Home Vacation Rentals By Owner In Islamorada, FL

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Exceptional(2)

$804.35

/ Nightly
Private Vacation Home

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Islamorada, Florida, United States

Experience waterfront FL Keys living at its finest at The Seascape, a modern, newly constructed retreat nestled directly on the ocean where every morning begins in color, and every evening ends in calm. Here, the ocean isn’t just a view. It’s a presence. Come make memories at Islamorada's iconic tiki bar sandbar, legendary fishery, or gather on sunlit shores to relax and revel in life’s simplest joys with stunning views, direct water access, and a stylish escape from the everyday.brbrLocated in a secure, gated enclave, The Seascape provides one of the closest waterfront experiences available in the Florida Keys, complete with private dockage and sweeping ocean views. Spanning over 2,000 square feet, this spacious three-bedroom residence boasts two expansive oceanview balconies, a private exclusive entertainment lounge, and interiors curated for both relaxation and refined living. Whether you’re planning a family vacation or a retreat with friends, The Seascape is your launch point for making lifelong memories. Keep your eyes open for dolphins, manatees, and pelicans, or gaze across the water toward the iconic Alligator Reef Lighthouse and Islamorada Sandbar.brbrStylish Interiors with the Comforts of Home in MindbrThe Seascape was designed for both relaxation and entertainment, featuring:br✔ Two large balconies overlooking the ocean—perfect for outdoor dining, a morning coffee or an evening glass of winebr✔ A fully stocked designer kitchen with stainless steel KitchenAid appliancesbr✔ A bright living area with oversized sectional seating and a 65 OLED 4K TVbr✔ Thoughtful details and elegant decor throughout every roombrbrThree Private Tranquil Bedrooms with Room for Everyonebr✔ Primary Suite – King bed, private patio that extends the bedroom to the ocean front with comfortable egg chairs, and ensuite bath with a walk-in rainfall shower br✔ Second Bedroom – King bed with ensuite bath with a walk-in rainfall shower br✔ Third Bedroom – Ideal for kids or additional guests, featuring a full-size bunk bed with a pull-out trundle and ensuite bath with a walk-in rainfall showerbrbrBonus Entertainment Space – Exclusive to This HomebrUnwind in your private lower-level entertainment retreat, complete with:br✔ 55 4K Smart TV with gaming systembr✔ Ping pong table, pop a shot, mini-putt matt, board games, books, and morebr✔ Lounge area with sectional seating and bean bagsbr✔ Outdoor games like cornhole for fun in the sunbrbrPool, Private Dockage & Water Gear Includedbr✔ Dock space for boats up to 26 ft (advance reservation required)br✔ Kayaks and paddleboards available for guest usebr✔ Enjoy the community’s heated oceanfront pool with lounge chairs and a sun shelfbr*Options for nearby trailer storage will be provided since we cannot accommodate trailers onsite.brbrNearby Attractions Include:br✔ Feed the tarpon at Robbie’s Marinabr✔ Visit dolphins and sea lions at the walkable Theater of the Seabr✔ Snorkel vibrant coral reefs and local shipwrecksbr✔ Offshore fishing charters at nearby Bud n Mary's and whale Harbor marina to best enjoy the sportfishing capital of the worldbr✔ Relax at Islamorada Library Beach or Founders Park (free guest access!)br✔ Explore the charming shops and galleries of Morada WaybrbrThis awesome home comes with AC, a washing machine, WiFi, heating, and even a fitness room. With 3 bathrooms and a hair dryer, guests will have everything they need for a comfortable stay. Our place is equipped for both long or short stays to make your holiday one to remember.
Bed 3

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Bath 3

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Sleep 8

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$649.41

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Cottage

Lush tropical plantings in a gated compound located directly on the Florida Bay

Islamorada, Florida, United States

PROPERTY NAME: Little Bay Cottagebr82246 Overseas Highway, Islamorada, FloridabrbrLOCATION: Cottage located directly on the Florida BaybrbrMINIMUM STAY: Weekly or MonthlybrbrMILE MARKER: 82.2brbrDETAILS: br- Located on a one-acre lush tropical setting in a gated compound directly on Florida Baybr- One of 3 separate units for rent by the week or month, each sleeping up to 6 peoplebr- Protected dockage for up to a 34-foot boatbr- Sunning area with lounge chairs on the peninsulabr- Hammocks, pergola, and tiki for relaxingbr- Panoramic views of Florida Bay from the covered balconybr- Spacious interior with 2 bedrooms, 2 bathrooms, and a queen-size sleeper sofabr- Updated kitchen with new appliances and granite countertopsbrbrLittle Bay's Cottage is a ground-floor home with a unique floor plan. The main living area is in the center of the house, with a kitchen, dining area, sitting area, and full bathroom. To the right is a large bedroom with a king bed and full bathroom. The laundry area with a full-size washer and dryer is also located in this room. To the left of the living area is an enclosed sunroom that can be used as a second bedroom at night. The sofa in the sunroom converts to a queen-size sleeper, and there is also a twin-size Murphy bed. The cottage offers a little more privacy than the duplex units, but it does not have water views.brbrThe three units are available for rent by the week or month. Each unit sleeps up to 6 people, so you can rent one or all of them for a family reunion. Protected dockage in the little bay can accommodate boats up to 34 feet long. There is also a sunning area with lounge chairs on the peninsula, as well as hammocks, a pergola, and a tiki hut. All of the units have central air conditioning, a flat-screen TV in the living room, and WiFi. brbrSLEEPING ARRANGEMENTS: Sleeps 6 comfortablybrPrimary Bedroom: King Bed, Bathroom with Shower brGuest Bedroom: Queen Sleeper Sofa and Twin Murphy Bed, Bathroom with showerbrbrAMENITIES INCLUDE: Dockage for up to a 34 ft boat, Charcoal grill, Hammocks, Pergola, Swim and Snorkel in the bay. There is also Cable TV, WiFi, washer and dryer, air conditioning and free parking. brbrACTIVITIES: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures. Near by, there is John Pennekamp Coral Reef State Park, Theater of the Sea, Robbie's Marina and Islamorada Fishing Pier.brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family.
Bed 1

