TOP 30 Florida vacation homes in Islamorada, Florida

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Robbie's of Islamorada is a Keys-style waterfront Restaurant and Bar located at 77522 Overseas Highway in Islamorada, Florida. Offering scenic views and a tropical atmosphere, Robbie's is a popular tourist attraction and travel agency for those looking to explore the Florida Keys. Home to the world-famous tarpon feeding, visitors can hand-feed massive tarpon, enjoy water sports, and shop for handcrafted souvenirs at the local shops. The restaurant serves fresh seafood and signature cocktails on the waterfront deck, while also offering a clothing store with a unique range of beachwear. Robbie's also provides yacht charters, snorkeling trips, fishing excursions, sunset cruises, and eco-tours to experience the beauty of the Florida Bay. With a variety of activities and amenities available, Robbie's of Islamorada is the perfect destination for a fun and memorable vacation in the Florida Keys.

IVs in the Keys is a health spa institution located at 81011 Overseas Highway in Islamorada, Florida, United States. We offer a unique and effective way to achieve maximum vitality in just 30 minutes with our IV therapy treatments. Walk-ins are welcome at our locations in Key West and Islamorada. Our IV therapy delivers hydration and essential nutrients directly to your cells through the bloodstream, ensuring 100% absorption. Our experienced Registered Nurses, who are all ER-trained, work under the supervision of our Medical Director, Dr. Kris Bly. There are no co-pays, consult fees, or waiting for appointments at our facility.

Islamorada Vacation Rentals is a premier real estate agency located at 81610 Overseas Highway in Islamorada, Florida. Specializing in providing luxurious vacation rentals in the beautiful Florida Keys, our agency offers a wide range of properties to suit every traveler's needs. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious waterfront home, we have the perfect rental for your next getaway. Our dedicated team is committed to providing exceptional service and ensuring that your vacation in Islamorada is unforgettable. Book with us today and experience the ultimate in relaxation and luxury.

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.

Buy Florida Keys Property is a finance and real estate agency located at 285 Jasmine Street in Tavernier, Florida. Specializing in Florida Keys short sales, the institution helps both borrowers and lenders navigate the process of selling real estate when the sale proceeds fall short of the loan balance. By avoiding foreclosure, both parties can mitigate financial losses and maintain credit history. Additionally, Buy Florida Keys Property offers services related to foreclosures, providing information on the legal and professional proceedings involved in repossessing a property due to default on a mortgage. The agency also offers services for buying and selling residential properties in Islamorada, Key Largo, and other Florida Keys communities, with a focus on maximizing resale value and choosing a location with economic stability and desirable community amenities. Whether looking to purchase a dream home or vacation property, Buy Florida Keys Property is dedicated to helping clients find the perfect real estate solution in the Florida Keys.

Islamorada Vacation Rentals is a premier real estate and travel agency located in the picturesque town of Islamorada, Florida. Situated at 109 Columbus Drive, our agency specializes in providing luxurious vacation rentals for those looking to experience the beauty and charm of the Florida Keys. From waterfront villas to cozy beachfront cottages, we offer a wide range of accommodation options to suit every traveler's needs. Our dedicated team of professionals is committed to ensuring that your stay in Islamorada is unforgettable, providing top-notch customer service and expert advice on local attractions and activities. Whether you're looking for a romantic getaway or a family vacation, Islamorada Vacation Rentals is your go-to destination for the perfect tropical retreat.

SuCasa Vacation Rentals is a charming lodging institution located at 77360 Overseas Highway in the picturesque town of Islamorada, Florida. Offering a variety of vacation rental options, SuCasa provides guests with a home away from home experience in the heart of the Florida Keys. Whether you are looking for a cozy cottage by the beach or a luxurious waterfront villa, SuCasa has the perfect accommodation for your vacation needs. With top-notch amenities, personalized service, and a convenient location near local attractions and activities, SuCasa Vacation Rentals is the ideal choice for a memorable stay in Islamorada.

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 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 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.

