Vacation Home Rentals in Islamorada, Florida

Vacation Home Rentals in Islamorada, Florida

Chesapeake Resort
Vacation rental
0.2 miles to Islamorada
Islamorada, 33036
Chesapeake Resort in Islamorada, Fla., boasts an oceanfront location in the Florida Keys. This region is world-famous for fishing, diving and...

from 1,778 USD

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Dream Home in the Keys
Vacation rental
0.2 miles to Islamorada
Islamorada, 33036
Very private, very large, home in Islamorada with heated pool and 120 foot of deep water dockage.
Ocean Pointe Suites at Key Largo
Vacation rental
7.7 miles to Islamorada
Islamorada, 33070
Location. The Ocean Pointe Suites at Key Largo, Fla., is less than seven miles from Dolphins Plus where visitors can swim with dolphins. John...

from 1,323 USD

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Vacation rental
0.2 miles to Islamorada
Islamorada, 33036
Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport...

from 2,125 USD

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House with 3 bedroom(s), 4 bathrooms(s), sleeps 6
Islamorada, Florida, 33130
Designers home located in Venetian Shores, mm86. 70ft dock space on a clean, deep water canal that leads to Snake creek where there is acess to...

from 257 USD

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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 8
0.2 miles to Islamorada
Islamorada, Florida, 33036
Beautiful, bayside townhome located on Mile Marker 87.2 (bayside) in the heart of Islamorada, 'The Fishing Capital of the World.' Two Bedroom, Two...

from 214 USD

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House with 2 bedroom(s), 2 bathrooms(s), sleeps 7
7.7 miles to Islamorada
Islamorada, Florida, 33070
Come experience Florida Keys paradise. Stay in this two bedroom two bath home that sits on a bay side canal located on Islamorada Key. The...

from 200 USD

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House with 4 bedroom(s), 4 bathrooms(s), sleeps 12
7.7 miles to Islamorada
Islamorada, Florida, 33070
Casa Eroici, is a 4 Bedroom 4 ½ bath estate, nestled in 2 acres of gated, prime landscaped grounds in a premier area of Islamorada Florida also...

from 1,071 USD

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House with 10 bedroom(s), 6 bathrooms(s), sleeps 20
0.2 miles to Islamorada
Islamorada, Florida, 33036
The Florida Keys Largest, most Prestigious Vacation Rental Home Available Vacation in your own private Oceanfront Mansion in the Florida Keys ...

from 1,714 USD

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Condo with 3 bedroom(s), 2 bathrooms(s), sleeps 5
0.2 miles to Islamorada
islamorada, Florida, 33036
Beautiful new Bay Harbour gated condo community on lower Matecumbe, mm74 1/2. Incredible amenities include : - New heated pool and jaquzzi. ...
Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 6
0.2 miles to Islamorada
islamorada, Florida, 33036
ON the water just look AT the pictures When you walk in you will feel like you are right on top the water. WE have IT ALL...Just Bring...

from 214 USD

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Condo with 3 bedroom(s), 2 bathrooms(s), sleeps 8
0.2 miles to Islamorada
Islamorada, Florida, 33036
Gorgeous new Bay Harbour gated condo community on Lower Matecumbe, MM 74 1/2.Lush tropical landscaping,heated pool with jetted spa,two lighted...

from 300 USD

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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 4
0.2 miles to Islamorada
Islamorada, Florida, 33036
Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains...
House with 2 bedroom(s), 2 bathrooms(s), sleeps 6
0.2 miles to Islamorada
Islamorada, Florida, 33036
Luxurious ten unit oceanfront complex on Millionaires Row, Plantation Key, Islamorada, MM 88. Units built in 1994.360 degrees water views from...

from 250 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 10
0.2 miles to Islamorada
Islamorada, Florida, 33036
Piece of Paradise in Islamorada Home is perfect for everyone wanting to vacation in the Florida Keys without having to spend a fortune doing so....
House with 5 bedroom(s), 4 bathrooms(s), sleeps 13
0.2 miles to Islamorada
islamorada, Florida, 33036
Southern Diversion is in the heart of beautiful Islamorada in the Florida Keys. This is an exclusive oceanfront private gated estate home with...

from 714 USD

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Vacation rental with 2 bedroom(s), 2 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Vacation in beautiful peaceful Islamorada, in the Florida Keys. Islamorada, "Fishing Capital of the World". Bayside access Townhouse is a newly...
Vacation rental with 2 bedroom(s), 2 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
Enjoy the spacious ocean front beach condo . Two luxurious bedrooms and two baths . Luxurious master size bedroom offers a king size bed &...

from 150 USD


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Vacation rental with 3 bedroom(s), 3 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. 100' of dock less than two...
Vacation rental with 4 bedroom(s), 3 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
The Great Islamorada Getaway features a spectacular canal front home on an over-sized property with 136 feet of dock space and an in ground pool. ...

