TOP 20 Best Luxury vacation condos in Islamorada, Florida

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.

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.

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.

Casa Rio Islamorada is a charming lodging institution located at 121 Sapodilla Drive in Islamorada, Florida. Nestled in the heart of the Florida Keys, this cozy retreat offers a peaceful and serene atmosphere for guests to relax and unwind. With comfortable accommodations and a welcoming staff, Casa Rio Islamorada is the perfect place to escape the hustle and bustle of everyday life. Whether you're looking for a romantic getaway or a family vacation, this hidden gem is sure to provide a memorable experience. Explore the beautiful surroundings, soak up the sun on the nearby beaches, or simply enjoy a leisurely stroll along the waterfront. Come and experience the laid-back charm of Casa Rio Islamorada for yourself.

Keys Condo is a premier real estate and travel agency located at 101 Gulfview Drive in Islamorada, Florida. Specializing in luxury condo rentals in the beautiful Florida Keys, Keys Condo offers a wide range of properties to suit every traveler's needs. Whether you are looking for a beachfront retreat or a cozy apartment in the heart of town, Keys Condo has the perfect accommodation for you. With exceptional customer service and a wealth of local knowledge, Keys Condo is your go-to destination for a memorable vacation experience in the stunning Florida Keys. Contact us today to book your dream getaway!

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.

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.

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.

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.

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.

Florida Keys Vacation Rentals Inc. is a premier real estate and travel agency located at 85996 Overseas Highway in Islamorada, Florida. Specializing in vacation rentals in the beautiful Florida Keys, our team is dedicated to helping clients find the perfect property for their getaway. Whether you're looking for a cozy beachfront cottage or a luxurious waterfront villa, we have a wide range of options to choose from. Let us help you make your dream vacation a reality in this tropical paradise. Contact us today to start planning your unforgettable trip to the Florida Keys.

Ocean Sotheby’s International Realty is a prestigious real estate agency located at 81888 Overseas Highway in Islamorada, Florida. We specialize in connecting buyers with truly extraordinary properties in the Florida Keys, including condos, houses, and homes for sale in Sunset Key, Marathon, Key Largo, Key West, and beyond. Our team takes pride in utilizing our extensive experience, resources, and global connections to match unique properties with discerning buyers who appreciate their special qualities. Stay up to date with the latest real estate news and insights from the most desirable neighborhoods in the area by checking out our blog. With our esteemed advertising partners, we are excited to showcase the best of The Florida Keys and help you find your perfect home away from home. Contact us at 305-712-8888 or email us at [email protected] to learn more about our services. Please note that this website is not the official website of Sotheby’s International Realty, Inc., and each office is independently owned and operated. Visit us at our additional locations in Marathon and Key West.

Executive Bay Club is a premier institution located at 87200 Overseas Highway in Islamorada, Florida. It offers a luxurious and exclusive experience for its members, featuring top-notch amenities and services. With stunning views of the surrounding area and access to a range of recreational activities, Executive Bay Club is the perfect destination for those seeking a high-end lifestyle in the heart of the Florida Keys. Whether you're looking to relax by the pool, enjoy a game of tennis, or indulge in gourmet dining, this institution has everything you need for a truly unforgettable experience.

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.

Coral Cove Rentals is a premier real estate and travel agency located at 81906 Overseas Highway in Islamorada, Florida. Specializing in vacation rentals, Coral Cove offers a wide range of luxurious properties for short-term stays in this beautiful tropical paradise. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious condo, Coral Cove Rentals has the perfect accommodation for your next getaway. With personalized service and attention to detail, our team is dedicated to providing you with a memorable and stress-free vacation experience. Contact us today to book your dream vacation rental in Islamorada!

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.

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.

Pineapple Beach is a premier real estate and travel agency located at 130 Aregood Lane in the beautiful coastal town of Islamorada, Florida. Our team of experienced professionals is dedicated to helping clients find their dream beachfront property or plan the perfect tropical getaway. With a focus on personalized service and attention to detail, Pineapple Beach is committed to making your real estate or travel experience seamless and unforgettable. Contact us today to start your journey to paradise.

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.

The KeysListings Group at LoKation Real Estate, led by Jim Signor, is a premier real estate institution located at 4 Beach Road, Key Largo, Florida, United States. Established in 2003, KeysListings.com offers the best real estate search for homes and condos in the Florida Keys. The website is easy-to-use and updated every 5 minutes by the official Realtor’s database, the Florida Keys MLS. Visitors can create custom market reports to see active, under contract, and sold properties in their neighborhood and receive market updates on a weekly, bi-monthly, or monthly basis. The institution offers a variety of properties, from gorgeous homes in Key Largo to charming condos in Islamorada. With a focus on customer satisfaction and personalized service, The KeysListings Group at LoKation Real Estate is your go-to source for real estate in the Florida Keys.

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.

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.

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.

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 140 Rental is a real estate and travel agency located at 140 Anglers Way in Islamorada, Florida, United States. This stunning property offers 3 bedrooms, 2.5 baths, and breathtaking oceanfront views. Guests can enjoy huge decks, optional boat slips, and a gated community for added security. Located in the heart of Islamorada, guests have access to a variety of dining, activities, and shopping options. Whether you're looking to relax on the beach or explore the vibrant local culture, this property has something for everyone.