Freewheeler Vacations is a premier real estate and travel agency located in the beautiful coastal town of Islamorada, Florida. Our team of experienced professionals specialize in helping clients find their dream vacation rental or investment property in this stunning tropical paradise. Whether you're looking for a luxurious beachfront villa or a cozy cottage by the water, we have the expertise to make your vacation dreams a reality. Come visit us at 85992 Overseas Highway and let us help you plan the perfect getaway in the Florida Keys.

Amy Bruggeman Realtor is a premier real estate agency located in Key Largo, Florida, specializing in properties in the beautiful coastal town of Islamorada. With a prime location at 99900 Overseas Highway, Amy Bruggeman Realtor offers a wide range of services to assist clients in buying or selling their dream homes in this stunning waterfront community. Whether you are looking for a beachfront villa, a luxury condo, or a charming vacation home, Amy Bruggeman Realtor has the expertise and local knowledge to help you find the perfect property. Trust Amy Bruggeman Realtor to make your real estate dreams a reality in Key Largo and Islamorada.

Venetian Shores Islamorada Fl is a premier real estate agency located at 85996 Overseas Highway in Islamorada, Florida. Specializing in luxury waterfront properties, this institution offers unparalleled service and expertise in the vibrant and sought-after community of Venetian Shores. With a team of experienced and knowledgeable real estate professionals, Venetian Shores Islamorada Fl is dedicated to helping clients find their dream home or investment property in this picturesque and exclusive neighborhood. Whether you are looking for a waterfront estate, a vacation rental, or a charming bungalow, Venetian Shores Islamorada Fl has the resources and connections to make your real estate goals a reality. Contact them today to start your journey towards owning a piece of paradise in the beautiful Florida Keys.

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.

Jamie Engel & The Florida Keys Home Team Realtors is a premier real estate agency located at 85996 Overseas Highway in Islamorada, Florida. Specializing in luxury homes in the beautiful Florida Keys, our team of experienced professionals is dedicated to helping clients buy and sell their dream properties. From Key Largo to Key West, we are here to assist with all your real estate needs. With over 17 years of experience in the Florida Keys market, we understand the unique challenges and rewards of buying and selling property in this special area. Our team stays ahead of the curve by keeping up with the latest trends in luxury real estate, utilizing cutting-edge marketing techniques, internet technology, and social media to help clients make informed decisions.

Coastal Realty of the Florida Keys is a premier real estate agency located at 82889 Overseas Highway in Islamorada, Florida. Specializing in properties in the beautiful Florida Keys, this agency offers a wide range of services to help clients buy, sell, or rent their dream homes or vacation properties in this stunning coastal region. With a team of experienced and knowledgeable real estate professionals, Coastal Realty of the Florida Keys is dedicated to providing exceptional service and helping clients find the perfect property to suit their needs and preferences. Whether you are looking for a waterfront home, a luxury condo, or a charming beachfront cottage, this agency has the expertise and resources to make your real estate dreams a reality. Contact Coastal Realty of the Florida Keys today to start your property search in this tropical paradise.

Old Hwy 90515 Islamorada is a reputable real estate and travel agency located in Tavernier, Florida. Situated at 90515 Old Highway, this institution offers a wide range of services to assist clients in buying, selling, or renting properties in the beautiful Islamorada area. Additionally, they provide expert travel planning services for those looking to explore the stunning surroundings of the Florida Keys. With a dedicated team of professionals and a prime location, Old Hwy 90515 Islamorada is the go-to destination for all your real estate and travel needs in the Tavernier area.

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 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.

Located at 81200 Overseas Highway in Islamorada, Florida, the Kon-Tiki Resort is a charming lodging institution that offers a unique and unforgettable vacation experience. Nestled in the heart of Islamorada, our resort boasts fully-equipped villa accommodations and an unbeatable location on the Florida Bay, making it the perfect destination for those seeking a relaxing getaway. With 23 unit accommodations to choose from, each with its own unique flair, guests can enjoy a range of options including standard rooms, spacious efficiency apartments, and villas complete with a kitchen, living room, and dining area. Our accommodations are designed to provide ultimate comfort and style for our guests.

