Vacation Rentals By Owner In Islamorada, FL

Showing 100 Of 715 Vacation Rentals

$254.99

2-bedroom home with stunning ocean views in a resort!

Islamorada, Florida, United States

Prime location for a relaxing stay, take in the views of the Atlantic from your private balcony. This 2 bedroom,2 bath, has everything that you would need to make this your best vacation ever! brbrWhile here, you will have access to all the resort clubhouse amenities or, play some billiards, work out in the fitness room or just hang out along the boardwalk to read a book or watch the sun setting from a rocking chair. Walk across the street to Founders Park and enjoy beach access or a game of pickle ball. It’s all up to you. brbrThe home is privately owned and decorated, brA min of 28 nights is required for these homes.

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$254.99

/ Nightly

Private Vacation Home

Amazing 2-bedroom waterfront resort home! Minimum 28-Day Reservation Required

Islamorada, Florida, United States

Sun Outdoors resort offers first class amenities, in the heart of Islamorada, near many restaurants, and across the street from Founders Park. brbrMake yourself right at home behind controlled access gates. Enjoy amazing views of the Atlantic, and be a social butterfly when you want to join others at the Resort Clubhouse. The resort offers a social calendar and events, or privately entertain in your own home. Lay back and enjoy the Isla Life your way! brbrThe home is two levels, with parking underneath. Primary bedroom upstairs, secondary bedroom downstairs. Both floors have full bathrooms. Home is furnished with everything you would need, brbrDisclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.brbrMinimum 28-day reservations required.brBedding Configuration: King bed, 2 Twin beds, Futon

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Exceptional(4)

$277.57

/ Nightly

Private Vacation Home

Enjoy the Ocean from the deck of this 2BR. Minimum 28-Day Reservation Required

Islamorada, Florida, United States

This beautiful home has stunning views of the Atlantic Ocean. This home has 2 full two bedroom, two baths and is fully furnished - just bring your suitcase. brbrWhile here, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including, a heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee.

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$274.07

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Apartment

Charming 2-bedroom apartment with WiFi, AC in serene Islamorada. 75' dock

Islamorada, Florida, United States

Islamorada is waiting for you at this superb 2-bedroom apartment. With a king bed, a queen bed, and a cozy living room with a sofa bed, this place is perfect for a small group of guests.brOutdoor protected bar. BBQ, bait freezer. 75' dock, Boat ramp in the community & Private beach Plenty of parking & Fenced yard. br Feel free to reach out to us during your stay - We're happy to suggest local spots to check out.

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Exceptional(4)

$1588.39

/ Nightly

Cottage

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Islamorada, Florida, United States

The recently renovated Oceanside Cottage is located directly on the ocean with amazing morning sunrises over the ocean. The full moon rise over the water in front of the house is breathtaking! brbr2 Bedroom - 2 bath Modern Cottage: brThe cottage has a beautiful cook's kitchen equipped with brand new appliances. Each bathroom is entirely new with modern fixtures including glass showers. There are 2 bedrooms, each with a private full bathroom. The brand new king sized mattress sets are known as the famous Westin Heavenly. Each bedroom has a beautiful view of the water through a private sliding glass door that leads to a oceanfront deck. The pool sits squarely in front of the cottage and has a stunning white marble pool ledge patio overlooking the ocean.brbrA constant onshore breeze drifts through the house with pure, invigorating ocean scents. The house sits across from the Alligator Lighthouse, an amazing snorkeling spot, and snorkeling at Cheeca Rocks is just a few moments anyway by boat. The dock easily accommodates one bay style boat with immediate access to deep water. brIslamorada has fantastic restaurants, cafés, bakeries, marinas, charters, and needless to say it is the fishing capital of the world. There is so much to enjoy!brbr2 Paddle boards and 2 kayaks are included with rental as the waters off the house are perfect for exploring by kayak. There is a teak cabana for rest and relaxation by the pool. brbrThe house is a 100% non-smoking property.brbrAbout the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel and is exceptionally clean and easy to enjoy.brbrWe privately own a total of 5 boutique vacation rentals in Islamorada:brVRBO listing #1576833 (5 bedroom)brVRBO listing #1054019 (5 bedroom)brVRBO listing #1977457 (7 bedroom)brVRBO listing #3363008 (6 bedroom)brVRBO listing #689629 (5 bedroom)brbrLICENSE #: 26-0147 - Islamorada