from 414 USD


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House with 4 bedroom(s), 3 bathrooms(s), sleeps 10
0.2 miles to Islamorada
Islamorada, Florida, 33036
This beautiful 4 bedroom/ 3 bath waterfront home is located in one of the finest neighborhoods of Islamorada- Venetian Shores. It is just 1...
Vacation rental with 3 bedroom(s), 2 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
Choose between two seperate suites (2bed/lbath $900) or (1bed/1bath $800) or BOTH combined for $1500. The upstairs (The Lighhouse Suite) is on...

from 214 USD


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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 4
0.2 miles to Islamorada
Islamorada, Florida, 33036
2 BR 2 Bath Modern décor with balcony. Large Master Bedroom with King sized bed and ocean view. Eat in Kitchen and Breakfast bar. 1...

from 103 USD

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Vacation rental with 2 bedroom(s), 2 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
Beautiful panoramic ocean views from every room in this direct oceanfront, bright and tastefully decorated and clean 1,200 sq. ft. end unit on the...

from 144 USD


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Vacation rental with 3 bedroom(s), 2 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Beautiful newer stilt home, 3 bedroom, 2.5 baths, enclosed pool and hot tub, end of street, very private on lake/canal looking over sanctuary,...
House with 3 bedroom(s), 2 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
Sun, Fun, No Problems MON! Relaxing times await you at our beautiful home in the keys. This beautiful home in prestigious Port Antigua sits on a...

from 1,495 USD

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Townhome with 2 bedroom(s), 1.5 bathrooms(s), sleeps 6
6.8 miles to Islamorada
Islamorada, 33036
This very clean and nicely decorated, newly renovated townhouse is located on the bay side in the heart of Islamorada on mile marker 76. Just...

from 1,200 USD

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Apartment with 1 bedroom(s), 1 bathrooms(s), sleeps 2
7.8 miles to Islamorada
Islamorada, 33036
The apartment is situated on the Gulf side of Lower Matecumbe Key in Islamorada. There is deep water dockage for your boat right outside your...

from 500 USD

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Cottage with 1 bedroom(s), 1 bathrooms(s), sleeps 4
5.8 miles to Islamorada
Islamorada, 33036
Shady Palms is a private residence which is newly remodeled, professionally decorated and wonderfully maintained. This Non-Smoking home is cleaned...

from 700 USD

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Villa with 5 bedroom(s), 3 bathrooms(s), sleeps 10
3.9 miles to Islamorada
Islamorada, 33036
Magnificent 4 bedroom house (sleeps 10) 3 bath, waterfront property located in Venetian Shores, the most prestigious subdivision of Islamorada,...

from 1,500 USD

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House with 5 bedroom(s), 5 bathrooms(s), sleeps 14
3.4 miles to Islamorada
Islamorada, 33036
Stunning bay view home in venetian shores. 100 ft. Of deep water dockage. Access the ocean or the bay in minutes via snake creek. Boat davits and...
House with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
3 miles to Islamorada
Islamorada, 33036
This Coastal Conch Style Cottage has recently been updated to accommodate vacation renters and their families. This Cottage has all new...

from 1,200 USD

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Townhome with 2 bedroom(s), 2.5 bathrooms(s), sleeps 4
0.3 miles to Islamorada
Islamorada, 33036
This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 51 homes . Quaint streets & walking paths wind through this...

from 1,400 USD

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Condo with 1 bedroom(s), 1 bathrooms(s), sleeps 4
5.8 miles to Islamorada
Islamorada, 33070
Enjoy spectacular sunsets and the blue-green waters of the Florida Keys! Come to relax or come to play! Take advantage of great snorkeling and...

from 650 USD

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Condo with 2 bedroom(s), 1.5 bathrooms(s), sleeps 6
0.7 miles to Islamorada
Islamorada, 33036
This Condo is exactly what you have been waiting for! Each room offers a total relaxing Island feel. French doors lead from the living room into...
Condo with 1 bedroom(s), 2 bathrooms(s), sleeps 4
0.3 miles to Islamorada
Islamorada, 33036
The Osprey Nest is a private residence which is wonderfully maintained. This Non-Smoking home is professionally cleaned prior to your arrival. The...

from 1,195 USD

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Condo with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
7.8 miles to Islamorada
Islamorada, 33036
Bay Harbor Beauty has a fabulous ocean view. Wake up to fabulous sunrises in this brand new two bedroom, two and-a-half bath condominium that...

from 750 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 9
3.4 miles to Islamorada
Islamorada, 33036
Transport yourself to a place of utter relaxation where the sun and surf will melt your worries away... This family home, with its open floor...

