Home Vacation Home Rentals By Owner In Islamorada, FL

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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.
Bed 7

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Bath 7

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Sleep 16

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Exceptional(16)

$375.64

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Private Vacation Home

Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families.

Islamorada, Florida, United States

The Lobster Home is a charming 2 bedroom, 2 bathroom oceanfront home located on the gated Alligator Reef property in Islamorada. Set just steps from the water, this home offers a relaxed Keys atmosphere perfect for a peaceful getaway.brbrGuests staying at Lobster enjoy access to the beautiful shared oceanfront grounds, including a sandy lounging area with a fire pit, an observation dock, and kayaks and paddleboards for exploring the clear waters.brbrComfortable and inviting, the Lobster House is ideal for a small family or couple looking to enjoy the beauty of the Florida Keys in a quiet waterfront setting.brbrFor larger groups or extended families, the nearby Conch House (3 bedroom, 2 bath) on the same property can also be reserved, allowing both homes to be booked together for a private oceanfront compound experience.brbrEnjoy the laid-back island lifestyle, ocean breezes, and endless views that make this special property a true Keys escape.brVACATION RENTAL LICENSE: 24-0389 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.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. 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 6

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Exceptional(17)

$630.38

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Private Vacation Home

GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS

Islamorada, Florida, United States

Contact owner for rates and availability at (305-431-2006).brRelax in Islamorada, Florida Keys... 'Sport Fishing Capital of the brWorld.' Enjoy deep blue water or back country fishing. Dive, brsnorkel, and swim on a clear, white, sandy beach (rare in the brKeys!). Walk/jog among beautiful waterfront homes. Sip wine while gazing at glorious sunsets while surrounded by coconut palms, Manatees, tarpon, mangrove snappers, and other native fish species. Swim the warm waters at our beach and fish off our dock. Beautiful tropical vegetation, shore brbirds, and other marine life are all around you. You will cherish brthe memories of your stay in this 'Island Paradise.' Islamorada Florida is known as 'The Purple Isle' and is located in the heart of the Florida Keys - midway between bustling Miami and laid-back Key West.brThis charming island home on a deep-water canal features high-beamed brceilings and a 'loft.' The walk-around deck, open floor plan, and brkitchen designed for entertaining make this home an excellent choice brfor a carefree vacation. The home is newly furnished and redecorated brand has two spacious bedrooms each with a private bath. The home is brequipped with High Speed Wireless Internet Access.brThe home's 70-foot boat dock gives easy bay and ocean access and the brprivate beach is a few steps away with its own private access.
Bed 2

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Bath 2

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Sleep 4

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Exceptional(38)

$393.46

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Private Vacation Home

LAST MINUTE MEMORIAL WEEK 300 a NIGHT SUMMER 2026 SPECIAL DISCOUNTED RATES

Islamorada, Florida, United States

Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located in an exclusive gated community of 50 island homes called Angler's Reef. The community includes a beautiful oceanfront pool, a private marina, and two stunning man-made beaches, a rarity in the Florida Keys. A famous sandbar amid turquoise waters is located right in front of the community and can be reached by kayak or boat.brbrOur island home is cleaned professionally and we maintain a non-smoking pet-free environment. The house sleeps four and has a Master bedroom with an en-suite Master bathroom and a large private balcony. The large second bedroom is also a master suite featuring an en-suite bathroom with a tub and a small private balcony. The living area includes a formal dining room and living room, as well as a modern open kitchen. A large queen sofa bed can accommodate two if more sleeping space is needed. A large private porch amid lush tropical gardens with BBQ and white wood rocking chairs. The house is tastefully decorated and equipped for all your needs to enjoy a perfect vacation.brbrOur village offers restaurants for all tastes and prices as well as fun adventures for singles, couples and families. We have numerous unique boutiques and shops, where you can also find rare items. But most important is that you will have the time of your life in our beautiful place in Angler's Reef!brbrNote: Children welcome, non smoking only, pets not allowed, wheelchair inaccesible
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(67)

$630.38

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Private Vacation Home

GREAT LOCATION !!! White Marlin Beach House, Islamorada

Islamorada, Florida, United States

Contact owner for rates and availability (305-431-2006).brRelax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' Enjoy deep blue water or back country fishing. Dive, snorkel, and swim on a clear, white, sandy beach (rare in the Keys!). Walk/jog among beautiful waterfront homes. Sip wine while gazing at glorious sunsets while surrounded by coconut palms.brbrManatees, tarpon, mangrove snappers, and other native fish species swim the waters off our dock. Beautiful tropical vegetation, shore birds, and other marine life are all around you. You will cherish the memories of your stay in this 'Island Paradise.' Islamorada is known as 'The Purple Isle' and is located in the heart of the Florida Keys - midway between bustling Miami and laid-back Key West.brbrThis charming island home on a deep-water canal features high-beamed ceilings and a 'loft.' The walk-around deck, open floor plan, and kitchen designed for entertaining make this home an excellent choice for a carefree vacation. The home is newly furnished and redecorated and has two spacious bedrooms each with a private bath. The home is equipped with High Speed Wireless Internet Access.brbrThe home's 70-foot boat dock gives easy bay and ocean access and the private beach is a few steps away with your own private access.brbrKeywords: Beach House
Bed 2

