Vacation Rentals

Welcome to Islamorada Florida Vacation Rentals

Islamorada Travel and Vacation Rental Overview

Islamorada in the Florida Keys is a short drive down the island chain from Miami and mainland Florida. The islands boast the largest Florida Keys fishing fleet and one would guess that being dubbed the "Sportfishing Capital of the World" makes that possible.

Islamorada means "purple isles" and from a look around at the resorts and shops you can indeed see what they are talking about. Islamorada has a focus on fishing but there are plenty of other things to do and see in the area too.

Islamorada, a "Village of Islands," is an incorporated village in Monroe County, Florida, on the islands of Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key in the Florida Keys.

The village was incorporated on November 4, 1997. Prior to this date, Islamorada was only considered to be on the island of Upper Matecumbe Key.

As of the 2000 census, the village had a total population of 6,846. As of 2007, the population recorded by the U.S. Census Bureau is 6,386.

The name Islamorada, meaning "purple island", came from early Spanish explorers in the area. Its pronunciation has been Anglicized to aisle-a-more-AH-dah. Islamorada was hit almost directly by the Labor Day Hurricane of 1935, causing 423 deaths. A memorial, including the ashes of over 300 victims, exists today at Overseas Highway mile marker 82.

Islamorada, Florida is a training base for several members of The Race Club.

"Island Home" was the name of the schooner built in 1885 on Plantation Key by "Johnny Brush" Pinder, to carry passengers and cargo between these Islands and to the mainland. Its name in Spanish, "Islamorada", was later adopted as the name for the communities on these islands. The four spans of the Channel Two Bridge, built in 1907, represent the later connection of these four islands to the mainland via the Flagler Railroad, which was completed in 1912.

Alligator Reef Lighthouse was built in 1873, on the site of the wreck of the USS Alligator, which ran aground while on duty in 1821, protecting these islands from pirates. Today the lighthouse serves as both a beacon of safety and of welcome for mariners in our waters, and can be seen from the shores of all four islands.

All three images of the Village seal - the "Island Home", the Channel Two Bridge and the lighhouse at Alligator Reef - represent the work of human hands. Their place in the seal honors the enormous challenges bravely and joyfully faced by those who went before us in creating communities on these islands.

The four islands themselves are individual in size, shape and character, but the people on them share the same spirit of pioneer confidence that drew the first settlers to these shores. A protective chain of offshore reefs provides the quiet waters and gentle waves that surround the islands. The abundant marine life of those reefs and the shallow waters surrounding these islands is represented by the flashing brilliance of a leaping tarpon.

Lignum Vitae blossoms in the seal represent the precious uniqueness and vitality of our native hardwood hammocks and tropical plant life. The coconut palm represents the warm welcome offered to those who, like the coconut palm itself, have come from other places to make this their new island home.

Islamorada, long recognized as the "Sport Fishing Capital of the World," is now an icon among sport divers for much the same reason, a massive population of tropical marine life. High profile coral heads and broad ledges shelter huge congregates of French grunt and goatfish, while regal queen angelfish casually graze amid the reef recesses. Friendly green moray eels swim freely along the spur-and-groove channels, and reclusive nurse sharks lurk beneath the overhangs. Islamorada offers a wide variety of shallow coral reefs, mini walls, shipwrecks, and even an underwater habitat for scientific research, the Aquarius. To learn more about Islamorada or any other manner of local lore,

 
 
       
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Islamorada Vacation Rental Homes