from 5,000 USD

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House with 4 bedroom(s), 4 bathrooms(s), sleeps 10
Islamorada, 33036
Spend a vacation in Islamorada in private, secluded luxury at Keys Villa Retreat. With a heated private pool and unrestricted view of the Florida...

from 18,000 USD

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Condo with 1 bedroom(s), 2 bathrooms(s), sleeps 4
0.4 miles to Islamorada
Islamorada, 33036
Holzman’s Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on...

from 1,295 USD

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Villa with 2 bedroom(s), 1 bathrooms(s), sleeps 5
1.2 miles to Islamorada
Islamorada, 33036
This is a wonderful 2 bedroom house with a full kitchen, living room, dining room and washer and dryer. The full bath has a large soaking tub and...

from 5,075 USD

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Condo with 3 bedroom(s), 2 bathrooms(s), sleeps 7
5.8 miles to Islamorada
Islamorada, 33070
Quiet gated community at mile marker 88.5 bayside in Islamorada with world class fishing and diving,2 lighted tennis courts, large heated pool,...

from 950 USD

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House with 4 bedroom(s), 3.5 bathrooms(s), sleeps 9
3 miles to Islamorada
Islamorada, 33036
Welcome to our lovely 4 bedroom 31/2 bathroom home in Islamorada here in the Florida Keys. Often promoted as the Sport-fishing Capitol of the...

from 3,800 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 9
7.8 miles to Islamorada
Islamorada, 33026
This home is the perfect getaway in the Florida Keys, brand new home in the fishing capital of the Islamorada Key, situated in the exclusive...

from 2,700 USD

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Condo with 2 bedroom(s), 2.5 bathrooms(s), sleeps 5
7.8 miles to Islamorada
Islamorada, 33036
Newly redecorated unit on the top floor (there is an elevator) offers great views of the bay and ocean beyond. Enjoy tropical breezes on the...

from 1,400 USD

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Condo with 3 bedroom(s), 2.5 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps...

from 1,700 USD

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Apartment with 3 bedroom(s), 2.5 bathrooms(s), sleeps 5
7.8 miles to Islamorada
Islamorada, 33036
Beautiful new Bay Harbour gated condo community on lower Matecumbe, mm74 1/2. Enjoy the sunrise or sunset from the balcony of this brand new 3...

from 2,300 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
This beautiful new home is furnished with a TV in each bedroom. Granite countertops in kitchen and bathrooms with stailess steel appliances....
Condo with 2 bedroom(s), 1.5 bathrooms(s), sleeps 6
5.3 miles to Islamorada
islamorada, 33036
This ISLAMORADA GEM is CLOSE TO everything. Whether it's fishing, diving, or shopping. This stylish Waterfront CONDO includes A Fishing Pier ON...

from 2,250 USD

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House with 4 bedroom(s), 4 bathrooms(s), sleeps 8
5.8 miles to Islamorada
Islamorada, 33036
Ocean front executive retreat with overwhelming views of the Atlantic, large open verandas, 165 feet of private sandy beach, 15 x 30 seaside...

from 4,800 USD

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House with 3 bedroom(s), sleeps 6
8.7 miles to Islamorada
Islamorada, 33036
Relax in our pristine Islamorada vacation rental canal front home with 70' of concrete dock and fish cleaning station. Located on Mile Marker...

from 1,600 USD

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House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
7.8 miles to Islamorada
Islamorada, 33036
Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the king, queen, and 2...

from 1,300 USD

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House with 3 bedroom(s), sleeps 6
0.3 miles to Islamorada
ISLAMORADA, 33036
Come Play! Your 70-foot dock provides instant access to fun – whether boating, fishing, swimming or relaxing under the shady, palm-roof “Chickee.”...
House with 3 bedroom(s), 3 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
This duplex located on wide lagoon with a view of the ocean. Has a private dock and deep water access via canals. Rental includes access to the...

from 2,500 USD

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Condo with 3 bedroom(s), 2 bathrooms(s), sleeps 6
6.2 miles to Islamorada
Islamorada, 33036
Start your day with a refreshing plunge in the sparkling pool or an an invigorating game of tennis. Here you can pamper yourself in the sun on the...

from 1,050 USD

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House with 2 bedroom(s), 2 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33036
Love the glorious views of the pristine waters of the Atlantic Ocean from every level of this Lower Matecumbe Key home. This beautiful canal-front...

from 1,800 USD

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Lodge with 4 bedroom(s), 3 bathrooms(s), sleeps 8
0.3 miles to Islamorada
Islamorada, 33036
The Royal Palm, South - Ocean Front Home Inspired by owner Phil Sena - with nothing compromised - this luxurious Caribbean home is on the ocean's...

from 1,500 USD

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Townhome with 2 bedroom(s), 2 bathrooms(s), sleeps 8
4.4 miles to Islamorada
Islamorada, 33036
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of Islamorada. Located within...

