Islamorada Florida Vacation Rentals and Vacation Homes

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Barefeet Rentals
 Toll Free 877-214-9590 
Key Largo, Florida Barefeet Rentals is located in the Upper Florida Keys on the island of Key Largo and only a short drive to Islamorada, surrounded by the azure waters to the east of the Atlantic Ocean and ...
Browse 37 Vacation Rentals

Keys Holiday Rentals
 305-664-8808 
Are you looking for an experienced rental specialist who knows the Islamorada and the Upper Keys Rental Market and can get the results you desire? Let me put my knowledge, experience, and dedication to work f...
Browse 44 Vacation Rentals

Rentalsfloridakeys.com
 305-743-5181, 888-743-5635 
Florida Keys Vacation Rentals manages hundreds of vacation rental properties ranging from luxurious to budget-conscious throughout The Florida Keys including Key West, the Lower Keys, the Middle Keys, Islamor...
Browse 321 Vacation Rentals

 86 Rentals in Islamorada

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Property 76665

Islamorada 2 in the Florida Ke

  • Islamorada 2 in the Florida Keys - This Is Pure Luxury in The Keys!
  • Villa in Islamorada
  • 5 Bedroom(s)
  • Weekly Rates from $10,000
Property 89709

IS534 - San Marco Retreat

  • IS534 - San Marco Retreat
  • Home in Islamorada
  • 5 Bedroom(s)
  • 4 Bathroom(s)
Property 89716

IS545 - Sunset Dream

  • IS545 - Sunset Dream
  • Home in Islamorada
  • 5 Bedroom(s)
  • 4 Bathroom(s)
Property 6863

The PERFECT Getaway

  • Islamorada 4BR Vacation Home - The Perfect Getaway with Heated Pool and Jacuzzi - IN THE HEART of ISLAMORADA
  • House in Islamorada
  • 4 Bedroom(s), Sleeps 8-10
  • 3 Bathroom(s)
  • Weekly Rates from $2,000
Property 40870

Tavernier Vacation Rental Home

  • Ocean Front.....Two houses for the price of One
  • House in Islamorada (Near Tavernier)
  • 4 Bedroom(s), Sleeps 13
  • 4 Bathroom(s)
  • Weekly Rates from $1,900
Property 59460

Serenity Bay

  • Serenity Bay
  • House in Key Largo (Near Islamorada)
  • 4 Bedroom(s), Sleeps 12
  • 3 Bathroom(s)
Property 59461

525 Mariner's Club

  • 525 Mariner's Club
  • Condo in Key Largo (Near Islamorada)
  • 4 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
  • Weekly Rates from $2,750
Property 82074

Emerald Cove

  • House in Islamorada (Near Lower Matecumbe)
  • 4 Bedroom(s), Sleeps 8 - 10
  • 3 Bathroom(s)
Property 89702

IS220 - Sunset on Beach

  • IS220 - Sunset on Beach
  • Home in Islamorada
  • 4 Bedroom(s)
  • 3 Bathroom(s)
Property 89704

IS508 - Fisherman's Dream

  • IS508 - Fisherman's Dream
  • Home in Islamorada
  • 4 Bedroom(s)
  • 4 Bathroom(s)
Property 89714

IS543 - Tarpon House

  • IS543 - Tarpon House
  • Home in Islamorada
  • 4 Bedroom(s)
  • 5 Bathroom(s)
Property 89723

IS568 - Atlantic Fishin

  • IS568 - Atlantic Fishin
  • Home in Islamorada
  • 4 Bedroom(s)
  • 3 Bathroom(s)
Property 53777

Blue Water Retreat

  • Ocean Side Blue Water Retreat House!!
  • House in Islamorada
  • 3 Bedroom(s), Sleeps 6-8
  • 3 Bathroom(s)
Property 53780

My Paradise

  • Oceanfront Paradise
  • House in Islamorada
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
Property 53782

Venetian Dream Home

  • Venetian Dream Home - Located in the heart of Islamorada!!
  • House in Islamorada
  • 3 Bedroom(s), Sleeps 6-8
  • 4.5 Bathroom(s)
Property 53783

Valencia Getaway

  • Valencia Getaway Islamorada FL Vacation Rentals
  • House in Islamorada
  • 3 Bedroom(s), Sleeps 6-8
  • 2 Bathroom(s)
Property 53785

Mermaid's Cottage

  • Mermaid's Cottage
  • House in Islamorada
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
Property 53834

Matecumbe Jewel

  • Relax by the Pool at this Vacation Jewel !!
  • House in Islamorada
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
Property 59448

501 Futura Yacht Club

  • 501 Futura Yacht Club
  • Condo in Islamorada (Near Tavernier )
  • 3 Bedroom(s), Sleeps 7
  • 2 Bathroom(s)
Property 59450

Villa 13

  • Villa 13
  • Villa in Key Largo (Near Islamorada)
  • 3 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
Property 59451

The Fishing Lodge

  • The Fishing Lodge
  • House in Tavernier (Near Islamorada)
  • 3 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
  • Weekly Rates from $1,872
Property 59453

410 Mariner's Club

  • 410 Mariner's Club
  • Resort in Key Largo (Near Islamorada)
  • 3 Bedroom(s), Sleeps 6
  • 3 Bathroom(s)
Property 59454

407 Mariner's Club

  • 407 Mariner's Club
  • Resort in Key Largo (Near Islamorada)
  • 3 Bedroom(s), Sleeps 8
  • 3 Bathroom(s)
Property 59455

131 Mariner's Club

  • 131 Mariner's Club
  • Resort in Key Largo (Near Islamorada)
  • 3 Bedroom(s), Sleeps 10
  • 3 Bathroom(s)
Property 59456

E-24 Coral Harbor Club

  • E-24 Coral Harbor Club
  • Condo in Key Largo (Near Islamorada)
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)


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