, double vanity sinks and a water closet. The second and third bedrooms offer queen and full-sized beds and share a full bathroom. Other amenities include a washer and dryer, central air conditioning, cable TV, and high-speed internet throughout. brbrThe condo is located in the sought after Bay Harbour community on Lower Matecumbe Key. This resort style community offers a pool, hot tub, fitness center and tennis and pickleball courts. If you're an angler, you'll appreciate the 30’ deep water dock with water, electricity, fish cleaning stations, and a locked storage closet for your gear. You can rent a boat, kayaks, or paddleboards, and they can be delivered directly to your own dock. With direct access to the Florida Bay, you can head straight out to the Everglades National Park and fish the flats for snook, redfish, bonefish and permit. Or, take a quick ride to the oceanside for sailfish, mahi-mahi, snapper, wahoo and more! With close proximity to the famous Islamorada sandbar, you can experience the unforgettable crystal clear waters and relaxed atmosphere. During spring and summer, fish Channel 2 or Channel 5 bridge for the world famous “Silver Kings” (tarpon) for a fierce fight. Dockage must be reserved prior to arrival and is included in the rate. There is no trailer parking on-site, but you can try Seabird Marina for trailer parking options.brbrAt the top of the neighborhood is a local seafood market with fresh local lobster, fish, shrimp and more. 1.5 miles south you will find Anne’s Beach; A hidden gem featuring a winding boardwalk that meanders through the mangroves and sheltered picnic areas where you can have lunch while watching the ocean! Anne’s Beach is also a popular place with windsurfers, and if it’s a breezy day, it’s fun to watch them swoop and soar. Because of the expansive area of shallows in the area, the best activity is to wade and enjoy the year round warm turquoise waters.brbrIslamorada is located in the heart of the Florida Keys, offering a prime location for your vacation. Whether you prefer deep-sea fishing, exploring the backcountry shallows, diving or snorkeling the vibrant reefs, sailing, kayaking, parasailing, or windsurfing, there's something for everyone to enjoy. Just 5 minutes north is the world famous Robbies, which offers fishing and snorkel charters, a restaurant and bar, shops, parasailing, kayaks and paddle board rentals. You can even hand feed the enormous tarpon! Habanos is another local favorite, where you can experience oceanfront dining and classic Cuban cuisine. Downtown Islamorada is only 10 minutes north and offers endless restaurants, breweries, shopping, activities and grocery stores. Key West is a beautiful 1.5 hour drive south.brbrTake advantage of a local’s secret and park your vehicle and utilize the Islamorada Freebee; Our local rideshare service offering door-to-door transportation service to and from your favorite Islamorada destinations with environmentally friendly electric vehicles. It’s not only a fun alternative transportation option – it reduces traffic congestion, addresses drinking and driving, and reduces the Village’s carbon footprint. Two Tesla Model X vehicles can accommodate up to seven passengers and one larger vehicle that can accommodate a wheelchair and up to nine passengers. brbrThis could be just the getaway you need, for more information contact us at (305) 664-0077.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.brbrIslamorada Vacation Rental License #: 26-0098

3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$292.88

Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The building boasts amazing amenities like an olympic-sized, heated pool, gym, game room, party room, and a gorgeous bay-front marina. This location is the best the Florida Keys has to offer, such as award winning restaurants and world class fishing. Come and enjoy a true piece of paradise.

Eclectic Easeful Stay At The Keys!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$644.02

Beautiful views from this condo dock 32 available-brUnit C109 License Number: VR-194brbrBay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.brbrWe are new owners of this condo that has never been in the rental pool. (that is why few reviews)brComplete remodel with no expense spared! brbrThe location is quiet with the most beautiful blues and greens to make you feel like you have arrived in paradise, without actually leaving the country.brbrThis Immaculate and spacious three bedroom condominium has plenty of room to spread out with gourmet kitchen and exquisite ocean views!brbrThe Great room has expansive glass doors overlooking the ocean, queen sleeper sofa and large flat panel tv.brbrFully equipped gourmet kitchen has stainless appliances and Quartz counters. There is a full-size washer and dryer right in the condo. , Wi-Fi, scanner, printer, just bring your laptop.brbrWatch the sunrise in the morning and manatees in the afternoon, from your private screened terrace. Take a dip in the pool or relax in the spa. . All this plus private deep water protected 31'dock with lift (please note $300 dock fee).br$700 per week holiday rate for slip.brbrAcross the street is a walking, fishing, kite boarding, windsurfing beach. Within a mile is beautiful Anne's beach. Rent a boat, kayaks or paddle board, and it can be delivered right to your 31' boat dock with lift.brbrDockage is $300 per week. Sorry no trailer parking on site. (try Seabird marina).brbrLocated in the heart of the Florida Keys at mile marker 75 in famous Islamorada. Here you’ll find your perfect vacation retreat for your “Keys Getaway”. Largest sport fishing fleet in the world, outstanding restaurants, beautiful reefs and local watering holes await you.brbrWhether your sport is fishing the deep water or the back country shallows, diving or snorkeling the beautiful reefs, sailing, kayaking, parasailing, windsurfing, or kite boarding, we have it all.brbrBoat/Fishing: private deep water dock, water, electricity fish cleaning stations, locked storage closet for your gear near dock with freezer, light fishing equipment for those flying in.brbrWe are licensed with the State of Florida and Monroe County. As well as the Village of Islamorada: License Number: VR-194

Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK

Islamorada, Florida, United States

Bed

Bath

Sleeps

$250.11

Ocean Harbour K-44 - Islamorada's Desirable Ocean Harbour Condominium Complex. Remodeled two-bedroom two bath unit with a contemporary flair. Fabulous location with gorgeous unobstructed ocean views. Screened balcony lets you enjoy the beauty of Ocean Harbour and the serene blue Atlantic Ocean. Twelve professionally landscaped and gated acres at the ocean's edge includes heated swimming pool, spa, two lighted tennis courts, oceanfront clubhouse with terrace and exercise facility, tiki huts with outdoor kitchen, beach and marina. brbrIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Charming 2-bedroom oceanfront condo in Islamorada, ideal for a tropical getaway.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$630.09

Poolside Maison Matecumbe #302 - Islamorada oceanfront complex...Maison Matecumbe. The unit has one level living with three bedroom and two bath. Fully equipped kitchen with counter bar area and full dining room. The living room offers sliding doors that open into your own private screen porch, just steps away from the pool. This popular destination offers a large resort style swimming pool and hot tub with a gorgeous ocean view. Enjoy grilling your dinner under the tiki hut and relaxing at the beach without even leaving the residence. Maison also, offers covered parking and elevator. Conveniently located in the heart of the Islamorada Village close to shops, restaurants, cafes and boutiques.br If booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brVACATION RENTAL LICENSE: # 24-1223brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Islamorada's Poolside Maison 302, a spacious 3BR condo with resort-style pool in scenic Islamorada.

Islamorada, Florida, United States

3

Bed