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.

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Vacation Rentals in Islamorada

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kEYS WITH EASE 3/3 Ocean Canal - WEEKS OPEN IN FEBRUARY!-CALL NOW – Property 242664

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, pets considered
  • $1,000 - $1,600/week
  • Calendar Last Updated On: Nov 21, 2009
Village of Islamorada License Number VR-09-62. A brand new kitchen with all wood cabinets, granite counter tops and GE profile stainless appliances greets you...

SPECTACULAR Open Water Views & Private Dockage-Is on both the bay and beach – Property 223571

  • Islamorada rental - house, 3 bedrooms, sleeps 10, 2 bathrooms, near the ocean, waterfront, balcony
  • Calendar Last Updated On: Nov 21, 2009
Spectacular long water views from inside and out of this secluded estate property! The only thing more beautiful than the view is the large dock.

Bayfront Paradise Heated Pool Home on the Bay in Islamorada – Property 243094

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, pool
  • $1,800 - $2,200/week
  • Calendar Last Updated On: Nov 20, 2009
-Large Bayfront Home with Heated Pool - Islamorada is the 'Fishing Capital of the World'...Fishing Guides available. -Very private and secluded also fenced -Single...

Tarpon Cove: Best Islamorada Vacation Rental – Property 153876

  • Islamorada rental - house, 3 bedrooms, sleeps 6, beach, waterfront, air-conditioning
  • $1,700 - $1,900/week
  • Calendar Last Updated On: Nov 20, 2009
Pristine Islamorada canal front home with 70' of concrete dock and fish cleaning station. Located on Mile Marker 73.5 bayside in the peaceful Tollgate Shores...

OceanFRONT home new 2008, panoramic ocean views, pool, beach, WIFI - see Reviews – Property 186650

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, waterfront, pool
  • $1,990 - $3,050/week
  • Calendar Last Updated On: Nov 21, 2009
A magnificent oceanfront home (TRULY OceanFRONT!) at Mile Marker 85 in exclusive Angler's Reef - 51 homes inspired by Native Conch & British West Indies...

Luxury home overlooking pool with open water view of Atlantic Ocean – Property 267141

  • Islamorada rental - house, 2 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, waterfront, pool
  • $2,650 - $3,250/week
  • Calendar Last Updated On: Nov 20, 2009
Welcome to our lovely home in Islamorada here in the Florida Keys. Often promoted as the Sport-fishing Capitol of the World, you can fish, swim, kite or windsurf,...

Luxury Waterfront Villa with Pool, Jacuzzi and 70 ft Dock – Property 138443

  • Islamorada rental - villa, 4 bedrooms, sleeps 10, 4 bathrooms, near the ocean, waterfront, pool
  • Calendar Last Updated On: Nov 19, 2009
Plan your Keys Getaway to this absolutely beautiful, spacious waterfront home with swimming pool, Jacuzzi and dock. Enjoy unforgettable sunsets while relaxing...

Private heated pool vacation Home ,deep canal ,70ft dock VenetianShores Flo Keys – Property 204162

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, pool
  • Calendar Last Updated On: Nov 19, 2009
This two or 3 bedroom, two bath or 3 full bath vacation home is located on the peaceful northern end of Islamorada, in the quiet residential neighborhood of...

Charming cottage style home on quiet street – Property 254609

  • Islamorada rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, 1 half bath, beach, waterfront, pool
  • $1,450 - $1,700/week
  • Calendar Last Updated On: Nov 18, 2009
Welcome to our lovely home in Islamorada here in the Florida Keys. Often promoted as the Sport-fishing Capitol of the World, you can fish, swim, kite or windsurf,...

Venetian Shores .. Pool Home Quick Ocean/Bay Access – Property 177340

  • Islamorada rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, near the ocean, waterfront, pool
  • Calendar Last Updated On: Nov 18, 2009
Beautiful canal-front home located in prestigious Venetian Shores sub-division. 100 foot dock with davits and fish cleaning station on wide deep water canal.
SPECIAL OFFER! Discount $50.00 Off Weekly Rate November 19 - December 19

Tropically Furnished Condo with Ocean Views – Property 301565

  • Islamorada rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, tennis court
  • $750 - $1,000/week
  • Calendar Last Updated On: Nov 19, 2009
Privately owned condominium at the Futura Yacht Club in the Village of Islamorada with wireless Internet Access. Futura is located on the Gulf of Mexico and is a...

'Islamorada Sol' Beautiful Home with Dock & Beach – Property 231610

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, near the ocean, terrace
  • Calendar Last Updated On: Nov 17, 2009
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 deep water canal...

Mermaid Cottage – Property 7012797

  • Islamorada rental - house, 3 bedrooms, sleeps 6, 2 bathrooms,
  • Calendar Last Updated On: Nov 17, 2009
Minimum Rental 28 Days. Absolutely enchanting! Words are hard to find to accurately describe the charm and tropical personality found in this home.

Islamorada Oceanfront Vacation Rental Home – Property 151270

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, balcony
  • Calendar Last Updated On: Nov 17, 2009
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 is situated on 2.5...

Beautiful Bayfront Condo with Marina, Pool and Beach (Futura Yacht Club) – Property 160322

  • Islamorada rental - condo, 3 bedrooms, sleeps 7, 2 bathrooms, beach, waterfront, tennis court
  • $700 - $950/week
  • Calendar Last Updated On: Nov 16, 2009
Quiet gated community at mile marker 88.5 bayside in Islamorada with world class fishing and diving,2 lighted tennis courts, large heated pool, large 65 slip marina,...

Tropical Paradise in the Village of Islamorada-Guest of Cheeca Lodge and Spa – Property 220594

  • Islamorada rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, near the ocean, village, pool
  • Calendar Last Updated On: Nov 16, 2009
Crooked Corners is a charming Key West Style three-bedroom, two-bath home located in the heart of Islamorada on the Florida Keys.

Oceanfront 5th Floor End Unit! Pool, Internet, Tennis, Panoramic Ocean Views – Property 151910

  • Islamorada rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, waterfront, sauna
  • $850 - $1,600/week
  • Calendar Last Updated On: Nov 20, 2009
Incredible Panoramic Ocean Views from this comfy and well cared for 5th floor fully-equipped end unit directly on the ocean, just steps from the water, in highly...

Brand New Canal Front Home with Ocean Views & Pool – Property 240743

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, near the ocean, waterfront, pool
  • Calendar Last Updated On: Nov 16, 2009
Immediate ocean access with beautiful views upstairs & down. Upstairs the kitchen, dining, and living rooms all provide ocean views.

Beautiful Luxury Townhouse at Executive Bay Club Florida Keys – Property 204997

  • Islamorada rental - townhome, 2 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, pool
  • $1,400 - $1,500/week
  • Calendar Last Updated On: Nov 19, 2009
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 the Wonderful...

Quiet Oceanfront Condo with Superb Oceanview – Property 217210

  • Islamorada rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, waterfront, tennis court
  • $700 - $900/week
  • Calendar Last Updated On: Nov 14, 2009
This 750 square foot one-bedroom/one-bath, oceanfront condo features a balcony overlooking the Atlantic Ocean. We have a small beach area on the water for sunbathing...
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