Vacation Rentals By Owner In Islamorada, FL

The Island Palm Estates is a newly constructed estate that includes 2 separate, luxurious homes with all the modern conveniences and casual charm that a premiere island getaway should have. The homes lay out on a large secluded ocean front beach with dense palm fauna surrounding 2 amazing pools and a gym shared by both houses that includes, Weight Bench, Free Weights, Elliptical Machine and Treadmills. Each home has private parking, its own pool, and expansive oceanfront porches for entertaining, relaxing and grilling. Each house can be rented individually for a private getaway or together for a large group. Please note, we don't allow weddings on the property.. There is plenty of space for everyone to spread out and enjoy themselves on this almost 2 acre property. In addition to the two pools you will also enjoy 200' of private beach and viewing dock. brbrKey Features of Island Palm Estate:brSouth House:br-3 Bedroom / 2 Bathroom – The first bedroom features a King bed, TV and ensuite bathroom with shower. The second bedroom features a Full bed, TV and ensuite bathroom with shower. Upstairs loft has a TV and two trundle beds.br brSouth Cabana:br2 Bedroom / 2 Bathroom - Both bedrooms have Queen beds, TV and ensuite bathrooms with shower.brbrNorth House:br4 Bedroom / 3 Bathroom – The first bedroom features a King bed, water view, TV, 500 gallon fish tank and ensuite bathroom with shower. The second and third bedrooms feature a Queen bed, TV and ensuite bathroom with shower. Upstairs loft has a TV and two trundle beds.brbrNorth Cabana:br1 Bedroom / 1 Bathroom - Queen bed, TV and ensuite bathroom with shower.brbrApartment:br-2 Bedroom / 2 Bathroom – The first bedroom features a King bed, TV and ensuite bathroom with shower. The second bedroom features a queen bed and TV. Second bathroom has a shower/tub combo. brbr-Washer & Dryer in each house and apartmentbrbr-Gym with TV and half bathroombrbr-Two Poolsbrbr-Lots of outdoor space with seatingbrbr-Private 200' Beachbrbr-Viewing Dockbrbr-Enough parking for several vehicles.brbr-No Pets.brbr** 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. Offering food, sanctuary, and breeding grounds for crab, shrimp, whales, sea turtles, migratory birds, and over 120 species of fish. SPRING AND SUMMER MONTHS are greatly affected, as this is not cleared out during this time period. **

Villa

10 Bedroom Private Ocean Front Estate

Islamorada, Florida, United States

10

Bed

10

Bath

22

Sleeps

$207.19

Discover Tranquil Luxury at Our Waterfront SuitesbrbrIndulge in the epitome of waterfront living with our two exquisite 1-bedroom, 1.5-bath penthouse suites nestled within the heart of Islamorada, atop the prestigious Papa Joe’s Waterfront establishment.brbrEscape to a world of luxury and serenity at our waterfront fish camp suites. Contact us today to reserve your slice of paradise and embark on a journey of unforgettable moments and cherished memories.brbrBest Sunset Views and Waterfront Views!brbrLocated on top of the world-famous Papa Joe's Waterfront, these condos are sure to make your stay memorable while in the Florida Keys. Conveniently located right in the heart of the keys we are just a short drive to Miami / Key West.brbrPublished rates apply to extended night stays with a minimum stay of 28 nights. If you want a short-term rental, we are happy to accommodate your request on a case-by-case basis, but please note that rates will be different.

Papa Joe's Waterfront - Oceansuite 302

Islamorada, Florida, United States

Bed

Bath

Sleeps

$899.83

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

$784.25

Escape to this laid-back, oceanfront townhouse in Angler's Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life. brbrThe space has a cool, beachy feel, with soft blues, natural textures, and a cozy open layout that's perfect for hanging out after a day on the water. The kitchen's got everything you need to whip up your favorite meals, and the private patio is the best place to soak in those ocean views. For the boaters, your private boat slip is just steps away—perfect for heading out for a day of fishing, snorkeling, or exploring the beautiful waters of Islamorada.brbr The master suite upstairs features a king size bed, flat screen TV, walk in closet, private bathroom and a private balcony. The two additional bedrooms both feature a queen bed, and share a spacious bathroom. An additional sofa bed is located downstairs. brbrWhether you're here with family or friends, this laid-back spot in Angler's Reef has all the comforts you need for a relaxing, sun-soaked escape.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.