from 1,400 USD

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House with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
7.6 miles to Islamorada
Islamorada, 33036
The home features wood floors, stainless steel appliances, granite counter tops, ocean view, outdoor gas grill and offstreet parking. The home is...

from 1,800 USD

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Yacht with 2 bedroom(s), 2 bathrooms(s), sleeps 4
4.4 miles to Islamorada
Islamorada, 33036
TIRELESS is a beautiful, Classic Trumpy motoryacht that was built for Roger Firestone in 1963. The boat offers all of the modern conveniences...

from 8,500 USD

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House with 4 bedroom(s), 4 bathrooms(s), sleeps 12
2.1 miles to Islamorada
Islamorada, 33036
A large and comfortable luxury home with its own ocean side private beach, located in Islamorada, FL. The ocean can be seen from almost anywhere...
House with 2 bedroom(s), 1 bathrooms(s), sleeps 7
7.8 miles to Islamorada
Islamorada, 33036
The home is located in Islamorada, Florida in the beautiful Florida Keys at mile marker 74. As a reference, the south end of Miami is mile...

from 2,500 USD

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House with 2 bedroom(s), 1 bathrooms(s), sleeps 6
7.3 miles to Islamorada
islamorada, 33036
We have great back country fishing; the best tarpon fishing in the U.S. Charters just a couple of miles away. Escape to Key West spend the day...

from 2,700 USD

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House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
7.8 miles to Islamorada
Islamorada, 33036
Welcome: Yearly rentals available. Welcome to your paradise home in Islamorada. Whether you're an avid fisherman, diver, naturalist or just here...

from 2,300 USD

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House with 4 bedroom(s), 4 bathrooms(s), sleeps 10
3.4 miles to Islamorada
Islamorada, 33036
Plan your Keys Getaway to this elegant, spacious waterfront home with swimming pool, Jacuzzi and dock. Enjoy unforgettable sunsets while...

from 6,000 USD

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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 4
4.4 miles to Islamorada
Islamorada, 33036
Come to Paradise and Enjoy it with Luxury, Comfort, and Style! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of...

from 2,300 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
Islamorada is the fishing capital of the world! Renowned for Tarpon, Sailfish, Bone Fish, Canoeing, Wind Surfing, Lobster and reef fish, Dolphin...

from 2,000 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 14
3.4 miles to Islamorada
Islamorada, 33036
Welcome to 'World Class' fishing, diving, lobstering and relaxation in Islamorada. Venetian Shores location has deep water canals with ocean or...

from 5,000 USD

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Condo with 2 bedroom(s), 1.5 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 333070
Escape from the world in this beautiful island paradise. Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking...

from 700 USD

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Townhome with 3 bedroom(s), 2 bathrooms(s), sleeps 7
7.8 miles to Islamorada
Islamorada, 330036
Located at mile marker 74.5 in Islamorada easy drive from 5 airports, A short walk takes you to a private beach with key card access, tiki huts,...

from 1,750 USD

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House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
7.8 miles to Islamorada
Islamorada, 33036
Lovely private fenced and gated property with a in ground pool. Family and friends as well as avid fishermen will love this home. Downstairs has a...

from 7,000 USD

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Condo with 3 bedroom(s), 2.5 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
From your spacious Terrace with your cup of coffee or tea watch the sun come up over the Atlantic Ocean. Be ready to enjoy yourself in Islamorada....

from 2,500 USD

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House with 3 bedroom(s), 2.5 bathrooms(s), sleeps 8
5.8 miles to Islamorada
Islamorada, 33036
Enough really can't be said about this delightful beach front home, right in Islamorada. Ocean Terrace is located oceanfront (Atlantic Ocean) in...

from 3,950 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 8
6.2 miles to Islamorada
Islamorada, 33070
Once you enter into the fenced yard, you have arrived in paradise!! Welcome to this private oceanfront estate. Upstairs, there are 2 bedrooms and...
House with 5 bedroom(s), 3 bathrooms(s), sleeps 10
islamorada, 33036
This home is a renter's dream. It is located in the Village of Islamorada on the bay side. Almost immediate ocean access channel 2 or channel 5...

from 4,200 USD

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House with 1 bedroom(s), 1 bathrooms(s), sleeps 4
7.8 miles to Islamorada
Islamorada, 33036
Our home is located in an exclusive waterfront residential community with a private beach just for owners and guests. The beach has crystal clear...

from 99 USD

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House with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
3 miles to Islamorada
Islamorada, 33036
In the stunning village of islands, Islamorada in the Florida Keys, we have an immaculate newly refurbished ocean front 2 bed (large master &...

from 1,750 USD

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Condo with 1 bedroom(s), 1 bathrooms(s), sleeps 4
5.8 miles to Islamorada
Islamorada, 33070
Enjoy spectacular sunsets and the blue-green waters of the Florida Keys! Come to relax or come to play! Take advantage of great snorkeling and...