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.

Jill Of All Trades Cleaning Inc is a premier house cleaning service located at 97300 Overseas Highway in Key Largo, Florida. Since 2007, we have been providing top-notch cleaning services for homes, vacation rentals, and commercial properties in the Florida Keys. Our experienced team offers a range of services including move in move out cleaning, construction cleaning, deep cleaning, and emergency cleaning. Whether you need a one-time cleaning or regular maintenance, we offer flexible scheduling options to suit your needs. Our licensed and insured team serves clients in Key Largo, Tavernier, Islamorada, Long Key, Duck Key, Marathon, Big Pine Key, Summerland Key, and Key West.

Island Villa Rental Properties is a premier real estate and travel agency located at 81681 Old Highway in Islamorada, Florida, United States. Specializing in luxurious vacation rentals on the beautiful islands of Islamorada, our agency offers a wide selection of stunning villas and properties for visitors looking to experience the ultimate island getaway. With top-notch customer service and a team of experienced professionals, Island Villa Rental Properties is dedicated to helping clients find their perfect vacation rental in this tropical paradise. Whether you're looking for a romantic beachfront villa or a spacious family-friendly property, we have something for everyone. Book your dream vacation with us today and let us help you create unforgettable memories in the Florida Keys.

Rich Trottnow is a real estate agency located at 81579 Old Highway in Islamorada, Florida, United States. Specializing in upscale homes and condos with spectacular views and amenities, Island Management, owned by Judy Rossignol, offers top-notch customer service and attention to detail for both renters and homeowners. With a team of experienced agents, including Rich Trottnow, clients can trust that their property will be well cared for in their absence. Whether you are looking to rent a vacation home for a week or longer, or seeking to maximize the return on your investment property, Island Management is the perfect choice. Additionally, Judy Rossignol and her team at Realty One Group Engage the Keys are available to assist with buying or selling real estate in the Florida Keys. Contact Island Management today to find your next vacation home or discuss property management options.

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.

Little Basin Villas is a premier real estate and travel agency located in the picturesque Islamorada, Florida. Situated at 84 Johnston Road, our institution offers luxurious villas for rent or purchase in this stunning seaside town. Whether you are looking for a vacation rental or a permanent residence, our team of experts is dedicated to helping you find the perfect property to suit your needs. With a focus on personalized service and attention to detail, Little Basin Villas is the ideal choice for those seeking a slice of paradise in the Florida Keys. Contact us today to start your journey towards owning or renting your dream villa in Islamorada.

American Caribbean Real Estate is a premier real estate agency located at 81800 Overseas Highway in Islamorada, Florida. With over 30 years of experience in the Florida Keys real estate market, we have built a reputation for integrity, professionalism, and unparalleled market expertise. Our two locations in Islamorada and Key Largo cater to buyers and sellers looking for the perfect property in the Keys. As an industry leader in the Florida Keys marketplace, we have closed billions of dollars in sales and listings. Our dedicated sales team and administrative staff are committed to exceeding the expectations of our clients. One of our unique strengths is our affiliation with Christie's International Real Estate, the world's luxury real estate leader. This affiliation recognizes our superb performance in marketing and selling the most prized residences in the Florida Keys.

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.

KeysVacationHouse.com is a premier real estate and travel agency located at 88005 Overseas Highway in Islamorada, Florida. Specializing in luxurious vacation rentals in the beautiful Florida Keys, our agency offers a wide selection of stunning properties for visitors to choose from. Whether you are looking for a cozy beachfront cottage or a spacious waterfront villa, we have the perfect vacation house to suit your needs. Our team of experienced agents is dedicated to providing exceptional customer service and helping you find the ideal accommodation for your dream getaway. Book your next vacation with KeysVacationHouse.com and experience the ultimate in comfort and relaxation in the tropical paradise of the Florida Keys.

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.