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Exceptional(1)

$278.64

/ Nightly

Private Vacation Home

Oceanview 2 bedroom with jaw-dropping views! Min 28-Day Reservation Required

Islamorada, Florida, United States

This home is in a resort. This is a 2bedroom 2bath home, Home has stunning views of the Atlantic Ocean. Home sleeps 6 and is designed to make all guests feel at home, offering upgraded features as in stainless steel appliances, a farm sink, quartz countertops, and plenty of storage. The floorplan has open kitchen living area a private deck with awesome views.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

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Exceptional(2)

$278.64

/ Nightly

Private Vacation Home

Oceanview 2BR home in a pet-friendly resort! Minimum 28-Day Reservation Required

Islamorada, Florida, United States

Home is located in an ocean front resort. This 2 bedroom 2 bath home is pet friendly. Home has amazing views of the Atlantic Ocean. Home sleeps 4 persons and is designed to make its guests feel at home, offering upgraded features as in stainless steel appliances, a farm sink, quartz countertops, and plenty of storage. The floorplan has an open kitchen living floorplan and a private deck with awesome views.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

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$195.92

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Private Vacation Home

Serene 2-bedroom townhome with AC in charming Islamorada

Islamorada, Florida, United States

Make yourself at home in this 2-bedroom Islamorada townhome retreat. The space features a king bed and a 2 full beds, comfortably accommodating guests. With two bathrooms that include refreshing showers, getting ready is a breeze. Stay comfortable year-round with heating and air conditioning.. This lovely, peaceful townhome offers the perfect spot to unwind after a day of exploring. Kick back, relax, and enjoy everything Islamorada and our townhome has to offer.

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Exceptional(9)

$518.56

/ Nightly

Private Vacation Home

NEW Luxury Modern Coastal Home in Islamorada

Islamorada, Florida, United States

This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada and the Florida Keys this 2 story home offers access to both the Gulf and Atlantic, has its own private recreational room with pool table and right outside you will find a modern heated pool with spa! brbrThis home offers 3 bedroom and 3 full baths (2 en-suite) upstairs and 1 room and 1 full bathroom first floor in recreational room. Bedroom breakdown: 1 king room, 1 queen room, 1 twin room, 1 rec room with queen sleeper. Sleeps 8 comfortably and we offer Corduroy’s famous convertible bean bag that converts to twin. The recreational room has a sleeper sectional, large 75 inch flat screen tv and new pool table. brbrHome has a full kitchen on second floor with everything you need to make a home cooked meal. Kitchen island features 4 counter stools and dining area accommodates 6-7 guests. All rooms including family rooms have their own NEW smart TVs. Family room TV 65 inch flat screen. In October 2022 will add a bar and mini fridge in the recreational room for further convenience.brbrBring your boat up to 40 feet! You will have your own slip located just steps (less than 30 seconds away) from the home. There is parking right in front of the boat for unloading/loading if needed. It is very convenient! brbrThe home is gorgeous and you will be among the first to stay! Everything is brand new just for you! We make it convenient to just move in by offering a full Keurig Coffee Bar where you can make your own latte and cappuccino! Offer shampoo and conditioner in all bathrooms, offer laundry detergent, dishwashing soap and dishwasher detergent, toilet paper and paper towels!brbrPlease inquire if thinking of bringing a pet:)brbrWe welcome YOU to stay in paradise!

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$2493.63

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Private Vacation Home

Turtle Cove: Stunning 7-bedroom home in Islamorada with a private pool and open water views.

