Home Vacation Rentals By Owner In Islamorada, FL

Showing 380 Of 715 Vacation Rentals
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$373.26

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Condo

Relax at Ocean Harbour K-35, a 3-bedroom oceanfront condo with dockage

Islamorada, Florida, United States

Ocean Harbour K-35 - This newly renovated unit is located in Ocean Harbor, one of the most exclusive condominiums in Islamorada! Enjoy this beautifully furnished three-bedroom, two-bathroom unit with endless views overlooking ocean. This 12-acre property is truly an island paradise, complete with tropical landscaping, heated pool, beach, marina, tennis courts, clubhouse, fitness room and much more. The rental includes a 30' slip in the on-site protected marina, complete with water and shore power, fish-cleaning stations, boat ramp and barbecue grills to cook your fresh catch. 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. 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.
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Exceptional(1)

$127.59

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Apartment

Beautiful Studio Apartment - Summer Sea Condo #230

Islamorada, Florida, United States

Summer Sea Condominium Unit 230 is a brilliant, clean and modern efficiency apartment, upgraded with tile throughout and furnished with a murphy bed for more space. Minimum rental of 2 months when renting February. While the balcony faces roadside, the condominium is right on the bay with two pools (one heated), a marina and beach area, workout room, game room, community room, Laundry rooms and free community Wi-Fi , fabulous sunsets and friendly residential atmosphere. Safe and secure gated community. Second floor apartment with elevator access. No Pets and no smoking at the request of the owner. Rentals are by the calendar month, limited to a minimum of 28 days*. brbrFeatures/Location DescriptionbrSummer Sea is a multi-story residential waterfront condominium with a friendly atmosphere with on-site management. The perfect place to spend your vacation. This condominium is on Plantation Key just north of the famous Marker 88 Restaurant, a 5-star gourmet restaurant with outside bar. Four restaurants within walking distance. The complex is located at mile marker 88.5 which is within The Village of Islamorada. With an abundance of community areas such as a beautiful sandy area and lots of space to stretch, large, shared kitchen/entertaining area, game rooms, a gym, beach, 2 pools (one heated), laundry rooms etc. br28-day minimum, Minimum rental of 2 months when renting February. No Pets, No Smoking.brFlorida Lease required. application and background check performed by the condominium is required. Summer Sea Condominium requires a 5-day notice, and their $200 fee is nonrefundable. If you cancel your reservation, a 3% cancellation fee will be charged to cover costs. Please note that the security deposit will be held against your credit card three days before your arrival and released after departure. This is not a charge, just a hold until it can be verified that there is no damage. Feel free to inquire for all details.brOffered through Blue 9 Realty Inc., DBA Keys Vacation Brokers, Jonelle Kop, Tavernier, FL
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Exceptional(60)

$403.39

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Private Vacation Home

Villa located on the waternFree marina, and trailer parking.