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Bath 2

Bath

Sleep 4

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$1493.98

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Villa

Deactivated due to Bad Review and Low Productivity compared to other listings.

Islamorada, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
Bed 4

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Bath 2

Bath

Sleep 12

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$740.51

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Private Vacation Home

Luxury Waterfront Escape- Brand New Home In Venetian Shores

Islamorada, Florida, United States

Welcome to 104 Leoni Drive, a stunning new home in the highly sought-after Venetian Shores neighborhood of Islamorada. This 4-bedroom retreat has it all—a private pool, deepwater dockage, and a prime waterfront location with easy access to both the Ocean and Florida Bay.brbrStep inside, and you'll immediately feel at home. The open-concept living area is bright, airy, and beautifully designed, with high-end finishes and plenty of natural light. The gourmet kitchen has everything you need to whip up meals after a day on the water, and the spacious living room is perfect for unwinding in the evenings.brbrEach bedroom is thoughtfully designed for comfort, with plush bedding and stylish touches. The primary suite is a true retreat, featuring a private balcony with incredible waterfront views—the perfect spot for your morning coffee or an evening cocktail.brbrOutside, the pool invites you to soak up the Florida sun, while the private dock makes it easy to head out for a day of boating, fishing, or just relaxing by the water. With deepwater access via Snake Creek, you'll be on the ocean or bay in no time.brbrLocated in one of the best neighborhoods in Islamorada, you're just minutes from great restaurants, shopping, and all the fun the Keys have to offer. Whether you're here for adventure or just to kick back and relax, this home is the perfect place to do it all.brbrBook your stay today and experience the best of waterfront living 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.
Bed 4

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Bath 3

Bath

Sleep 8

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$461.63

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Private Vacation Home

Cozy Islamorada retreat!

Islamorada, Florida, United States

Our Islamorada home is your home away from home! Our home is in a private and quiet, gated community on the bay side, with only 16 other homes, on MM 83. We have a private marina, with a dedicated boat slip for each home; our home is only 3 homes away from the marina. Our backyard is a tropical oasis! We have 2 in pool loungers, 4 tanning beds/chaise loungers, sitting area equipped with a sofa and 2 individual chairs, for hanging out. Our outdoor kitchen is equipped with it all! Seating for 11, built in bbq, side burner, 2 refrigerators, an ice maker and a sink. We really enjoy making a nice fish fry on the outdoor side burner, so that the home doesn't stink up! Let's not forget about the outdoor fire pit, with oolite rock seating, surrounding the fire pit. If you don't want to make smore's, feel free to lay on the hammock, while you watch your family/friends get warm during the cooler nights. Our dining room, which seats 8, is screened in, which makes for beautiful mornings and evenings; have your coffee while listening to the birds chirping and enjoy a nice dinner on chilly nights (60-70 F). Our home is close to many restaurants in Islamorada and behind Publix supermarket, which is convenient! Let's not forget to mention that our beds are Casper brand and, comfortable!brbrWe are close to the following restaurants: Ziggie & Mad Dogs, Chef Michaels, Island Grill, Whale Harbour, Mangrove Mikes, Islamorada Fish Company, Pierre's, Morada Bay, Marker 88, Lorelei, Cia Hound Italian Kitchen & Bar, Square Grouper, Bayside Gourmet, Midway Cafe, Bobs Bunz, Off the hook churrascaria, and many more!!
Bed 4

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Bath 2

Bath

Sleep 8

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$248.47

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Condo

Discover Futura Yacht Club 503 in Islamorada—your perfect 2-bedroom retreat!

Islamorada, Florida, United States

Now available for rent!brThis highly desirable Futura Yacht Club condo offers the perfect blend of comfort and convenience in the Florida Keys. Featuring 2 spacious bedrooms and 2 bathrooms, this residence provides an ideal retreat whether you're here full-time or seasonally.brHighlights:brBoat slip included — bring your vessel and enjoy easy access to the waterbrResort-style amenities including pool, tennis, and clubhousebrGated community for added privacy and securitybrPrime Islamorada location close to shopping, dining, and world-class fishingbrDon't miss this opportunity to rent at one of Islamorada's most sought-after communities!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.
Bed 2

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Bath 2

Bath

Sleep 4

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$2562.14

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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.
Bed 7

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Bath 7

Bath

Sleep 16

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Exceptional(8)

$508.35

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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!
Bed 4

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Bath 4

Bath

Sleep 8

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Exceptional(3)

$1588.39

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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 #: 25-0147 - Islamorada
Bed 2

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Bath 2

Bath

Sleep 4

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$341.07

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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
Bed 2

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Bath 2

Bath

Sleep 5

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Home Most popular vacation rentals in Islamorada