Houses 
Condo
Villa
Apartment
Cottages
 
Featured Florida Vacation Rentals 4all in Islamorada Property
Private pool vacation home located on deep canal
Bed: 3 Bath: 3 Sleep: 6, Type: House
Islamorada, Florida, United States
Islamorada, Florida Keys at MM86 in Venetian Shores. 2 or 3 bedroom/3BA private vacation rental pool home for rent by private owner on deep canal with immediate access to ocean/bay off of Snake Creek ... View Details
Port of Call
Bed: 2 Bath: 2.5 Sleep: 6, Type: Duplex
Islamorada, Florida, United States
Total seclusion in 10 unit oceanfront complex along millionaires row on Plantation Key, Islamorada, the Sport Fishing Capital of the World. Off the old highway, away from all the noise and traffic, ye ... View Details
Dolphin Point
Bed: 5 Bath: 5 Sleep: 14, Type: House
Islamorada, Florida, United States
Tropical Oceanfront Walled Estate..Protected Boat Basin ,Deep Water, Great Views, Keys Living at it\'s Best. This Property is located in the heart of Millionaires Row on Plantation Key, Islamo ... View Details
Islamorada Studio Condo
Bed: 1 Bath: 1 Sleep: 4, Type: Condo
Islamorada, Florida, United States
Our studio: Sleeps family of four maximum. Has fully furnished kitchen w/fridge , dishwasher , disposal , stove and microwave. Cable TV and phone , laundry on every floor , 2 elevators , air condition ... View Details
Miller House in Venetian Shores
Bed: 3 Bath: 3.5 Sleep: 6, Type: House
Islamorada, Florida, United States
This unusal Designers home is located in the Florida Keys, Islamarada,Fl. MM 86. The house invites you to enjoy outdoor activities such as boating, swimming,deep sea fishing or back water fishing. The ... View Details
Island Times
Bed: 3 Bath: 2 Sleep: 8, Type: House
Islamorada, Florida, United States
Come Play! Your 70-foot dock provides instant access to fun – whether boating, fishing, swimming or relaxing under the shady, palm-roof “Chickee.” Enjoy your privacy with independent upstairs/downstai ... View Details
Ocean Front, Beach, Jacuzzi... Islamorada Beach House
Bed: 2 Bath: 2 Sleep: 8, Type: House
Islamorada, Florida, United States
Islamorada Beach House is a Beautiful Gated 2 bedroom 2 bath, ocean front, private home with a sandy beach and Jacuzzi. Located in at Mile Marker 75, it has quickly become the favorite honeymoon home. ... View Details
Executive Bay Club Island Paradise S-10
Bed: 3 Bath: 2 Sleep: 8, Type: Townhouse
Islamorada, Florida, United States
Location: Islamorada, Islamorada Area, Keys, Florida, USA (Drive to Miami 1 hour, Key West 1.5 hour, Marathon 30 minute). Relax at Executive Bay Club in the Fabulous Florida Keys.!Executive Bay Club l ... View Details
Venetian Tropics
Bed: 2 Bath: 2 Sleep: 6, Type: House
Islamorada, Florida, United States
Located on the peaceful,northern end of Islamorada,in the quite residential neighborhood of Venetian Shores.This 2 bedroom 2 bathroom is wquipped with many extras including a heated 80 to 82 degrees s ... View Details
Executive Bay Club
Bed: 2 Bath: 2 Sleep: 6, Type: Condo
Islamorada, Florida, United States
Beautiful Bayside Townhouse. Located on Mile Marker 87.2 in the heart of Islamorada, \"Fishing capital of the World.\" Two bedroom and 2 baths, spacious, fully furnished. Sleeps 2-8. ... View Details
ISLAMORADA - FUTURA YACHT CLUB ON THE BAY WITH MARINA
Bed: 2 Bath: 2 Sleep: 6, Type: Condo
Islamorada, Florida, United States
Save $$$$$$ END OF SEASON SPECIALS !!! Call or email for availability Futura Yacht Club - Islamorada on the Bay. This two bedroom, two bath condominiums sleeps six comfortably. Fully-equipped Brand Ne ... View Details
Futura Yacht Club Penthouse with Marina & Boat Slip.
Bed: 2 Bath: 2 Sleep: 6, Type: House
Islamorada, Florida, United States
Save $$$$$$ END OF SEASON SPECIALS !!! Call or email for availability If you plan to Vacation in the next week or two - you may save Hundreds of Dollars due to last minute cancellations. e mail for Pr ... View Details
SuCasa Vacation Rentals
Bed: 8 Bath: 5 Sleep: 24, Type: House
Islamorada, Florida, United States
SuCasa is one acre of land with two private homes and a one bedroom apartment. There is a 116 foot dock that can handle a large boat. It also has a 40 foot lagoon style fresh water swimming pool and a ... View Details
Get Away Cedar Chalet
Bed: 2 Bath: 2 Sleep: 6, Type: House
Islamorada, Florida, United States
One of a kind Island Get Away w/Pool/Jacuzzi,Ocean Views. This 2 bedroom, 2 full baths on a secluded cul-de-sac across from the Atlantic Ocean with panoramic ocean views. This unique octagonal cedar h ... View Details
Oceanfront 2 BR/2BA Condo in Paradise
Bed: 2 Bath: 2 Sleep: 6, Type: Condo
Islamorada, Florida, United States
Just 90 minute drive from Miami Airport puts you in this Tropical Island Paradise. Choose from two units: one sixth-floor with panoramic ocean views, the other immaculate second floor with ocean views ... View Details
Dream Home in the Keys LEGAL WEELY RENTAL IN ISLAMORADA
Bed: 5 Bath: 3 Sleep: 11, Type: House
Islamorada, Florida, United States
Very Private 4000 square foot home on water. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and private setting. Five large bedrooms, four with ... View Details
Sandys Retreat
Bed: 4 Bath: 3 Sleep: 12, Type: House
Islamorada, Florida, United States
This is a beautiful, spacious home on a wide bayside canal, only minutes to the best fishing and diving in the Florida Keys. Watch the sunsets over Florida Bay from the large screened in porch! Sit ... View Details
Southern Diversion Estate
Bed: 5 Bath: 3.5 Sleep: 13, Type: House
Islamorada, Florida, United States
Southern Diversion is in the heart of beautiful Islamorada in the Florida Keys. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also f ... View Details
Seagulls Condominium
Bed: 1 Bath: 1 Sleep: 4, Type: Condo
Islamorada, Florida, United States
Oceanfront condo with beautiful view of the Atlantic Ocean and daily sunrises, Balcony with privacy, Small private beach area for sunbathing, fishing or barbeques, heated pool, kayak available for pad ... View Details
5th Floor End Unit at Mile Marker 90
Bed: 2 Bath: 2 Sleep: 4, Type: Condo
Islamorada, Florida, United States
Enjoy incredible value in this fully furnished vacation condo accommodation with a kitchen, living/dining area, and 2 bedrooms, 2 full baths directly on the crystal clear waters of the Atlantic Ocean ... View Details
Summer Sea 1 BR 1 BA Condo With Amazing Water Views
Bed: 1 Bath: 1 Sleep: 4, Type: Condo
Islamorada, Florida, United States
Tropically decorated direct bayview one bedroom one bathroom second floor condo in Islamorada (Plantation Key) the Sport fishing capitol of the world. Mile marker 88. Balcony with table and four chair ... View Details
 