Islamorada, Florida, United States

brPrivate, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare), the villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with night lights, power and water.brbrFree onsite boat ramp, marina, and trailer parking.brbrThe villa itself comes with a fully-equipped kitchen, washer and dryer, linens, queen and king beds, Cable TV, VCR, and a Florida room for dining. Windows in the living room and bedroom cover two thirds of the wall giving the feeling of the outdoors being in during the day and easy open/close window coverings provide privacy at night. This is a small house, near the water, no high-rise, no canal, and no density of people problem. This is a laid-back atmosphere for those who desire it.brbrLocated on Upper Matecumbe Key, the downtown area of Islamorada, the property is quiet and hidden. Boats up to 25' are secure in our protected marina. Most trailers are able to launch from the property but a few extra-wide may have to use nearby launching places. There is trailer parking on the property as well as two parking places per unit. There are seven units on the property.brbrbrFree use of the village park(tennis, pickle ball, beach, pool, and dog park) is provided to guests. There are three state parks in the Islamorada area and the owner will provide passes. You are within walking distance to the best restaurants, shopping, and attractions. Free electric taxis are able to take you anywhere in town. Grocery, fishing and boating supplies are conveniently close.br brIslamorada proudly calls itself the 'Fishing Capital of the World' and fishermen love us!brLocated close to the best backcountry fishing on the edge of the Everglades, we are also able to easily access reef and blue water fishing. Our immediate bay provides fun catching tarpon and easy fishing on our seawall at night is a guest favorite. Owner has names of boat rental places and guides for all types of fishing and snorkeling. Next door to us is Back Country Cowboy. They rent kayaks, canoes, paddle boards, as well as bicycles. our bay is the perfect, protected area for all water activities. Oceanside, we have some of the best snorkeling and scuba areas in the Keys!brbrThere's never a dull moment at our marina. We have an Osprey nest nearby. If you clean fish, you'll have lots of bird friends. Other visitors are manatees, octopi, and nurse sharks.brThis property is treasured by guests and owners alike. The privacy is wonderful, the property peaceful, and the villas kept clean and updated. Most of our guests come year after year. Some have met friends one year and make the same dates together the next year. The size of the property is perfect- not too big, just right.brbrThree or four years ago, Fox News had a US Best Sunsets contest. Someone submitted one of our guest's pictures and we recognized it! Our sunset won over thousands submitted. Come and enjoy the best The Keys has to offer. Best location, best property, best fishing, and the best sunsets.
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Exceptional(12)

$760.36

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Private Vacation Home

Sandy Beach Cove ️ ️ Gated Private Beach Home Plus Cottage Oasis , With Dock

Islamorada, Florida, United States

**(Now For Limited Time!. Listed nightly rate includes a 40% Discount On All Stays of 28 days min.!!)**. Relax ,Enjoy and Indulge yourself with Family and friends on this Over Half Acre Private Ocean Beach Oasis ️ ️ with dock , your own Private boat ramp and available boat space up to 28’ feet . Over 2624/sqf of beautiful and professionally decorated living spaces. Located on the center of one of the most pristine and desirable strip and walking/jogging/bicycle trails of Islamorada ( strip and trail extends 2 1/2 mile North of the property to Florida Keys famous Robbie’s restaurant and Market place , here you will find great brunches , cocktail’s and ocean views . you will also find , boat, Jetski’s rentals , fishing . snorkeling and Beautiful sunset charters and even parasailing . Trail also extends 2 1/2 miles South of the property, to Anne’s Beach and Islamorada Chanel 2 Bridge. Come and Experience The Ultimate Resort -Like Style Living and Adventure, on this Elusive , Unique , Exclusive and Luxurious Piece of Paradise ️. The Beach Water of this Islamorada Oasis are Crystal Clear and Notoriously Shallow , Making it , just Perfect For Spending the Day on The Water and Enjoying Activity Favorites such as , Kayaking, Snorkeling, or just Refreshing And of Course Relaxing . The Main House and Cottage has total of 4 bedrooms and 4 full bathrooms . The Main House has 3 large Bedrooms 1 with King size and 2 with Queen size beds . 3 full Bathrooms. Full size Kitchen with appliances ( dishwasher, coffee maker, microwave, blender, toaster all cups , plates and utensils included), large central Kitchen Island that seats 5, Dining Room Table ,Living Room and Magnificent Atlantic Ocean and Wild Life Views from just about all locations inside the house and even more astonishing views from the Large Tropical (Heated/Chill) Swimming Pool, Patio , Private Beach and Dock . The Cottage house is beautifully decorated and has 1 Bedroom with (King size Bed), 1 full Bathroom , Full Kitchen with appliances, center Island that seats 4 and Living Room w sofa. ( also avail. deluxe foldable twin mattress) . This Compound comes with Kayaks , Bicycles , Fire Pit / Grill , BBQ Grill , towels, linen plus much more (“Hobie tandem Island adventure” sail boat⛵️also available during your stay. upon request**). World Famous Alligator Reef and Light House only minutes away by boat and visible from property. This is a New property to the market!!! …5 stars ⭐️ host to another gorgeous Islamorada property offering 6 bedroom with 4 full bathrooms and 130’ feet of dock space, Tropical Paradise”. Located just 1.5 miles .vrbo ID 1909688. **Please contact Host for shorter 1 or 2 weeks “early check out options “ and for days not available on calendar.**
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Exceptional(1)