from 2,250 USD

Monthly


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Condo with 3 bedroom(s), 2.5 bathrooms(s), sleeps 6
7.8 miles to Islamorada
Islamorada, 33036
Accommodations: Condominium - 3 Bedrooms + Other (See Description) - 2.5 Baths - (Sleeps 6-8) COME TO PARADISE! Newest condominium complex in...

from 1,900 USD

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House with 3 bedroom(s), 2 bathrooms(s), sleeps 8
8.3 miles to Islamorada
Islamorada, 33036
Located on the prestige White Marlin Beach, considered one of the nicest natural sand beaches in the Florida Keys with great swimming + snorkling...
Apartment with 1 bedroom(s), 1 bathrooms(s), sleeps 2
8.3 miles to Islamorada
islamorada, 33036
The Jetson's House - Located on the prestige White Marlin Beach. Considered one of the nicest natural sand beaches in the Florida Keys with great...

from 3,000 USD

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Townhome with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33036
Imagine yourself living the island dream in a fully renovated 5 star ocean side home along 'Millionaires Row' in Islamorada. The owners of this...

from 1,250 USD

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House with 5 bedroom(s), 4 bathrooms(s), sleeps 9
6.2 miles to Islamorada
Islamorada, 33070
Beautiful private pool home directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 4 bedroom, 3 bath...

from 4,500 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 8
0.3 miles to Islamorada
Islamorada, 33036
San Roc Estate is an intimate, cozy and secluded ocean front home with breathtaking open water views of the Atlantic Ocean. This unique 4/3 home...

from 5,750 USD

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Townhome with 2 bedroom(s), .5 bathrooms(s), sleeps 6
6.3 miles to Islamorada
Islamorada, 33036
Enjoy our PRIVATE BEACH with panoramic views of the Gulf of Mexico ,spectacular sunsets! Excellent Fishing, snorkeling and boating in your...
House with 3 bedroom(s), 3 bathrooms(s), sleeps 6
0.2 miles to Islamorada
Islamorada, Florida, 33036
Come and enjoy our beautiful Key West style duplex located on a one-of-a-kind, very secluded street in Islamorada, Florida. The home is ...

from 142 USD

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Vacation rental with 3 bedroom(s), 2 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Enjoy a beautiful solar heated pool with Jacuzzi on the premises. Private homeowner's sandy beach access to swim and enjoy sunsets!! Come to...

from 250 USD


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Studio with 0 bedroom(s), 1 bathrooms(s), sleeps 2
7.3 miles to Islamorada
Islamorada, 33036
Book August 18 - 25 and SAVE $300 off the $1100 rate and stay for $800, everything included! All our rates are everything included...no hidden or...

from 800 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 6
0.7 miles to Islamorada
Islamorada, 33036
Casa Venetia has 3 bedrooms & 3 bathrooms. It accommodates 6 people, and sits in the lovely and quiet residential neighborhood of Plantation Key....

from 6,000 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
Castello Buona Vita is a luxury Islamorada vacation rental located bayside in Islamorada on Lower Matecumbe Key in the famed Florida Keys. The...

from 6,000 USD

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House with 4 bedroom(s), 3.5 bathrooms(s), sleeps 12
7.8 miles to Islamorada
Islamorada, 33036
This lovely Islamorada canal home has 4 bedrooms and 3.5 baths Sleeps 8 the house is 4 years old. Gorgeous Tile throughout. Includes a fabulous...

from 6,600 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 6
1.7 miles to Islamorada
Islamorada, 33026
Beautiful 3 bedroom 3 full bath luxury rental in the heart of Islamorada. Walking distance to many restaurants and town. Located ocean side, in a...

from 1,995 USD

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Townhome with 2 bedroom(s), 1.5 bathrooms(s), sleeps 5
1.2 miles to Islamorada
Islamorada, 33036
Enjoy spectacular water views from your brand new luxury townhome, complete with private balcony, gourmet kitchen and fully appointed living...

from 1,275 USD

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House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
1.2 miles to Islamorada
Islamorada, 33036
MONTHLY RENTALS ONLY. 'LaHonda' is a charming Key West style three-bedroom, two-bath home located in the heart of Islamorada in the Florida Keys....

from 6,000 USD

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House with 4 bedroom(s), 4 bathrooms(s), sleeps 10
8.7 miles to Islamorada
Islamorada, 33036
WOW! Unlimited bayfront views from the house and the heated pool. Imagine sitting in the pool with your favorite beverage and watching the sunset....

from 12,000 USD

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Cottage with 2 bedroom(s), 2 bathrooms(s), sleeps 8
0.4 miles to Islamorada
Islamorada, 33036
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Kottage...

