Visit the Village: Islamorada

It sounds just as exotic as the best Caribbean islands out there, but it’s only a few miles off the coast of everyday, regular Florida. Thanks to natural conditions that include reefs, The Everglades and waters filled with an assortment of fish, Islamorada is a wild kind of place that will certainly have you reeling in more than you can handle.


Honeymooners, families and adventurers can all find what they’re looking for here in this colorful Florida Key. Islamorada means Village of Islands, so you’ll constantly feel that you’ve escaped the mainland and needn’t worry about what’s going on in the real world.


Here in the Sport Fishing Capital, one of your first orders of business will be to charter a boat and head out for a deep-sea expedition. If catching your own dinner doesn’t appeal to you, take a kayak tour, hike for fun and fitness, do some shopping or visit the Theater of the Sea Aquarium.


There’s also tennis, snorkeling, hanging out at happy hour, and cooking it your own way on your vacation rental patio. And if time and energy permit, you can even head south and visit one of the other Florida Keys. State parks, sunsets to die for and plenty of condos and beach houses to claim as your own further add to the allure of this Upper Keys gem, however, so there’s no need to wander too far once you’ve settled in.


It’s no secret that island living is better, so give it a whirl without worrying about passports or lengthy flights. Islamorada is waiting, and this is your official welcome to the village.

Destination: Search

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Vacation Rentals in Islamorada

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Open Water Sunset View, WI FI, Huge Warm Pool, Optional Deeded Dock – Property 352115

  • Islamorada rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, accept credit card, Beach, Waterfront
  • $800/week
  • Calendar Last Updated On: May 23, 2013
Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and basketball and volleyball courts.

Angler's Reef Coastal Conch Style Vacation Home in Islamorada, Fl. – Property 944148

  • Islamorada rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, accept credit card, Beach, Near The Ocean, Resort, Village, Waterfront
  • Calendar Last Updated On: May 23, 2013
This Coastal Conch Style Cottage has recently been updated to accommodate vacation renters and their families. This Cottage has all new furnishings and accessories...

LITTLE BAY - Lower Duplex – Property 3249105

  • Islamorada rental - villa, 2 bedrooms, sleeps 6, 2 bathrooms, Beach, Air Conditioning
  • $2,400/week
  • Calendar Last Updated On: May 23, 2013
Minimum Rental: 3 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical...

LITTLE BAY - Upper Duplex – Property 3249104

  • Islamorada rental - villa, 2 bedrooms, sleeps 6, 2 bathrooms, Beach, Balcony
  • $2,400/week
  • Calendar Last Updated On: May 23, 2013
Minimum Rental: 3 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting...

Fabulous View, Split 2/2 Up, 2/1 Down, Ideal for 2 Families – Property 158012

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, Near The Ocean, Waterfront, Lawn / Garden
  • $2,200 - $2,600/week
  • Calendar Last Updated On: May 23, 2013
Islamorada is the fishing capital of the world! Renowned for Tarpon, Sailfish, Bone Fish, Canoeing, Wind Surfing, Lobster and reef fish, Dolphin (both edible and...

SUNSHINE PLACE – Property 3249117

  • Islamorada rental - villa, 1 bedroom, sleeps 2, 1 bathroom, Beach, Air Conditioning
  • $950 - $1,125/week
  • Calendar Last Updated On: May 22, 2013
Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a...

Anglers Reef Truly OceanFRONT 3BR 2.5 bath home Lg Decks/Pool/WIFI/4 Flatscr TVs – Property 186650

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, Beach, Downtown, Resort, Village, Waterfront, Communal Pool
  • $2,400 - $3,200/week
  • Calendar Last Updated On: May 22, 2013
THE VIEWS DON'T GET ANY BETTER THAN THIS! We are the ONLY truly OceanFRONT home for rent - and the only 3 bedroom home- in exclusive ANGLER'S REEF, a boutique...

Oceanfront Anglers Reef, Islamorada, Florida Keys, Video Tour – Property 224013

  • Islamorada rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, accept credit card, Beach, Resort
  • $1,395 - $1,595/week
  • Calendar Last Updated On: May 23, 2013
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 oceanfront property...

Paradise just steps away! – Property 399735

  • Islamorada rental - condo, 1 bedroom, sleeps 4, 1 bathroom, accept credit card, Near The Ocean, Waterfront
  • Calendar Last Updated On: May 23, 2013
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 diving along with...