Islamorada, Florida, United States

Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that makes you realize your vacation has started. Each cottage has it's own personality with an array of unique, yet tasteful decor. The property offers a boat basin, tiki hut, oceanfront pool, outdoor showers, paddle boards, kayaks and bikes. All of this combined to make the perfect family retreat. Your own little oasis you'll never have to leave. brVR#24-0385, 24-0386, 24-0416, 24-0134brbrIf 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)

$369.28

/ Nightly

Private Vacation Home

Experience luxury at Salty B in Islamorada with private pool and canal views!

Islamorada, Florida, United States

Nestled within the prestigious Venetian Shores community, this captivating canal front duplex offers a remarkable blend of elegant design, luxurious living, and the allure of an inviting poolside retreat. This resplendent residence showcases meticulous interior design and an enchanting outdoor oasis, making it the epitome of Florida Keys living.brbrThis home offers 2 bedrooms and 1 bathroom upstairs and 1 bedroom and 1 bathroom downstairs all complimented with bedding that will guarantee a peaceful night of sleep. The living space exudes opulence with carefully chosen furnishings, striking the perfect balance between cozy and elegant. brbrBring your boat and enjoy the luxury of hopping on in your own backyard and being minutes away from the Atlantic Ocean and the Florida Bay. Located perfectly to great fishing spots, the Islamorada Sandbar and tons of restaurants accessible by boat! The dock is exactly 35' long. Please make sure your boat (engines included) is 34' or less.brbrThis Venetian Shores canal front duplex serves as the ultimate retreat for an unforgettable Florida Keys vacation. With its impeccable decor, private pool, and access to the mesmerizing waterways, this vacation rental promises an unparalleled experience of luxury and relaxation. Book your stay today and immerse yourself in the serenity and beauty of this enchanting coastal paradise.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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$307.38

/ Nightly

Private Vacation Home

Charming 3BR canal home in Islamorada with private yard and boat slip.

Islamorada, Florida, United States

Welcome to your perfect home away from home! In the heart of Islamorada, this Venetian Shores house is ideally located, offering easy access to the area's dining, shopping, and recreational attractions.brbrVenetian Shores is renowned for its deep-water canals, making it a paradise for boating enthusiasts. The private dock at this residence provides direct access to the open waters of the Florida Bay and the Atlantic Ocean, allowing for easy exploration of the Florida Keys' crystal-clear waters, coral reefs, and world-class fishing.brbrThis Venetian Shores gem in Islamorada, Florida, is the embodiment of Florida Keys charm and tropical living. With its stunning water views, thoughtful design, and access to the region's unparalleled natural beauty, it's the perfect place to call home in the Florida Keys.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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$4806.62

/ Nightly

Private Vacation Home

Island Beach House Oasis Your Memory Maker awaits

Islamorada, Florida, United States

***Notwithstanding anything in the rates page the minimum renal is 28 days***brbrThere is luxury, luxury and unrivaled, and then there is the Bay front Island Beach House Oasis that offers that and more. Situated on just a hair under one acres of manicured Islamorada shore front, this unique property reveals the very best in tropical vacations. The property only recently became available. Sleeping 16, the six-bedroom, five-bathroom retreat will conjure reveries of leisure taken to new heights.

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$562.5

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Apart-hotel

Penthouse Suite: 2-bedroom with AC and a stunning view in charming Islamorada

Islamorada, Florida, United States

This 2-bedroom penthouse suite is perfect for your escape to Islamorada. Guests enjoy two bathrooms (4 beds), providing plenty of space and comfort during their stay. The suites feature air conditioning to keep things cool and pleasant no matter the weather. Whether you’re relaxing indoors or exploring nearby, this fantastic spot offers a welcoming retreat. Book now and enjoy everything this penthouse has to offer.

