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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Keys with Ease 3/3 Ocean Canal - New Open Kitchen, Dock – 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 8, 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...

Secluded waterfront home with spectacular views!!! – Property 142418

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, garden
  • Calendar Last Updated On: Nov 8, 2009
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 enjoy all that the...

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 8, 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.

Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access – Property 201354

  • Islamorada rental - townhome, 2 bedrooms, sleeps 8, 2 bathrooms, beach, village, pool
  • $1,000 - $1,200/week
  • Calendar Last Updated On: Nov 7, 2009
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of Islamorada.

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 7, 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...

Beautiful Islamorada Boater's Paradise home in the Florida Keys – Property 192446

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, balcony
  • $2,100/week
  • Calendar Last Updated On: Nov 7, 2009
Boater's paradise is a beautiful canal front home with swimming pool, 4 bedroom/2 bathrooms, sleeps 8 in the famous Florida Keys.

$100-$400 Off Luxurious Waterfront Condo, 2 Master Bedrooms w/Private Baths – Property 321060

  • Islamorada rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, waterfront, jacuzzi
  • $1,500 - $2,000/week
  • Calendar Last Updated On: Nov 8, 2009
Best Location in Complex! Gorgeous Florida Keys condo rental is Licensed! Relax in this luxurious gated waterfront condominium.

NOV SAVINGS! OceanFRONT home, new 2008, panoramic ocean views, pool, beach, WIFI – Property 186650

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, waterfront, pool
  • $2,350 - $3,050/week
  • Calendar Last Updated On: Nov 7, 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...

Venetian Dream – Property 7008512

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 4 bathrooms, 1 half bath, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
Minimum Rental 28 Days. ***FALL BOOKING SPECIAL - Rent will be discounted by 10% on all reservations confirmed by 10-15-09*** Venetian Dream is a new single...

Beacon Reef #302 – Property 7009805

  • Islamorada rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, air-conditioning, balcony
  • Calendar Last Updated On: Nov 6, 2009
Minimum Rental One Month. Beautiful condo - new on the rental market. You’ll be so glad the owners have decided to share their piece of paradise!

Beautiful Private Oceanfront Executive Estate with Sugar Sand Beach, Heated Pool – Property 311833

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, beach, waterfront, pool
  • $4,300 - $4,800/week
  • Calendar Last Updated On: Nov 5, 2009
Ocean front executive retreat with overwhelming views of the Atlantic, large open verandas, 165 feet of private sandy beach, 15 x 30 seaside heated swimming pool, 37...

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 5, 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...

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 5, 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,...

The Snook House in Bonefish Bay – Property 178871

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, beach, waterfront, pool
  • $5,000 - $7,000/week
  • Calendar Last Updated On: Nov 4, 2009
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 sandy beach, boat...

Blue Water Retreat – Property 7019197

  • Islamorada rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, air-conditioning, balcony
  • Calendar Last Updated On: Nov 4, 2009
Minimum Rental 28 Days. Location, location, location! This home has it all – ocean side Lower Matecumbe location, condition and features.

Luxurious Islamorada Oceanfront Vacation Home- Casa Eroici – Property 179867

  • Islamorada rental - house, 4 bedrooms, sleeps 12, 4 bathrooms, 1 half bath, beach, pool
  • Calendar Last Updated On: Nov 4, 2009
Casa Eroici's ground floor offers an enormous gym, also with a pool table and jukebox. Just outside the gym lies the beach with a fabulous pool with spa, sun deck,...
SPECIAL OFFER! Discount $50.00 Off Weekly Rate November 11 - 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 3, 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...

Gorgeous Oceanfront with heated pool – Property 207249

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, pool
  • Calendar Last Updated On: Nov 3, 2009
Once you enter into the fenced yard, you have arrived in paradise!! Welcome to this private oceanfront estate. Upstairs, there are 2 bedrooms and 2 bathrooms and...

'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 3, 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...

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

  • Islamorada rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, jacuzzi
  • $830 - $1,250/week
  • Calendar Last Updated On: Nov 3, 2009
Immaculate 2 bedroom, 2 bathroom condo with breathtaking views of the Atlantic Ocean from the living room balcony. This condo boasts a queen bed in master bedroom, 2...
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