Experience luxury at Angler's Reef 150 in scenic Islamorada—perfect for families!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$204.64

Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest neighborhoods of just 40 residences.brbrThis home is bright and tropically decorated. The master suite features a private bath with shower. The second bedroom shares the hall bath with the main living area. brbrThe backyard has a large Tiki Hut to sit and enjoy the beautiful weather and an outdoor fenced in shower to rinse off after a day on the water or a bike ride. brbrThere is a large closed in air-conditioned porch right off the kitchen where you can enjoy your morning coffee as you start your day or sit and unwind at the end of each day. From the porch, you can see the private park exclusively for the neighborhood.brbrClose to restaurants, charter boats and outdoor activities. brbrThis home is the perfect spot for a Florida Keys retreat.

Off the beaten path in one of Islamorada’s hidden gem of a community!.

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$317.6

Your cozy getaway awaits in quiet Venetian Shores at this bright and airy house. Deep water canal! Easy and QUICK access to the Ocean only 2 canals away! With 3 bedrooms including 2 queen beds and 2 twin beds, this marvelous property offers a tranquil escape. Enjoy 2 bathrooms, 1 with tub and 1 with a shower. Plus an queen size futon in the living room. Bright, beautiful view and a 100 foot, deep water dock on canal, great fishing!! Separate living area. Full kitchen with appliances. Gas grill outside. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out. Pet friendly. Free access to Founders Park with pool, beach and pickle ball courts only 1 mile from home. https://fl-islamorada.civicplus.com/435/How-to-Obtain-a-Founders-Park-Guest-Pass

Comfortable, Spacious 3-BR, 2-BA-1 level home- DEEP dock on canal, Islamorada

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$379.2

Located 90 minutes from Miami and 20 minutes to the world-famous Tiki Bar sandbar (dock to anchor) one of the best in the Keys. Enjoy easy and quick access to the bay or ocean via Snake Creek, excellent fishing/water activities, dining, and amazing sunsets. There is a marina located nearby that sells fuel, bait, ice and offers boat rentals.brbrThis is a 2 story property, 4 bedrooms and 2 bathrooms are on the 2nd floor, the first floor has a kitchen, living room and full bathroom. The deep water canal is double-wide and you have 70' of dock.brbrThere is 28 night minimum stay required and offered for rent October 1 - April 30.

Escape to beautiful Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$206.57

Wake up and enjoy sunrise on the pier over the Atlantic and walk across the street at night and watch sunset on the Gulf. You can take a dip in the pool or play a game of pool in the club house. Visit one of the many local restaurants (some close enough to walk to) or prepare dinner yourself in the beautiful kitchen or grill a steak outside by the ocean. Fish off the pier or book a fishing trip!

Condo on Islamorada on the beautiful Atlantic Ocean.nCome enjoy and relax!

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$708.96

This stunning pool home is nestled along a private canal with convenient dockage and quick access to the bay! This luxurious getaway is the definition of relaxation and waterfront living, offering an unforgettable vacation experience.brAs you step into this home, you'll be greeted by a spacious and tastefully decorated living area, designed to create a comfortable and inviting atmosphere. The large windows provide breathtaking views of the peaceful mangrove hammocks across the canal, and allows natural light to illuminate the space and creating a serene ambiance throughout the day. You will find 3 bedrooms and 2 bathrooms upstairs all perfectly furnished to meet everyone in your parties desires. br Bring along your friends & family as this home has a private downstairs apartment 1 bedroom, 1 bathroom with a kitchenette. brThe highlight of this home is undoubtedly the private pool, inviting you to take a refreshing dip or soak up the Florida sun on the comfortable lounge chairs by the poolside. brAdditionally, this vacation rental offers convenient amenities such as a barbecue grill, wifi, and a washer and dryer. Furthermore, the home is ideally located near popular attractions, restaurants, and shopping destinations, ensuring that you have easy access to everything you need for a memorable vacation.brExperience the perfect blend of luxury, comfort, and waterfront living as you create lifelong memories in this incredible retreat.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.