$683.17

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Private Vacation Home

Ultimate Islamorada Oasis with Pool, Dock, & More

Islamorada, Florida, United States

Welcome to your own island oasis! This beautiful 4-bedroom, 3-bathroom canal-front home blends luxurious coastal modern design with meticulous attention to detail. From the moment you step inside, you’ll be captivated by the high-end furnishings and chic island decor that create a warm, inviting atmosphere throughout. The state of the art kitchen, spacious living area, and cozy bedrooms featuring plush kid size beds, make this perfect spot to relax and unwind. One bedroom includes a fun double bunk perfect for kids or guests, adding a playful touch to the home’s comfort. brbrThe heart of the home is its outdoor living space, with a custom-built summer kitchen, sparkling pool, and turf yard, providing the perfect backdrop for relaxation and entertaining. Enjoy the best of both worlds with plenty of deepwater dockage and a private backyard area surrounded with tropical landscaping and mangroves. Villa Azul offers the perfect island backyard oasis, once you check-in you'll never want to leave. brbrLocated in desirable Lower Matecumbe, this home offers immediate access to the Atlantic Ocean and some of the best fishing spots in the world. While close to local attractions, including world famous tiki bars, local restaurants, and great shopping, this retreat retains a laidback vibe, offering a tranquil escape from the hustle and bustle.brbrWhether you're here to relax, explore, or indulge in boating activities, this stunning coastal haven provides the ideal setting for your vacation.brbr28 night minimum. Please inquire for rates and availability.brbrVilla Azul ~ MM76 Oceanside
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Exceptional(19)

$981.58

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Private Vacation Home

Marlin House @ Tarpon Point

Islamorada, Florida, United States

Summary:brStunning ocean views from all living levels & a waterfront pool!brbrThe Space:brWelcome to the captivating Marlin House, an extraordinary 4-bedroom, 4-bath retreat nestled in the scenic paradise of Islamorada. Prepare to be enthralled by its exquisite design, unparalleled amenities, and sweeping ocean vistas that grace every level of this remarkable abode. Your journey begins as you pass through the gates of Tarpon Point, an exclusive enclave comprised of just twelve oceanfront residences. Within this private sanctuary lies Marlin House, waiting to envelop you in a world of sheer luxury.brbrAs you step foot inside Marlin House and ascend to the main living level, a symphony of awe-inspiring ocean views unfolds before your eyes. The sheer beauty of the surrounding turquoise waters will leave you breathless. Adjacent to the living area, an elegant dining room and a chef's kitchen beckon, promising unforgettable culinary experiences and convivial gatherings. This level also houses the first of three splendid guest bedrooms, each adorned with expansive closets to ensure ample storage space. In addition, every bedroom and the living room boast internet-enabled smart televisions, offering seamless access to your preferred streaming services.brbrVenture up to the third living level, where two more resplendent guest bedrooms await, each boasting its own ensuite bath. As you stroll down the hall from the guest bedrooms, prepare to be captivated by the main bedroom, a sanctuary that epitomizes refined coastal living. With its breathtaking ocean panoramas, a sprawling private balcony, a cozy reading nook, and a generously sized closet, this tranquil haven invites you to unwind in blissful serenity. The ensuite bathroom is an oasis of indulgence, featuring a sumptuous soaking tub and lavish Toto fixtures, ensuring a pampering experience beyond compare.brbrBeyond the confines of Marlin House, the gated property offers a wealth of amenities designed to enhance your stay. Immerse yourself in the refreshing embrace of the community waterfront pool, bask in the sun-drenched beach area, or cast a line from the fishing pier, all while enveloped in the meticulously landscaped grounds that surround this coastal retreat.brbrMarlin House beckons, promising an escape to a world where luxury meets coastal splendor. Experience the epitome of refined living, where every detail has been carefully curated to exceed your expectations. Unleash your senses to the breathtaking ocean views, savor the state-of-the-art amenities, and allow yourself to be swept away by the sheer beauty that awaits within these hallowed walls. Your perfect getaway starts here, at Marlin House, where memories are made and dreams come true.brbrThis home is managed by The Florida Keys Rental Store. For recommendations or things to do while in the keys, we have all the information you could need. Over 20 years in the business, we know what it takes to make your trip the best one yet!brbrNotice to Guests:brTarpon Point is not a rental community or resort.  The homes are private homes and are the private property of the owners, some of whom live there full time.  You need to be aware that you are sharing common areas with owners of the Tarpon Point Community.  As a guest, it is imperative you ensure  all of your party are respectful of both the private property in and around each home and respectful in your use of the common areas
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$453.73