Immaculate Fully Furnished 2/2 With Breathtaking Ocean Views – Property 167594

  • Islamorada rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, Beach, Resort, Waterfront, Communal Pool
  • $775 - $1,225/week
  • Calendar Last Updated On: May 20, 2013
Immaculate 2 bedroom, 2 bathroom condo with breathtaking views of the Atlantic Ocean from the living room balcony. This condo boasts a KING bed in master bedroom, 2...

Beautiful Captain's Cove – Property 218650

  • Islamorada rental - villa, 3 bedrooms, sleeps 8, 2 bathrooms, Beach, Waterfront, Balcony
  • $1,450 - $1,650/week, per person
  • Calendar Last Updated On: May 20, 2013
Relax and enjoy a peaceful get-away in beautiful Islamorada. This unique, upscale, three-bedroom/two-bath home is nestled on a bay overlooking the ocean.

Angler's Reef, Beautiful new home, Ocean front. Islamorada FL – Property 220629

  • Islamorada rental - townhome, 2 bedrooms, sleeps 4, 2 bathrooms, 1 half bath, Beach, Near The Ocean, Waterfront, Communal Pool
  • $1,200 - $1,400/week
  • Calendar Last Updated On: May 20, 2013
This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 51 homes . Quaint streets & walking paths wind through this village-styled...

Captivating Tropical Villa: 3BR w/ Dock, Hot Tub & Rooftop Patio – Property 3012158

  • Islamorada rental - house, 3 bedrooms, sleeps 6, 4 bathrooms, Beach, Near The Ocean
  • $2,500/week
  • Calendar Last Updated On: May 20, 2013
Weekly Rentals Only Designers home located in Venetian Shores, MM86. 70ft dock space on a clean, deep water canal that leads to Snake creek where there is access to...

Paradise Point - Canal Front Home with Boat Slip - Pool and Jacuzzi! – Property 3012135

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, Near The Ocean, Waterfront, Jacuzzi
  • Calendar Last Updated On: May 20, 2013
This beautiful canal front home with a brand new heated swimming pool is centrally located in the heart of Islamorada. Just 1/2 mile from world famous Holiday Isles...

Millionaire’s Playground: Custom Gated Home with Ocean Views, Pool & Wet Bar – Property 3012161

  • Islamorada rental - house, 7 bedrooms, sleeps 16, 6 bathrooms, Private Pool, Tennis Court
  • Calendar Last Updated On: May 20, 2013
Peeking through the security gate of this 6.5 acre paradise, you can’t help feeling that you are entering an enchanted hideaway full of hidden treasures.

Gulf View Drive – Property 3012176

  • Islamorada rental - house, 3 bedrooms, sleeps 14, 2 bathrooms, Beach, Near The Ocean, Jacuzzi
  • Calendar Last Updated On: May 20, 2013
Located on the prestige White Marlin Beach, considered one of the nicest natural sand beaches in the Florida Keys with great swimming + snorkeling right off the...

Islamorada Oceanfront Beauty: Private Heated Pool & Your Own 300 Foot Pier! – Property 3013630

  • Islamorada rental - house, 5 bedrooms, sleeps 9, 4 bathrooms, Waterfront, Air Conditioning
  • Calendar Last Updated On: May 20, 2013
Islamorada Oceanfront Beauty is a special home with amenities galore, including a beautiful private heated swimming pool home directly on the ocean.

'Island Paradise' Best Fishing Area – Property 169166

  • Islamorada rental - townhome, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, accept credit card, Near The Ocean, Waterfront
  • Calendar Last Updated On: May 21, 2013
This very clean and nicely decorated, newly renovated townhouse is located on the bay side in the heart of Islamorada on mile marker 76.

Islamorada Beachfront Beauty - Just Another Day in Paradise! – Property 3012144

  • Islamorada rental - house, 4 bedrooms, sleeps 12, 4 bathrooms, wheelchair accessible, Beach
  • Calendar Last Updated On: May 20, 2013
Just another day in paradise! This beautiful oceanfront home has a pool and a private beach. Each day you can view a magnificent sunrise and sunset over the ocean.

Tropical Beauty: Venetian Shores Canal Front Home! Private Pool & 70' Dock! – Property 3013474

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, Near The Ocean, Waterfront, Private Pool
  • Calendar Last Updated On: May 20, 2013
This beautiful canal front home is in Venetian Shores, one of the most sought-after neighborhoods in the Florida Keys. Park your boat at the 70' dock and spend your...
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