from 895 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33036
Village of Islamorada License Number VR-113. *Be sure to email the owner from this web page to get quick information on rates and...

from 1,600 USD

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Studio with 0 bedroom(s), 1 bathrooms(s), sleeps 4
5.3 miles to Islamorada
Islamorada, 33070
Come relax in paradise in the heart of the Florida of Keys. Relax by the heated pool overlooking the turquoise bay; fish from the dock, snorkel in...

from 450 USD

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Condo with 3 bedroom(s), 2.5 bathrooms(s), sleeps 6
7.8 miles to Islamorada
Islamorada, 33036
Escape the everyday stress of the mainland for the quiet, relaxed atmosphere of the Florida Keys in an exclusive gated community. This is a...

from 2,000 USD

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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 6
5.3 miles to Islamorada
Islamorada, 33036
Ocean Harbor is one of the most exclusive condominiums in Islamorada. Enjoy spectacular ocean views in this second floor condo that also overlooks...

from 5,000 USD

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Hotel with 1 bedroom(s), 1 bathrooms(s), sleeps 4
Islamorada, 33036
Resort complex which includes a great restaurant and bar, dockside lounge and waterview. Full service marina and watersports. Located in...
House with 4 bedroom(s), 4.5 bathrooms(s), sleeps 6
3.4 miles to Islamorada
Islamorada, 33036
Luxury Venetian Shores Canal Home With Heated Pool, Elevator.

from 3,500 USD

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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33070
Islamorada License #-VR-09-52 Wheel chair accessible with Roll in Shower. Gated luxury property -on the water, Bayside, at Futura Yacht Club...

from 800 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 8
9.5 miles to Islamorada
Islamorada, 33037
Immediate ocean access with beautiful views upstairs & down. Upstairs the kitchen, dining, and living rooms all provide ocean views. There are 3...
Townhome with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33036
Experience total seclusion in a ten-unit, luxury, oceanfront complex called Port of Call, nestled along millionaire's row on Plantation Key,...

from 1,200 USD

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Villa with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
1.2 miles to Islamorada
Islamorada, 33036
This is a 2 bedroom 2 bath house with a full kitchen, living room, dining room and washer and dryer. The master bathroom has a large soaking tub...

from 7,700 USD

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House with 3 bedroom(s), 2 bathrooms(s), sleeps 7
7.8 miles to Islamorada
Islamorada, 33036
Stilt home with lushly landscaped grounds. Comfortable and easy to use. Full set of amenities, all the comforts of home. Dockage for up to 60 foot...

from 3,500 USD

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Villa with 2 bedroom(s), 1 bathrooms(s), sleeps 4
0.4 miles to Islamorada
Islamorada, 33036
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area...

from 1,095 USD

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House with 4 bedroom(s), 4 bathrooms(s), sleeps 7
7.8 miles to Islamorada
Islamorada, 33036
The Morada Sands is luxurious residence located in the fishing capital of the world, Islamorada. Shopping and dining are just minutes away. You...

from 6,600 USD

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House with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
3 miles to Islamorada
Islamorada, 33036
This new oceanfront resort home with two bedrooms and two and a half bathrooms will accommodate six guests (four adults). Anglers Reef is a gated...

from 1,595 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 8
3.9 miles to Islamorada
Islamorada, 33036
NEW huge swimming pool & deck just completed! This is an incredible home featuring nothing but the best in high-end Florida Keys style décor and...
House with 3 bedroom(s), 3 bathrooms(s), sleeps 7
3.4 miles to Islamorada
Islamorada, 33036
Huge 40 foot swimming pool recently added. This is an incredible home featuring nothing but the best in high-end Florida Keys style décor and...

from 5,950 USD

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Condo with 2 bedroom(s), 3 bathrooms(s), sleeps 11
4.4 miles to Islamorada
Islamorada, 33036
Get away from all the stress. Come and relax in our beautiful place in the Florida Keys. The Executive Bay club is located in Islamorada, the...
House with 3 bedroom(s), 2.5 bathrooms(s), sleeps 8
3 miles to Islamorada
Islamorada, 33036
A magnificent & truly OceanFRONT home at Mile Marker 85 in exclusive Angler's Reef - a boutique complex of 52 homes inspired by Native Conch &...

from 2,350 USD

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House with 5 bedroom(s), 4 bathrooms(s), sleeps 12
2.1 miles to Islamorada
islamorada, 33036
Property Includes: Located directly on 1 mile of white sandy beach on the Atlantic Ocean 3 Master Suites with sliding patio doors opening onto...

from 5,000 USD

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Estate with 7 bedroom(s), 5.5 bathrooms(s), sleeps 14
4.1 miles to Islamorada
Islamorada, 33036
The Florida Keys Largest, Most Prestigious Vacation Rental Home Available!! Come stay in your own luxurious Oceanfront Mansion...for less than...

