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

Vacation Rentals in Islamorada

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Boat, Fish, Swim from Your Own Dock! – Property 158981

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 1 bathroom, near the ocean, waterfront, accept credit card
  • Calendar Last Updated On: Jul 19, 2008
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...

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

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, beach, near the ocean, swimming pool
  • $2,100 - $2,400/week
  • Calendar Last Updated On: Jul 17, 2008
Boater's paradise is a beautiful canal front home with swimming pool, 4 bedroom/2 bathrooms, sleeps 8 in the famous Florida Keys.

Beautiful Captain's Cove – Property 218650

  • Islamorada rental - villa, 3 bedrooms, sleeps 8, 2 bathrooms, beach, waterfront, air-conditioning
  • Calendar Last Updated On: Jul 17, 2008
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.

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

  • Islamorada rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $1,110 - $1,250/week
  • Calendar Last Updated On: Jul 17, 2008
Immaculate 2 bedroom, 2 bathroom condo with breathtaking views of the Atlantic Ocean from the living room balcony. This condo boasts jacuzzi tubs in both bathrooms,...

Bonefish Bay: Islamorada Luxury Home with Resort Amenities – Property 152005

  • Islamorada rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, 1 half bath, beach, waterfront, swimming pool
  • $5,000 - $6,000/week
  • Calendar Last Updated On: Jul 14, 2008
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 resort.

New Luxurious Bay Harbour Waterfront Condo, 2 Master Bedrooms w/Private Baths – Property 321060

  • Islamorada rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, waterfront, swimming pool
  • $1,500 - $2,000/week
  • Calendar Last Updated On: Jul 15, 2008
You will feel as if you have stepped into the pages of 'Coastal Living' magazine when you step into your Florida Keys Islamorada vacation home.

Beautiful New Waterfront Home In Port Antigua – Property 178832

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, near the ocean, waterfront, swimming pool
  • $2,300/week
  • Calendar Last Updated On: Jul 10, 2008
This beautiful new home is furnished with a TV in each bedroom. Granite countertops in kitchen and bathrooms with stailess steel appliances.

Venetian Tropics, Islamorada Florida Keys, on deep canal and pool – Property 204162

  • Islamorada rental - house, 2 bedrooms, sleeps 8, 2 bathrooms, waterfront, swimming pool
  • $2,200/week
  • Calendar Last Updated On: Jul 10, 2008
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...

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

  • Islamorada rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, waterfront, swimming pool
  • $950 - $1,600/week
  • Calendar Last Updated On: Jul 12, 2008
Florida Keys 5th floor end unit directly on the ocean in lovely Islamorada. Enjoy beautiful panoramic ocean views from this bright and comfy unit, 1,200 sq.

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

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, air-conditioning
  • Calendar Last Updated On: Jul 8, 2008
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...

New Home with Key West Charm – Property 142257

  • Islamorada rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, near the ocean, village, swimming pool
  • Calendar Last Updated On: Jul 8, 2008
'Caddy Corners' is a charming Key West style three-bedroom, two-bath home located in the heart of Islamorada on the Florida Keys.

Vacation Home with Cheeca Lodge and Spa Guest Pass - Crooked Corners – Property 220594

  • Islamorada rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, near the ocean, village, swimming pool
  • Calendar Last Updated On: Jul 8, 2008
Crooked Corners is a charming Key West Style three-bedroom, two-bath home located in the heart of Islamorada on the Florida Keys.
SPECIAL OFFER! August Availability 20% off reg Price August 9 - August 30

Oceanfront Mansion – Property 104448

  • Islamorada rental - house, 10 bedrooms, sleeps 20, 6 bathrooms, 1 half bath, town, waterfront, accept credit card
  • Calendar Last Updated On: Jul 6, 2008
The Florida Keys Largest, most Prestigious Vacation Rental Home Available! Vacation in your own private Oceanfront Mansion in the Florida Keys!

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

  • Islamorada rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, beach, waterfront, swimming pool
  • $3,500 - $4,300/week
  • Calendar Last Updated On: Jul 6, 2008
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...

Quiet Open Water Hideaway On Wildlife Preserve – Property 183894

  • Islamorada rental - villa, 2 bedrooms, sleeps 4, 1 bathroom, beach, waterfront, accept credit card
  • $1,200 - $1,400/week
  • Calendar Last Updated On: Jul 5, 2008
Relax in this peaceful, open-water bird and wildlife sanctuary. In a living room only 9 feet from water's edge, you can sit on your sofa and watch fish swim.

Futura Yacht Club Condominium Unit – Property 301565

  • Islamorada rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $750 - $1,150/week
  • Calendar Last Updated On: Jul 4, 2008
Two privately owned condominium units at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex...

New Beautiful Ocean View Bay Harbour Condo with Deep Water Dock – Property 318327

  • Islamorada rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, swimming pool, air-conditioning
  • Calendar Last Updated On: Jul 3, 2008
Gorgeous new Bay Harbour gated condo community on Lower Matecumbe, MM 74 1/2.Lush tropical landscaping, heated pool with jetted spa, two lighted tennis courts, club...
SPECIAL OFFER! 1000.00 off regular weekly rate August 9 - November 15

La Casa Grande – Property 173152

  • Islamorada rental - estate, 6 bedrooms, sleeps 12, 6 bathrooms, 2 half baths, beach, near the ocean, accept credit card
  • $7,500/week
  • Calendar Last Updated On: Jul 1, 2008
La Casa Grande is a beautiful three story home located in the famous Florida Keys. This luxurious home features ocean views from most rooms, a swimming pool,...

Prestigious Venetian Shores! – Property 168242

  • Islamorada rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, accept credit card
  • $1,664/week
  • Calendar Last Updated On: Jul 1, 2008
What a special place to vacation! This ground level three bedroom, two bath home underwent a major renovation in 2007! Large open floor plan with tile floors...

Islamorada - Florida Keys - Dockage included! – Property 163762

  • Islamorada rental - condo, 3 bedrooms, sleeps 7, 2 bathrooms, near the ocean, waterfront, accept credit card
  • $1,040/week
  • Calendar Last Updated On: Jul 1, 2008
Bay front complex in sunny Islamorada! A private 70 unit community with heated pool, tennis court and sunning beach. This three bedroom, two bath condo offers...
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