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TOP 30 Rental homes with pools in Islamorada, FL
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Anglers Reef Vacation Rental
Anglers Reef Vacation Rental is a premier real estate and travel agency located at 109 Anglers Way in Islamorada, Florida. Our vacation rentals offer luxurious accommodations in a picturesque setting, perfect for those looking to escape and unwind in the beautiful Florida Keys. From cozy beachfront cottages to spacious waterfront villas, we have a variety of options to suit every traveler's needs. Our friendly and knowledgeable staff is dedicated to providing top-notch service and ensuring a memorable stay for all our guests. Experience the ultimate tropical getaway at Anglers Reef Vacation Rental.
Barefeet Vacation Rentals
Barefeet Vacation Rentals is a real estate and travel agency located at 103400 Overseas Highway in Key Largo, Florida. Specializing in Key Largo and Islamorada vacation rentals, Barefeet Rentals offers a variety of private homes and condos to fit any budget, some even featuring docks for boaters. Whether you're a boater, fisherman, scuba diver, sun worshiper, or snowbird, Barefeet Rentals has something for everyone in the fabulous Florida Keys. From snorkeling coral reefs to deep-sea fishing excursions, there are endless activities to enjoy in this tropical paradise. Explore the Everglades National Park on an airboat tour or kayak through the Florida Keys for a unique eco-adventure.
Islamorada Vacation Rental
Islamorada Vacation Rental is a premier lodging option located at 101 Leoni Drive in Islamorada, Florida. As a combination of a real estate agency and travel agency, we specialize in providing top-quality vacation rentals for visitors looking to experience the beauty and charm of the Florida Keys. Our properties offer a range of amenities and locations, ensuring that guests have a comfortable and memorable stay. Whether you're looking for a beachfront villa, a cozy cottage, or a luxurious waterfront home, Islamorada Vacation Rental has the perfect option for you. Book with us today and start planning your dream vacation in paradise.
Coastal Vacation Rentals of the Florida Keys
Coastal Vacation Rentals of the Florida Keys is a premier real estate and travel agency located at 82889 Overseas Highway in Islamorada, Florida, United States. We specialize in luxury vacation homes that exceed your expectations and cater to all your needs. Our extensive inventory includes weekly and monthly rentals, condos, villas, estates, corporate retreats, oceanfront and bayfront properties. Our personalized service sets us apart, ensuring that your vacation is a success no matter where you choose to stay in the Florida Keys. From breathtaking views to top-notch amenities, we have everything you need for a memorable getaway. Whether you're looking for a romantic escape or a family adventure, we have something for everyone.
La Siesta Resort & Villas
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.
KeysCaribbean Resorts
KeysCaribbean Resorts is a premier lodging institution located at 97501 Overseas Highway in Key Largo, Florida, United States. Our team of professional agents is available 24 hours a day to ensure a stress-free and exceptional vacation experience for our guests. Choose from our select rentals at premier Upper & Middle Keys resort communities, where you'll have exclusive access to top-notch amenities such as private swimming pools, boat dockage, Jacuzzi tubs, and more. Whether you're planning a family reunion or a getaway with friends, we can accommodate your needs with our range of rental options.
Anglers Reef Villas
Anglers Reef Villas is a luxurious waterfront lodging option located at 110 Anglers Way in Islamorada, Florida. As a combination of a lodging, real estate, and travel agency, Anglers Reef Villas offers guests the opportunity to experience the ultimate vacation in paradise. With stunning views of the ocean, top-notch amenities, and a prime location near popular attractions, Anglers Reef Villas is the perfect choice for those seeking a memorable stay in the Florida Keys. Whether you're looking to relax on the beach, explore the local area, or invest in a vacation home, Anglers Reef Villas has everything you need for a truly unforgettable experience.