from 6,000 USD

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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 4
0.7 miles to Islamorada
Islamorada, 33036
Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to lushly landscaped grounds. Only...

from 3,500 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 10
3 miles to Islamorada
Islamorada, 33036
Located Oceanfront at Mile Marker 85, this 4 bedrooms, 3 baths, sleeps 8-10 and is a favorite amongst guests!. Protected deep-water dockage for...

from 3,500 USD

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House with 7 bedroom(s), 6 bathrooms(s), sleeps 10
8.7 miles to Islamorada
Islamorada, 33036
This immaculate and spacious three (3) story bayside waterfront pool home is a perfect vacation rental for a family reunion, a group desiring lots...
House with 3 bedroom(s), 1.5 bathrooms(s), sleeps 6
0.4 miles to Islamorada
Islamorada, 33036
This is Paradise South!! Bay side traditional , but modernized, conch home facing west for spectacular sunsets and view. Secluded swimming area...

from 6,000 USD

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House with 5 bedroom(s), 3 bathrooms(s), sleeps 10
8.7 miles to Islamorada
Islamorada, 33036
Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and private setting. Ryan's place has 5...
House with 3 bedroom(s), 2 bathrooms(s), sleeps 8
0.3 miles to Islamorada
Islamorada, 33036
This 2 bedroom 2 full bath vacation home is located on the peaceful northern end of Islamorada, in the quiet residential neighborhood of Venetian...

from 2,300 USD

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Villa with 3 bedroom(s), 3.5 bathrooms(s), sleeps 6
1.2 miles to Islamorada
Islamorada, 33036
This is a 3 bedroom 3 bathroom house with a wonderful full kitchen, 2 living spaces, dining room, library, and washer and dryer. 2 Master suites,...

from 17,500 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 12
7.8 miles to Islamorada
Islamorada, 33036
Village of Islamorada Vacation Rental License #VR-112 Located on a beautiful crystal-clear bayside canal, this house provides a beautiful view...
House with 3 bedroom(s), 3 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33036
Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' If you are looking for gold sinks, with gold fixtures, this is not the...

from 1,500 USD

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House with 4 bedroom(s), 3 bathrooms(s), sleeps 8
8.7 miles to Islamorada
Islamorada, 33036
This House Sits Directly On The Water With Own Lagoon. Located in a private neighborhood on Lower Matecumbe (MM74.5) this is the perfect place to...

from 4,500 USD

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House with 5 bedroom(s), 3 bathrooms(s), sleeps 13
0.3 miles to Islamorada
Islamorada, 33036
Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and...

from 6,200 USD

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Condo with 3 bedroom(s), 2.5 bathrooms(s), sleeps 6
7.8 miles to Islamorada
Islamorada, 33036
Gorgeous new Bay Harbour gated condo community on Lower Matecumbe, MM 74 1/2.Lush tropical landscaping, heated pool with jetted spa, two lighted...

from 2,100 USD

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House with 4 bedroom(s), 4.5 bathrooms(s), sleeps 8
0.3 miles to Islamorada
Islamorada, 33036
Gorgeous home in the premier gated community in Islamorada. Bonefish Bay, an enclave of 12 Key West-style homes with all the amenities of a large...

from 5,000 USD

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Apartment with 0 bedroom(s), 1 bathrooms(s), sleeps 4
1.2 miles to Islamorada
Islamorada, 33037
There is simply no other way to enjoy a Florida Keys Vacation at a lower price. Everything in this cute One Bedroom Apartment is BRAND NEW...
House with 4 bedroom(s), 3 bathrooms(s), sleeps 10
3.9 miles to Islamorada
Islamorada, 33036
This beautiful canal front home with brand new heated swimming pool is centrally located in the heart of Islamorada. Just 1/2 mile from world...
House with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
3 miles to Islamorada
Islamorada, 33036
The Reel Retreat at Angler's Reef offers the best that the Florida Keys has to offer: diving, snorkeling, kite boarding and of course, great...

from 1,350 USD

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House with 4 bedroom(s), 4.5 bathrooms(s), sleeps 8
6.3 miles to Islamorada
Islamorada, 33036
Bonefish Bay is a private gated community of only 12 homes sitting on 350 feet of shoreline and 5 acres. The Snook House sits just 50 feet to the...

from 5,500 USD

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House with 4 bedroom(s), 4.5 bathrooms(s), sleeps 8
6.3 miles to Islamorada
Islamorada, 33036
Bonefish Bay is a private secluded community of 12 homes on 5 acres overlooking the Bay with 350 feet of shoreline. The Starfish house sits just...

from 6,000 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 7
4.4 miles to Islamorada
Islamorada, 33076
The home offers some very unique features and amenities. Probably the best feature is the location. Situated in a secluded forest setting next...