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Bath 2

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Sleep 5

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Exceptional(117)

$602.67

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Private Vacation Home

Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip

Islamorada, Florida, United States

Welcome Back!! I temporarily took the property off the market during COVID and for renovations. I am looking forward to having my returning guest come back and visit.brPlease look at the (video icon) in the picture to view the video of the homes location. A tropical boater's and angler's paradise, this Key West styled luxury villa in Islamorada boasts the best fishing in South Florida. With tangerine sunsets glistening across the calm ocean waters, an afternoon boat ride is as easy as walking out your back door. Dolphin and turtles are common. Deep water access, boat dock, nearby marina with fuel, bait and tackle shop, nearby waterfront restaurants and short boat ride (seen from the balcony) to the famous sand bar located behind Holiday Isle weekend hot spot.brbrThis is the developer unit with the largest fully equipped kitchen in the development. Large living room with a beautiful view of the ocean, 3 BR's, den, 2 1/2 luxury baths, sleeps 10 comfortably. Wood floors, glass designer tile throughout, california closets, covered parking with an additional parking spot. Upper and lower decks overlook ocean view. Flat screen TV's, cable, internet service. (Kitchen utensils, dishes and linens are plentiful). Security gate for privacy and peace of mindbrbrCommunity pool and dock space with electric and water hook-up.brbrNote: I also have a 2-bedroom rental home in Anglers Reef neighborhood with a boat dock included. VRBO Listing 3578196brbrKeywords: Breath taking views. Sunrise in the morning on the back balcony. Deep water access to a private dock. View of the Pool. Very relaxing.
Bed 4

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Bath 2

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Sleep 8

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Exceptional(118)

$774.94

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Private Vacation Home

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

Islamorada, Florida, United States

Angler's Reef is located at MM85 in Islamorada, the heart of the Florida Keys. Our gated community is made up of 52 luxury waterfront villas accompanied by a boat basin with 36 slips, and a pool among the many amenities.brbrEnjoy the expansive views and ocean breezes from the wrap around balconies on the first and second story. Fully remodeled chef's kitchen with top of the line appliances, quartzite counters, eat at bar, large pantry and extra beverage/bar fridge. Kitchen is fully stocked with cookware, dishes and appliances. Gas grill outside. Starter toilet paper and paper towels, basic cleaning items, drip and Keurig coffee makers, and basic spices in kitchen are included.brbrOne bedroom downstairs with queen bed and ensuite bath. Upstairs bedroom #1 has a queen bed. Upstairs bedroom #2 has 2 full beds. Hall bath and washer/dryer upstairs. Primary bedroom upstairs has king bed, private bath and amazing wrap around porch. Linens, bath towels and beach towels are all provided and replaced often.brbrBoat slip fits boat up to 31ft and is included with your rental. The community also provides kayaks for your enjoyment (first come/first served). No trailer parking onsite.brbrSmart TV to log in to your favorite streaming services, wifi, board games, some childrens' toys provided. Highchair and pack n' play for our littlest guests. brbrPictures and description are representative of accommodations provided but are subject to change. brbrNo pets allowed! Service animals will be accommodated but prior notice and HOA approval is needed. Please contact owner PRIOR to arrival for accommodation. brbrLicense #VR-226
Bed 4

