TOP 30 Rental spaces in Islamorada, Florida

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Located at 81801 Overseas Highway in Islamorada, Florida, Cheeca Lodge & Spa offers a luxurious retreat surrounded by turquoise waters, towering palms, and calm breezes. This oceanfront resort invites guests to experience barefoot luxury and embrace the laid-back lifestyle of the Florida Keys. With a range of thrilling activities, luxurious accommodations, exceptional dining options, and unparalleled relaxation, Cheeca Lodge & Spa promises an unforgettable getaway. Whether you're looking to celebrate love with a picturesque oceanfront wedding or host a productive corporate retreat, Cheeca Lodge & Spa offers the perfect venue. With over 15,000 square feet of meeting space, impeccable service from event planners, and a stunning backdrop of the Atlantic ocean, this resort is ideal for weddings, sales meetings, conferences, and more.

Located at 80241 Overseas Highway in Islamorada, Florida, La Siesta Resort & Villas offers a tropical island style getaway with spacious guest rooms, beachside cottages, and private vacation homes. Experience authentic Keys life with island-inspired flavors and legendary cocktails while enjoying stunning sea views. The resort features lush private beaches, pools with ocean views, and fishing charters for the catch of your dreams. Accommodations include suites, cottages, and villas with idyllic Islamorada views and unique resort amenities. Special offers include discounts for Florida and Georgia residents, military personnel, and tax season rewards. Enjoy dining at Wild & Lime and nearby restaurants, as well as unforgettable experiences for special occasions. Plan your dream destination wedding or arrive at the Florida Keys marina for a seamless vacation experience. Explore all that La Siesta Resort & Villas has to offer and make memories to last a lifetime.

Tea Table Key Island Estate & Wedding Venue is a luxurious and exclusive private island located in Islamorada, Florida. This stunning Caribbean island is accessible by car and offers unparalleled privacy and beauty. The estate features a 5 bedroom main home, separate living quarters, pool, cabana, dockage, helipad, and tennis court. With floor to ceiling windows and wraparound views, the main home provides a truly immersive experience of the surrounding waters and Alligator Reef Light. The expansive master bedroom on the second floor offers breathtaking sunrises and sunsets from every window and patio. This vacation rental is available for $25,000 - $35,000 weekly, with additional fees for holiday weddings and events. To inquire about booking this extraordinary property, contact (305) 664-3333 or email rentals@islandvilla.com.

Welcome to Treasure Key Realty, your premier destination for real estate excellence in Cape Coral, Florida. Located at 1102 Southeast 21st Avenue, our agency is dedicated to helping you find your dream property or sell your home for top dollar. Led by Tara Brommer, a seasoned REALTOR® and Broker-Owner, our team is committed to providing clear, concise, and no-nonsense communication to ensure a seamless real estate experience for our clients. At Treasure Key Realty, we specialize in showcasing extraordinary properties in our featured areas, including the stunning Florida Keys. Whether you're dreaming of constructing a luxury residence on expansive acreage or seeking a charming home in the heart of Cape Coral, we have the expertise and resources to make your real estate goals a reality.