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Directory of Islamorada Vacation Rentals

Book your Islamorada accommodations now!

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  • LA SIESTA RESORT & VILLAS
  • 80241 Overseas Hwy Mile Marker 80.2 Oceanside Islamorada FL 33036
  • (888) 313-6200   E-mail Website
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  • This oceanfront resort on the sunrise side of Islamorada features beachfront cottages, private villas & suites. Enjoy our poolside bar, bikes, paddleboards & kayaks. Resort guests receive access to all four Islamorada Resorts & a complimentary shuttle.
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  • Osprey Bay Villa
  • 82754 Overseas Highway Islamorada FL 33036
  • (305) 393-2995 E-mail Website
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  • Wonderful Bay front home in the heart of Islamorada for rent by the week or month, sleeps 10. Spectacular sunsets & incredible panoramic views of Florida Bay! Walk to restaurants & shopping. Enjoy private pool, hot tub, beach, dockage/boat basin & more!
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  • CASITAS AT CHEECA LODGE
  • 81801 Overseas Hwy Islamorada FL 33036
  • (844) 489-9664   (305) 664-4651 E-mail Website
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  • NEW!! Luxurious one and two-bedroom Casitas located in the heart of Islamorada. Private sandy beach and pool. Guests have full access to the legendary Cheeca Lodge & Spa amenities. Your luxury Casita experience includes butler service.
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  • FLORIDA KEYS BREWING CO. B&B
  • 81611 Old Highway Islamorada FL 33036
  • (305) 664-9722 E-mail Website
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  • Stay in the heart of the Keys in our island shabby chic 2 bed/1 bath apartment above Florida Keys Brewing Co. Taproom. Walk/bike to the best restaurants, bars, shops & fishing Islamorada has to offer. Affordable, family/pet friendly in the best location!
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  • FLORIDA KEYS VACATION RENTALS, INC.
  • 85996 Overseas Hwy Islamorada FL 33036
  • (800) 207-4160   (305) 664-4470 E-mail Website
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  • Hundreds of homes, condos, townhomes & cottages located between Key Largo & Key West, most with waterfront locations. Preview them on our website & chat online or let our rental managers help you find your ideal vacation spot. Weekly & monthly rentals.
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  • Keys Holiday Rentals, INC
  • 83247 Overseas Highway Islamorada FL 33036
  • (305) 664-8808
  • Tarpon Oasis
  • 236 Tarpon Street Islamorada FL 33070
  • (561) 504-2640
  • Vacation Properties in the Florida Keys
  • 91495 Overseas Highway Tavernier FL 33070
  • (888) 464-3133
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