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Bath 3

Bath

Sleep 8

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$237.86

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Private Vacation Home

Executive Bay Club R8 ~ 3 Bed / 3 Bath + Loft Townhouse on Plantation Key

Islamorada, Florida, United States

Discover your ideal getaway at this charming seascape in Islamorada! This lovely 3-bedroom, 3-bathroom townhome, complete with an additional loft, accommodates up to 10 guests. With ample amenities to keep you busy such as pickleball, tennis, pool, and beach you’ll be ready to spend your days soaking up the sun and salty air at this bay-side retreat.brbrAs you enter, you'll find a contemporary kitchen outfitted with stainless steel appliances and a coffee bar. The open layout seamlessly connects the kitchen, dining area, and living space, making it great for gatherings. The main floor also features a laundry area, a full bath, and a back patio equipped with a grill. Venture upstairs to discover a master suite with a king-size bed and en-suite bathroom. There are two more guest bedroom, one with a queen bed, and another with a full size bunk and twin size bunk— both sharing a full bath. Additionally, this floor offers a loft with two twin beds, accessible via a ladder. brbrExecutive Bay Club is conveniently located next to Founder's Park, which features an Olympic-sized swimming pool, a children's splash pad, a beach, picnic areas, playgrounds, fitness and walking trails, a basketball court, soccer fields, baseball diamonds, pickleball courts, and a golf driving cage. If you require docking facilities, Plantation Yacht Harbor Marina boasts secure marina access with 80 boat slips available for daily, weekly, monthly, or annual rental. Amenities at the marina include electric, water, sewage pump-out, and fuel sales, along with a boat ramp and dedicated trailer parking. You'll also be just a short distance from some of the best dining and attractions in the Keys, including Marker 88, MEAT Eatery and Taproom, and Rain Barrel Village.brbrAt Executive Bay Club, the activities are endless. The pool and clubhouse were fully remodeled in summer 2025, offering fresh, modern accommodations for guests to enjoy. Spend the day lounging at the private beach, cool off in the sparkling pool, play a round of tennis, or take a sunset stroll to the end of the dock. 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.
Bed 4

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Bath 3

Bath

Sleep 10

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Exceptional(75)

$573.55

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Private Vacation Home

Boat, Fish, Swim from Your Own 70' Dock!

Islamorada, Florida, United States

Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing under the shady, palm-roof “Chickee.” Enjoy your privacy with independent upstairs/downstairs units - friends, family, or guests will appreciate the extra bed, bath, living room and refrigerator downstairs.brThe Dock: Have your boats or yacht waiting just outside your door. Large, deep-draft sailboats or yachts are easily accommodated with a waterway 20 ft deep and 100 foot wide. Even tall vessels travel quickly between the Ocean and Florida Bay using the drawbridge just 1000 yards from the dock. With gas, bait, and tackle shops located before the bridge, your convenience is assured. br*****Love Fishing ***** Enjoy casting right from the dock for yellow tail, red snapper or grouper. Cast-offshore for sport fishing in the Gulf Stream. The world famous “hump,” an underwater mountain just 11 miles from the dock, has made Islamorada fishing world famous; catch marlin, sailfish, black-fin tuna, mahi-mahi, wahoo and many more ocean treasures.brbrOr just as easily, go backcountry fishing in Florida Bay and catch speckled trout or tarpon. A fish cleaning station at the end of the dock lets you clean your catch whenever your reeling arm is rested and ready.brbr*****Love Swimming, Snorkeling or Diving ***** Enjoy endless swimming right from the dock where the water is clean and refreshing, and the beverages are never far away. Living reefs and sunken wrecks are easily enjoyed by everyone, just three miles from the dock in 3-15 ft of water. Enjoy colorful tropical fish, coral rock formations and sea fans. Certified divers will enjoy the drop-off just five miles out, where the 20-30 foot reefs transition to 60+ feet, and sea life changes. And the world famous Islamorada Sandbar is just a 10 minute boat ride away for the daily water social.br brThe House: We only rent the house to one party at a time – so the upstairs and downstairs units are yours! Upstairs has Two Bedrooms, with a king size bed in the Master, a queen in the other guest suite, and a queen size sofabed in the living room There is one Bathroom upstairs and one downstairs. Downstairs has one Bedroom with a king size bed and a queen size sofa bed. Enjoy the convenience of a first floor bathroom, and refrigerator, sink and Microwave – perfect for those lazy outside days!brbrEnsure everyone's comfort with separate air conditioning systems for the upstairs and downstairs. You’ll find all of the conveniences you expect – comfortable accommodations, fresh linens, plenty of kitchen utensils, laundry machines, and a gas barbeque grill.brbrYou will also find some unique conveniences, like plenty of room to park your boat trailer, extra dock capacity next door, an open lot next door for unobstructed breezes, a shaded palm-roof “chickee”, and private fish cleaning station. There are hanging chairs and a plush hammock for enjoying the outdoor experience... In all, there is room to stretch out and relax without being crowded by others.brbrFounders Park is 3000 feet from the house: an easy walk or drive, where you can enter free with your rental contract and enjoy the beach, walking paths, and family playgrounds. They provide small-fee access to swimming in the Olympic size pool - complete with diving boards, lap-lanes, and a separate splashpad for kids. Founders park is convenient for launching/loading boats at the boat ramp for nominal fees ($3/person pool, $20/ launch or loading boats). Larger boats are recommended to put in at the Harry Harris boat Ramp at mile marker 92.5 - just 6.5 miles from your rental & dock for the week.brbrCome and stay. Upstairs or down– this is a great place to play.brbrKeywords: Waterfront Home
Bed 4

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Bath 2

Bath

Sleep 6

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