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Private Vacation Home

Stunning 3-bedroom home in Islamorada with private heated pool and ocean views.

Islamorada, Florida, United States

Indulge in a retreat to paradise at this exquisite 3-bedroom, 3-bathroom oceanfront home on the captivating shores of Islamorada! This haven not only presents breathtaking ocean views but also features a private pool and a delightful tiki hut, providing an ideal blend of relaxation and outdoor enjoyment. Whether it's sipping morning coffee on the balcony or enjoying sunset cocktails beneath the tiki hut, this house caters to every preference.brbrThe living space sets the tone with a laid-back atmosphere, embodying the essence of island living. Expansive windows frame sweeping ocean panoramas, establishing a tranquil backdrop for your escape. The open-concept design seamlessly links the living and dining areas, creating a cozy space to unwind after a day of sun-soaked adventures.brbrAccommodating up to six guests, the three bedrooms and bathrooms ensure a comfortable stay. Whether you're a family seeking an adventure-packed vacation or a group of friends desiring a laid-back getaway, this oceanfront retreat guarantees a restful night's sleep for all.brbrStep into your private outdoor oasis, where a glistening pool beckons. Take a refreshing dip or soak up the Florida sun on the poolside deck. Adjacent to the pool, the charming tiki hut offers a shaded retreat perfect for enjoying a refreshing drink or simply soaking in the stunning ocean views.brbrBeyond your secluded haven, Islamorada invites water enthusiasts and nature lovers to a myriad of activities. From fishing charters to exploring nearby reefs, the opportunities abound for creating enduring memories in the heart of the Florida Keys.brbrDon't miss the chance to embrace the ultimate oceanfront getaway. Secure your reservation now and submerge yourself in the laid-back allure of Islamorada's coastal paradise!brbrDon't miss the chance to embrace the ultimate oceanfront getaway. Secure your reservation now and submerge yourself in the laid-back allure of Islamorada's coastal paradise!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.
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$1176.81

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Condo

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

Islamorada, Florida, United States

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.
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Exceptional(119)

$739.06

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Private Vacation Home

4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL

Islamorada, Florida, United States

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! brbrThe porch off the family room offers ocean views, 2 comfortable chairs w/side table, an outdoor dining table seating 4-people and a grill. brbrThe second floor includes 3 bedrooms. Upstairs, the master bedroom features a four-poster king bed, en-suite bathroom with double sinks and an updated shower with bench. The master bedroom opens up to its own private covered porch with spectacular views of the ocean, 2 sofa lounge and 3 club chairs. The two upstairs bedrooms offer queen beds with a partial ocean view. There’s a full bathroom located between these two rooms. You’ll conveniently find a laundry closet with washer and dryer in the upstairs hallway that also offers a steamer and iron. All bedrooms include TV’s and wireless internet service provided. brbrThis rental includes boat slip #14, which can accommodate boats up to 31 feet in length. Angler’s Reef is a wonderfully maintained and gated community in Islamorada, the fishing capital of the world. In Islamorada you can swim with dolphins, go dive the reefs, sport fish or just simply enjoy the salt-water life and great restaurants.
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