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$211.95

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Private Vacation Home

Quaint Islamorada Cottage with Unbeatable Location

Islamorada, Florida, United States

Escape to this quaint 2-bedroom, 1-bathroom conch-style cottage in the heart of Islamorada. The fully equipped kitchen and cozy living space invite you to feel right at home, while the Keys-style Florida room offers a breezy spot to soak up the beautiful winter weather.brbrUnwind in the private hot tub or lounge in one of the many outdoor seating areas, ideal for sipping your morning coffee or enjoying evening cocktails under the stars. With a spacious, fenced-in yard featuring lush, green grass, this cozy retreat is perfect for those seeking relaxation and tranquility.brbrLocated in an unbeatable downtown spot, you’ll be just a short stroll from the vibrant Morada Way Art District, filled with galleries, shops, and local charm. Whether you're here for adventure or a peaceful getaway, this cottage is your perfect home base.brbr28 night minimum. Please inquire for rates and availability.brbrKeys Cottage ~ MM81 Oceanside

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Exceptional(1)

$216.13

/ Nightly

Private Vacation Home

BEAUTIFUL PLACE TO STAY!

Islamorada, Florida, United States

ONE OF THE BEST vacation value getaways in the Florida Keys.br brPacked with amenities, access to gulf side dockage, a great park next door and has many other SUN & FUN activities in the area. brbrThis is considered the upper keys area and is very convenient to get to. brbrApproximately 1.5 hour drive from MIAMI airport. brbrThis is a gated community with 24 hour security, very private and exclusive for the residents. There's a very nice community pool and a club house.brbr***Please note: We have had 5 Star reviews on VRBO for the last 20 years! Due to our inactivity on VRBO (family using condo) our original account with all our reviews was deactivated and was required to make this new listing. Please check other rental platforms to see our stellar reviews! We promise you will LOVE this unit!***br brThe unit is very well maintained and can sleep up to 8 comfortably. There is a total of 3 full bedrooms and a loft on the 3rd floor. The unit will comfortably sleep 8! brbrThe unit is only about two hours from Key West and there are so many unique sights and sounds in the area. Most important though, is that you will experience the Florida Keys legendary lifestyle! brbrNo watches, no worries, everyone is laid back. Whatever you are into: boating fishing, snorkeling, diving, this rental is for you. brbrYou are assured a peaceful and relaxing vacation here. brbrOwners are very accommodating!!br

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$351.08

/ Nightly

Condo

Ocean Harbor Paradise in Islamorada

Islamorada, Florida, United States

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

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$455.63

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Private Vacation Home

Exclusive White Marlin Beach Retreat - Private Beach Access & Dock

Islamorada, Florida, United States

Your Islamorada waterfront getaway awaits at this charming three-bedroom home, offering comfortable accommodations with two queen beds, one full bed, and one twin bed. The home is fully air-conditioned and designed for relaxing after days spent on the water or exploring the Keys. Enjoy direct canal access with dockage for fishing boats, paddleboards, and kayaks, plus quick access to both the Atlantic Ocean and Florida Bay. A rare private sandy beach access adds an exceptional touch to this Islamorada property. Located in the heart of the Sportfishing Capital of the World, you’re just minutes from world-class offshore and backcountry fishing, snorkeling, diving, and renowned waterfront dining. Whether you’re planning a fishing trip, island escape, or laid-back beach vacation, this waterfront rental offers the ideal blend of comfort, convenience, and coastal beauty.