 

Islamorada Attractions and Activities

History

Islamorada as a location name began in 1907 when William Krome platted a Upper Matecumbe Key subdivision titled "Townsite of Islamorada." Subsequent events perpetuated the name such as the naming of the railroad depot and establishment of the Islamorada Post Office in 1908. The use of the name slowly spread through usage even though in unincorporated Monroe County.

Islamorada incorporated on December 31, 1997 as "Islamorada, Village of Islands" is basically four separate and livable islands. Also included are two islands that are part of the Florida State Park system, Indian Key and Lignum Vitae Key and one private island, Tea Table Key. There are also small off-shore islands. Each island has its own unique history. So rather than repeat each island's history or loose some while condensing, each island has a link below. If you are not familiar with the locations, a basic location map is provided.

Why Vacation in Islamorada?

The perfect family destination, Islamorada and Islamorada vacation rentals entice visitors with its aqua blue waters, innumerable recreational activities and excellent lodging facilities. Be it diving, snorkeling, parasailing, wind surfing, kayaking, or boat racing, the four islands of Islamorada surrounded by the Atlantic Ocean and Florida Bay offer something to do in, under and above the water any time of the day. If you are a sports freak, you can look forward to wide range of fishing tournaments, races and other sporting challenges every month of the year.

Islamorada Vacation Rental Information

Situated between Key Largo and Marathon, vacation rentals in the tropical get-away of Islamorada include a wide choice of luxury condos, private cottages, beachfront homes, cabins, oceanfront villas and studios. Offering spectacular views of the towering coconut palms, and the white-sand beaches, and the overwhelming Atlantic Ocean and the Florida Bay, these Islamorada vacation rentals are the ultimate in design, style, and comfort. Ranging from 1 bedroom for a cozy twosome to 6 bedrooms to accommodate large groups, these Islamorada lodges offer every imaginable convenience and amenities including heated swimming pool, spa, beach, and lighted tennis courts, protected dockage, cable TV, stereo, CD player, fish cleaning station, and hammock in the shaded breezeway. On site and nearby activities include biking, fishing, wildlife viewing, golf, shopping, swimming, snorkeling and diving, water skiing, and boating.

Best Times to Visit Islamorada

The laid back attitude has made the Keys a great escape from the stress and busy lifestyles of the mainland any time of the year. The tropical weather and the beautiful waters that surround the islands of Islamorada are perfect for enjoying summer activities such as boating, fishing, snorkeling and diving. The peak season is between December to September and it is advisable that you book your Islamorada vacation rental well in advance. The crowds during this period are the maximum and this is the best time to enjoy the glorious scenery and indulge in activities such as wildlife viewing, fishing, boating, snorkeling, scuba diving at some of the planet's most important reef systems.