Lignumvitae Key Botanical State Park
Lignumvitae Key Botanical State Park is a stunning park and tourist attraction located at 77200 Overseas Highway in Islamorada, Florida, United States. The park features a beautiful tropical hardwood hammock that was once common in the Upper Keys of Florida. In 1919, William J. Matheson, a wealthy Miami chemist, purchased the island and built a caretaker's home with unique amenities such as a windmill for electricity and a cistern for rainwater. Today, visitors can explore his historic hideaway, which now serves as the visitor center for the park.
Heart of Morada
The Heart of Morada is a unique institution located at 81906 Overseas Highway in Islamorada, Florida. As a real estate agency, we specialize in helping clients find their dream homes in this beautiful coastal town. Our team of experienced agents is dedicated to providing personalized service and expert guidance throughout the buying or selling process. In addition to our real estate services, we also operate as a travel agency, offering vacation rental properties and booking assistance for those looking to explore all that Islamorada has to offer. Whether you're searching for a permanent residence or a temporary getaway, the Heart of Morada is here to help you find the perfect property to suit your needs.
The Beach House at Tarpon Point
The Beach House at Tarpon Point is a luxurious oceanfront home located at 77521 Overseas Highway in Islamorada, Florida. This stunning property offers amazing ocean views, a sandy beach, pool, and an observation pier perfect for watching sunrises and sunsets. As a real estate and travel agency, The Beach House provides top-notch amenities and furnishings to ensure a relaxing and memorable vacation experience for all guests. Whether you're looking for a peaceful retreat or a fun-filled getaway, The Beach House at Tarpon Point is the perfect destination for your next trip to the beautiful Florida Keys.
The "Nest" Villa
Welcome to The "Nest" Villa, located at 82236 Overseas Highway in Islamorada, Florida. Our villa is the perfect home away from home for your next Florida Keys vacation. Situated in a central part of Islamorada, our property is close to local attractions, shops, bars, and restaurants, many of which are within walking distance. Our villa is one of only seven units on the property, nestled on a shaded one-acre tropical hammock that stretches from the highway down to the beautiful shores of Florida Bay. The villa is secluded and private, with stunning views of the water and spectacular sunsets.
Beacon Reef Condominiums
Beacon Reef Condominiums is a luxurious waterfront property located at 83201 Old Highway in Islamorada, Florida. These stunning condominiums offer breathtaking views of the ocean and are surrounded by lush tropical landscaping. Residents can enjoy resort-style amenities such as a pool, fitness center, and private beach access. The spacious units feature modern finishes and open floor plans, perfect for entertaining guests or relaxing in style. With its prime location in the heart of the Florida Keys, Beacon Reef Condominiums is the perfect place to call home for those seeking a peaceful and upscale coastal lifestyle.
Latitude Key Vacations
Latitude Key Vacations is a premier real estate and travel agency located at 3324 Northeast 32nd Street in Fort Lauderdale, Florida, United States. Specializing in curating vacation properties across three collections - Villas, Residences, and Homes - our properties are situated in high-end, quiet neighborhoods in Fort Lauderdale, Pompano Beach, Lauderdale-by-the-Sea, West Palm Beach, Islamorada (The Keys), Hollywood, and Delray Beach. We pride ourselves on offering meticulously equipped accommodations with lavish linens, opulent towels, natural Pure Fiji toiletries, and convenient starter kits. Our commitment to providing a perfect vacation experience includes round-the-clock support and additional services to elevate your stay. Our expertly designed villas boast high-end amenities and waterfront tranquility, providing the ultimate vacation experience. Floridian style residences feature heated pools in backyards with lounge areas, ideal for a serene getaway. Explore the unique charm of Fort Lauderdale, Hollywood, Lauderdale-By-The-Sea, Pompano Beach, West Palm Beach, and Delray Beach through our range of properties located in these vibrant destinations. Whether you prefer a beachfront property or a city center location, we offer a variety of accommodations to suit your needs.
Tea Table Key Island Estate & Wedding Venue
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.
Treasure Key Realty
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.
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