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$247.41

/ Nightly

Private Vacation Home

Beautiful Home located in Downtown Islamorada

Islamorada, Florida, United States

PROPERTY NAME: Mango Housebr81212 Old Highway Islamorada, FloridabrbrLocation: Ocean side located on the Old Road by Green Turtle RestaurantbrbrMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedbrbrMile Marker : 81brbrDetails: This home is absolutely beautiful with Keys local artist artwork everywhere, - Ocean side walking distance to the Iconic Green Turtle Restaurant, The property is Gated and Private, plenty of parking for your vehicles and boat trailer if needed. It features a beautiful pool with a shallow sitting area. When you walk in you are at home, the house is beautifully decorated with Local Artist Artwork through out. The living room has a pull out couch, and plenty of seating for the family, the kitchen is completely remodeled. You have 2 bedrooms and 2 baths. There is a front porch to sit and enjoy the beautiful surrounding lush trees. You also have a Porch in the backyard to sit and enjoy the pool area. The backyard features beautiful trees and shrubs for privacy while enjoying the Pool. If you are looking for Private and Quiet, this is the house.brbrSleeping Arrangements: Sleeps 4 comfortablybrPrimary Bedroom:brGuest Room:brbrAmenities Include: Heated Pool, Outdoor Seating, BBQ Grill, Private BackyardbrbrActivities: Beach, Swimming, Boating, Offshore Fishing, On shore fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours

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Exceptional(24)

$450.0

/ Nightly

Private Vacation Home

Islamorada retreat Bungalow Blue w/ heated pool, Bikes, BBQ, amenities galore!

Islamorada, Florida, United States

Welcome to paradise! Completely remodeled and immaculately maintained... Bungalow Blue is nestled away in the quiet quaint Shady Palms community of Islamorada MM76, Lower Matacumbe.brIf you're looking to relax and unwind while also being in close proximity to enjoy the best Islamorada has to offer, this is the place for you! brIdeally situated next to the community heated pool shared with only 6 other bungalows, down the street from the private boat ramp/dock, and surrounded by palm trees and tropical native landscaping, you'll truly feel you're in paradise.brEnjoy the Florida Keys lifestyle in the landscaped back yard, play a game of corn hole or jump on the beach cruisers for a short bike ride to Robbie's famous marina to feed the giant tarpon, water sport rentals, and enjoy drinks, food, and shopping.brHave your own boat(Under 26') Enjoy our free/no crowds boat launch providing direct access to the east coast waters.brbrBungalow Blue offers:br 2 bedrooms w/ queen bedsbr Newly updated bathbr New kitchen w/ stainless and granitebr Living roombr Washer/dryerbr Central A/Cbr High speed Internet & WiFibr 3X Smart Flat screen TV'sbr BBQbr Corn Hole and gamesbr 2X Beach Cruiser bikesbr Private boat rampbr Beach Chairs/Towelsbr Founders Park free accessbr Private yard w/ picnic table/Adirondack chairsbr Spacious new front porch w/ 2X umbrellas and chairsbr Hurricane impact windows and doorbrbrYou'll find a welcome packet upon arrival that includes recommendations for local dining and recreational activities. Islamorada, known as the Sportfishing Capital of the World, lends itself to some of the most famous marinas, including Bud & Mary's, only a 5 minute drive from your bungalow, and home to a fleet of charter boats and captains. brWhether you want to fish, snorkel, dive, kayak, paddle-board, or just take a cruise to the sand bar, there are multiple rental opportunities available in close range. 15 minutes north, you'll find Founders Park known as The Gem of Islamorada which offers outdoor recreation, tennis, aquatics, sports events, and a lovely beach for snorkeling(free access with copy of lease). Centrally located in the Keys allows you to day trip to Key West in 1.5 hours, or north to Key Largo in 45 minutes. Disclosure: there are two security cameras, one located on the exterior front porch and one on the back of the property solely for security purposes. brPlease feel free to reach out with any questions you may have as we are always here to help! We hope you will come visit and get to love Islamorada and our bungalow as much as we do!br- Yasmin & Joe Bartolomei

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Bed

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Sleeps

Vacation Rentals By Owner In Islamorada, FL

$254.99

$254.99

$277.57

$274.07

$1588.39

$278.64

$278.64

$195.92

$518.56

$2493.63

$369.28

$307.38

$4806.62

$562.5

$211.95

$216.13

$351.08

$455.63

$247.41

$450.0

Rent a place that suits your needs

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