Canalfront 4-Bedroom Mangrove Sunset in Islamorada with dockage and 2 boat lifts

Islamorada, Florida, United States

4

Bed

Bath

8

Sleeps

$412.27

Escape to Sun Outdoors Islamorada in the Sport Fishing Capital of the World. Live your best Keys life in this beautifully designed 2 bed, 2 bath oceanfront home in a prime resort location. Start your mornings with coffee on your private balcony as the sun rises over the Atlantic, then spend your days boating, fishing, snorkeling, or diving some of the best waters around. When it’s time to kick back, you’re just minutes from iconic tiki bars, local restaurants, shops, and grocery stores—everything you need for effortless island living. Bring your boat—there’s a marina on site with a slip for up to a 20’ boat, plus resort-style amenities including a pool, beach area, food truck, and a clubhouse with games, ping pong, gym, and fun community events. Sunshine, salt air, ocean views, and laid-back luxury… you just found your new favorite vacation location. brbrPlease inquire about dockage availability and pricing. brbrSun Outdoors Islamorada - Waters Way brMM87 Oceanside brbr28 night minimum. Please inquire for rates and availability.

Sun Outdoors Islamorada ~ Beautiful Oceanfront 2 Bedroom Home

Islamorada, Florida, United States

Bed

Bath

Sleeps

$518.88

Palm La Mar, a luxury vacation rental located in the exclusive oceanfront gated community of Anglers Reef in Islamorada, Florida, The Sportfishing Capital of the World.brbrThe two story Key West style house has 2 master bedrooms on the second floor, furnished with king beds, ensuite bathrooms, and private balconies. The first floor has a half bathroom, full kitchen, dining room, and living room with sleeper sofa. brbrThe gated community of Anglers Reef offers a resort feel with detached villas, quaint streets, a 75 foot heated pool overlooking the Atlantic Ocean, and two private beaches. The property is neighborly, safe, and immaculately landscaped for pleasant walks day and night. Anglers Reef is in close proximity to restaurants, Starbucks, entertainment, bars, and water activities, many within walking distance. brbrThere is a private marina on a deep channel directly out to the Atlantic Ocean. Not all homes at Anglers Reef have a boat slip, ours does! The slip is available to rent for $350 per week (please notify us if you will be wanting the boat slip). The slip accommodates up to a 31 foot boat and has fresh water and electrical connections. There is a nearby public boat ramp at Founders Park to launch your boat. Two fish cleaning stations are available at either end of the marina. Manatees, fish, and lobster can be seen right from the dock. You can even drop a line and catch a fish! brbrYou are less than 5 minutes from the locals' sandbar and 10 minutes from the world famous Islamorada Sand Bar. Take your boat out for ocean or bayside fishing, snorkel the crystal clear waters of Alligator Reef, grab a meal at a waterfront restaurant, and end the day with a sunset cruise! br brIncluded in your stay are kayaks, beach towels, beach chairs, a cooler, Weber gas grill, Big Green Egg grill, and patio table with chairs. Inside the house, there are stainless steel appliances, cookware, silverware, linens/towels, washer/dryer, wifi, 3 smart flat screen TVs, Xfinity cable TV, and Alexas.brbrThere are 2 designated parking spaces, one of which is covered by a carport. brbrThe property is licensed for a maximum occupancy of 4 adults plus 2 children. No Pets. No smoking. brbrAny questions, just ask! We look forward to having you.brbrFollow us on Instagram at palmlamarbrbrPALM LA MARbr107 Anglers Way, Anglers ReefbrVacation Rental License #26-0096

Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community

Islamorada, Florida, United States

Bed

Bath

Sleeps

$372.19

Enjoy this quiet, peaceful retreat in the desirable Venetian Shores neighborhood of Islamorada. Located on a quiet plugged canal, this spacious home offers a relaxing setting perfect for unwinding and enjoying the Florida Keys lifestyle.brbrThe home features 4 bedrooms and 3 bathrooms, providing plenty of space for families or groups to spread out comfortably. Outside, you'll find a heated pool and generous outdoor space ideal for relaxing in the sun, dining outside, or enjoying the warm island breeze.brbrWith its peaceful location and roomy layout, this Venetian Shores home is the perfect place to relax and enjoy your time in the Keys.brIf booking more than a year in advance current prices may not reflect the 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. brPlease 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.

Discover comfort at 139 Venetian Way, a spacious 4BR getaway in Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$227.95

Enjoy breathtaking sunsets from your very own private beach in this Florida Keys Chic townhome!!! Beautiful 3 bedroom 2 bath located in Islamorada, Florida Keys. Directly next door to Founders Park.