Attractions

  • THEATER OF THE SEA Marine Mammal Adventure Park. Eco tours, swim with Dolphins, Sea Lions, and Sting Rays, plus other programs in beautifully landscaped setting. Reservations required for swims. Come Share Our Adventure!
  • ISLAMORADA TENNIS CLUB Islamorada , FL 33036
  • LIGNUMVITAE KEY BOTANICAL STATE PARK Islamorada , FL 33036
  • WINDLEY KEY FOSSIL REEF GEOLOGICAL STATE PARK Islamorada , FL 33036
  • HISTORY OF DIVING MUSEUM Islamorada , FL 33036
  • ISLAMORADA QUEEN Islamorada , FL 33036
  • ISLAMORADA HISTORICAL BICYCLE TOUR Islamorada , FL
  • BAY AND REEF CO Islamorada , FL 33036 Customized trips for you and your guests! Discover the underwater world of the coral reef, eco-tours, fishing, swimming, picnicking and then leisurely tour into the shallow waters of the Florida Bay all in one adventure!
  • Islamorada: The Ecotourist's Playground

    If you think Montana is Big Sky Country, you should check out Islamorada. It is a gateway to one of the most varied watery wildernesses in America. Climb onto an ecotour boat here and you are in a stunning marine environment of coral formations, tropical fish and dolphin pods. Now head northwest into the fabled backcountry, and in just minutes you are in a world of manatees, crocodiles and roseate spoonbills. Some tour operators will take you all the way to Flamingo, a national park outpost situated where the Everglades spill into Florida Bay in Everglades National Park.

    If human-powered craft are more your style, you're in luck too. Vast sea-grass beds and shallow tidal flats are easily accessible from marinas, resorts, and parks along U.S. 1, the Overseas Highway. Kayaks and canoes are available for rent or you can hire a tour guide.

    Tiny Lignumvitae Key is a fascinating stop for paddlers or boaters who want to stroll through a tropical forest thriving atop the remains of an ancient coral reef. Today, the island is home to Lignumvitae State Park and Botanical Site.

    Lignum vitae is Latin for wood of life, and the lignum vitae tree was once used in ship building. The island bearing its name lies just a mile from U.S. 1 on the bay side, and is reachable only by boat, kayak or canoe. This raised patch of land, called a hammock, tops out at just 18-feet above sea level yet it is the highest point in the Keys. That might be why early 2Oth century settlers called it home. Today, you can still visit the Matheson House, built in 1919.

    Events & Festivals

  • NOVEMBER 14 TO NOVEMBER 16 IN ISLAMORADA Wine On The Water - A Wine Symposium
  • DECEMBER 04 IN ISLAMORADA Florida Keys Holiday Festival
  • FEBRUARY 20 TO FEBRUARY 21 IN ISLAMORADA Upper Keys Gigantic Nautical Flea Market
  • Latest Islamorada Vacation Rental News


    Castanet.net

    Map locates Islamorada, Fla., where Gene Hackman was injured while riding a ...
    Castanet.net
    The Florida Highway Patrol reports that Hackman was riding on an Islamorada street around 3 pm when the pickup hit the back of his bicycle, throwing him onto the grassy shoulder. No charges were immediately reported. Hackman won an Academy Award for ...
    Car strikes actor Gene Hackman, 81, in IslamoradaMiami Hurricanes (blog)
    Gene Hackman struck by car while riding bikeCNN
    81-year-old Oscar winner Gene Hackman injured while riding bike in Fla; has ...Washington Post

    all 551 news articles »


    USA. Marina Investment Group selected for sale of Caloosa Cove resort ...
    BYM News (press release)
    Situated on Lower Matecumbe Key in Islamorada, the resort's outstanding oceanfront footprint sits on approximately 10 acres and includes 30 condo units offered as timeshares, a full-service marina with dockage and dry storage units, residential real ...



    Bank of America closing Islamorada branch
    KeysNet
    By David Goodhue Bank of America is closing its Islamorada branch in March, company officials confirmed this week. The branch, at 8154 Old Highway, will shut its doors on March 30, said Christina Beyer Toth, Southeast media relations manager for Bank ...



    Father and Son Arrested for Extracting Corals and Marine Life in Islamorada
    NBC Miami
    The Florida Fish and Wildlife Conservation Commission received a call from the US Coast Guard in Islamorada saying that witnesses in the vessel Happy Cat were watching another small vessel at Alligator Reef Lighthouse remove corals from the reef, ...
    2 charged with poaching coralsLocal 10

    all 3 news articles »


    Hot Entries to Highlight Islamorada Chili Cook-Off Feb. 18-19
    Newman PR
    ISLAMORADA, Florida Keys – Amateur and professional cook-off contestants and wannabe world champions representing seven US states and Canada are busy testing their best recipes in preparation for the third annual Islamorada Chili Cook-Off. The ...


     

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