from 2,500 USD

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House with 3 bedroom(s), 2 bathrooms(s), sleeps 6
1.2 miles to Islamorada
Islamorada, 33036
Crooked Corners is a charming Key West Style three-bedroom, two-bath home located in the heart of Islamorada on the Florida Keys. Nestled in a...

from 6,000 USD

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Condo with 2 bedroom(s), 2 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33070
Privately owned condominium at the Futura Yacht Club in the Village of Islamorada with wireless Internet Access. Futura is located on the Gulf of...

from 700 USD

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House with 4 bedroom(s), 2.5 bathrooms(s), sleeps 8
1.2 miles to Islamorada
Islamorada, 33036
Ocean Terrace is located oceanfront (Atlantic Ocean) in Islamorada, at Mile Marker 81.5; this 3 bedroom home plus den sleeps 8-10. Gated with...

from 4,250 USD

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House with 4 bedroom(s), 3.5 bathrooms(s), sleeps 10
0.3 miles to Islamorada
Islamorada, 33186
Beautiful canal-front home located in prestigious Venetian Shores sub-division. 100 foot dock with davits and fish cleaning station on wide deep...
House with 3 bedroom(s), 2 bathrooms(s), sleeps 8
7.8 miles to Islamorada
Islamorada, 33036
122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of...
House with 2 bedroom(s), 2 bathrooms(s), sleeps 6
5.8 miles to Islamorada
Islamorada, 33036
This beautiful 2 Bedroom 2 Bathroom neat home is a waterfront retreat located on 103 Cortez Dr, Islamorada. This fantastic community is one of...

from 2,290 USD

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House with 1 bedroom(s), 1 bathrooms(s), sleeps 5
6.8 miles to Islamorada
Islamorada, 33036
1 bedroom, 1 bathroom house in the most desirable part of Florida Keys - the Village of Islamorada; king size bed in bedroom, livingroom has 1...

from 950 USD

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House with 2 bedroom(s), 2.5 bathrooms(s), sleeps 6
7.6 miles to Islamorada
Islamorada, 33036
This new oceanfront resort home with two bedrooms and two and a half bathrooms will accommodate six guests. Anglers Reef is a gated oceanfront...

from 1,400 USD

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House with 3 bedroom(s), 1 bathrooms(s), sleeps 6
4.4 miles to Islamorada
Islamorada, 33036
Fisherman’s Retreat Think stilt house in the 'Caribbean' on the water - a broad protected harbor with immediate ocean access and a 70 foot...

from 3,100 USD

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House with 3 bedroom(s), 3 bathrooms(s), sleeps 8
5.3 miles to Islamorada
Islamorada, 33036
Unique Cedar Home nestled on a Private Drive in Millionaires Row Islamorada - with PEACEFUL water views. Enjoy the privacy and 225' of waterfront...

from 2,100 USD

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Vacation rental with 2 bedroom(s), 2 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Escape to Islamorada and enjoy this beautifully updated 2 bedroom / 2 bath townhouse located in Executive Bay Club a bay front property. This is a...
Vacation rental with 2 bedroom(s), 2 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport...

from 320 USD


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Vacation rental with 5 bedroom(s), 3 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Very private, very large, home in Islamorada with heated pool and 120 foot of deep water dockage.

from 500 USD


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Vacation rental with 2 bedroom(s), 1 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
Vacation Mobile Home Rental at Sea Breeze RV and Mobile Home Park Islamorada, Florida Keys Mile Marker 87.5 Oceanside Totally renovated Air...

from 114 USD


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Vacation rental with 4 bedroom(s), 4 bathrooms(s)
0.2 miles to Islamorada
Islamorada, Florida, 33036
This beautiful 4 bedroom/ 4 bathroom home has a 70' dock. Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is...

from 429 USD


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Vacation rental with 2 bedroom(s), 2 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
This delightful, fully remodeled 2 bedroom/2 bath home is available year round. Corner Unit on the 6th floor has the best views. Screened in...

from 168 USD


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Vacation rental with 2 bedroom(s), 2 bathrooms(s)
13.4 miles to Islamorada
Islamorada, Florida, 33001
Set on an oceanfront resort with ocean views all around, this new Florida Keys cottage is a great vacation cottage to accommodate anyone looking...

from 209 USD


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Vacation rental with 6 bedroom(s), 6 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
The Falcon Estate is a beautiful three story home located in the famous Florida Keys. This luxurious home features ocean views from most rooms, a...

from 1,000 USD


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Vacation rental with 3 bedroom(s), 3 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or...
Vacation rental with 2 bedroom(s), 2 bathrooms(s)
7.7 miles to Islamorada
Islamorada, Florida, 33070
Located at Mile Marker 90 in the Florida Keys our 2 Bedroom/2 Bath Condo offers unobstructed views of the Atlantic Ocean. The complex offers a...

from 157 USD


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