Florida Keys Chic

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$292.87

Welcome to Coral Harbour Club! brbrFind your escape, experience relaxing days at this oceanside getaway! Located on Plantation Key in Islamorada, this 2 bedroom, 2 bath condo is equipped to sleep six adults, with the bedding arrangements of one king bed and two queen beds. The oceanfront marina and swimming pool, private clubhouse, saltwater lagoon, and tennis courts are ready to make your stay at Coral Harbour a memorable one.brbrEnjoy your month-long vacation in your own little tropical oasis. Savor your morning coffee out on the terrace or bring down the screen and take advantage of the cool ocean breeze. Don’t feel like cooking You’re in luck, this condo is only a short drive away from some of Islamorada’s best dining – casual and upscale.brbrFinding dockage is not a problem as this unit comes with a boat slip. The protected onsite, oceanside marina can accommodate up to a 30’ boat. This marina also has its own boat ramp, fueling station and ice machine. Only minutes away from the famous “Alligator Lighthouse,” snorkeling, diving and all kinds of fishing! Additionally, there is easy bay access with Tavernier Creek and Snake Creek nearby. There is no trailer parking onsite, but you can try the Plantation Yacht Harbor at Founders Park for trailer parking options.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.brbrPlease book 45 days advance so HOA can approve guests and reservation.

Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$510.29

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

6

Sleeps

$215.09

Escape to Islamorada and enjoy the laid-back lifestyle of the Florida Keys in this 2-bedroom, 2-bathroom condo at Plantation by the Sea. This charming getaway offers a comfortable stay in a gated community with fantastic amenities—perfect for your next vacation!brbrStep inside to find an inviting living space with coastal-inspired décor, a fully equipped kitchen, and all the comforts of home. The primary bedroom features a king-size bed and a private ensuite bath, while the second bedroom provides a cozy retreat for family or guests, with easy access to the second full bathroom.brbrYou're just a short walk to the heated pool, fitness room, and sauna. Take a relaxing dip, unwind after a workout, or stroll down to the private fishing pier, where you can soak in the ocean breeze and watch stunning sunrises over the Atlantic.brbrLocated in Islamorada, you're minutes from world-class fishing, delicious waterfront dining, and unique local shops. Whether you're planning a quick escape or an extended stay, this condo offers the perfect mix of comfort and convenience.brbrBook your stay today and experience the best of the Florida Keys! 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.

Cozy 2-Bedroom Condo in Islamorada Plantation By The Sea

Islamorada, Florida, United States

Bed

Bath

Sleeps

$191.95

This two-story house is located on an ocean access canal that is literally minutes from the Atlantic Ocean. Guest can dock their boat (max. length of 32') in the backyard and be on the Ocean in just a few minutes. The front of the house faces the Atlantic Ocean with views of the ocean. The home is updated and has an open layout with volume ceilings. The master bedroom has a queen size bed with attached master bathroom. The second bedroom has bunk beds with a trundle, which sleeps 5 people. The great room has a love seat, and a sleeper sofa, which sleeps 2 adults. Guests can enjoy views of the ocean from the balcony. There is covered parking for 2 cars.

Beautiful water front home, private dock in Islamorada, World Fishing Capital

Islamorada, Florida, United States

Bed

Bath

9

Sleeps

$227.14

This Islamorada apartment boasts 2 inviting bedrooms with 2 queen beds. The cozy living room also offers an extra queen bed for additional guests. Enjoy the enchanting atmosphere of this fabulous rental, complete with WiFi, heating, AC, and more. With 2 bathrooms equipped with hair dryers and showers, guests will feel right at home. Our place will help you feel at home while you're traveling in Islamorada.

Apartment

Amazing new 2-bedroom, 2-bathroom apartment in the heart of Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$247.5

Are you ready for modern day pirate life Wonder how the locals live Well then we can show you ! Redneck paradise, Primitive stay experience 4:20 & pet friendly. “ glamping on water”. Private cabin on our boat hosted directed & maintained by us onboard during your stay. fishing from anchorage, snorkeling, lobstering & swimming, cook & catch meals, nightly dinner, morning coffee & pastries included. A true local experience! Includes parking & shuttle to & from boat. Additional amenities available for additional fee such as reef trips , dingy rental, kayaking. Deck swabbing at no additional charge!

House Boat

“ The Ultimate redneck” boat experience

Islamorada, Florida, United States

1

Bed