TOP 30 Key west vacation rentals in Florida

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Disney's Old Key West Resort is a luxurious lodging option located at 1510 North Cove Road in Lake Buena Vista, Florida, United States. This resort offers Disney Deluxe Villas with all the comforts of home, including a kitchen, washer, dryer, and separate bedrooms. Ideal for families and larger parties, these accommodations come in 1-Bedroom, 2-Bedroom, and 3-Bedroom options. Guests can enjoy amenities such as a sandcastle waterslide, dry sauna, whirlpool spa, and sand beach. There are multiple pools on the property, including a 149,000-gallon main pool and three quiet pools with whirlpool spas. The resort also features a state-of-the-art fitness center and sauna for guests to enjoy.

Located in Key Largo, Florida, the Key Lime Sailing Club and Cottages offers a unique and tranquil waterfront lodging experience. Our self-contained cottages provide everything you need for a relaxing getaway, with no hidden charges. Enjoy the beautiful sunsets from our intimate setting, or explore the local dining and dancing options just a short walk or paddle away. Easy to reach but hard to forget, our hideaway is the perfect place to unwind and enjoy the beauty of the Florida Keys. Book your stay with us today and experience the magic of Key Largo.

Paddle the Florida Keys is a top-rated institution located in Tavernier, Florida, offering kayak and paddleboard rentals, eco-tours, sales, and deliveries. Whether you're a beginner or experienced paddler, our professional guides will lead you on an unforgettable journey through the beautiful mangrove tunnels and seagrass meadows of the Florida Keys. With flat rates and the option to rent for 24 hours or longer, you can paddle at your own pace and explore at your leisure. Owner Deven Carrier, a lifelong Keys local and competitive paddle board racer, is passionate about the sport and has helped grow the local paddlesport community for over a decade. Our retail store offers a wide selection of paddle boards, skateboards, gear, and accessories, ensuring you have everything you need for a day on the water or onshore.

Sail Key Largo is a premier travel agency located at 1313 Ocean Bay Drive in Key Largo, Florida. Specializing in sailing adventures and excursions, Sail Key Largo offers a wide range of services including yacht charters, sailing lessons, and guided tours of the stunning Florida Keys. Whether you are a seasoned sailor or a beginner looking to explore the open waters, Sail Key Largo has something for everyone. With a team of experienced sailors and knowledgeable staff, you can trust that your sailing experience with Sail Key Largo will be unforgettable. Plan your next sailing adventure with Sail Key Largo and discover the beauty of the Florida Keys from a whole new perspective.

The Key West Resort on Lake Dora in Tavares, Florida offers stylish accommodations and modern amenities for both leisure and business travelers. Situated in the Entertainment District, just steps away from the Lake County Courthouse, our hotel is conveniently located on the waterfront of Lake Dora. Each spacious room and suite features hardwood or tile floors, wet bars with essential appliances, and most offer private balconies with stunning views of the Seaplane Basin. As one of Florida's only inland seaplane basins, our resort attracts pilots and travelers alike looking for a unique experience. Nearby, guests can enjoy water sports rentals, lake cruises, and live entertainment at various waterfront venues. The on-site Tiki West Bar and Grille, Hemingway's Wine and Cigar Bar, and Shiner's Bar and Grille provide convenient dining options, while a complimentary continental breakfast is included with your stay.

Home2 Suites by Hilton Nokomis Sarasota Casey Key is a modern and stylish lodging option located at 227 Albee Road West in Nokomis, Florida. This hotel offers comfortable suites with fully equipped kitchens, spacious living areas, and complimentary Wi-Fi. Guests can enjoy amenities such as a fitness center, outdoor pool, and complimentary breakfast. The convenient location near Casey Key and Sarasota makes it a great choice for both leisure and business travelers looking for a relaxing stay in the Sunshine State.

Casey Key Beach Condos is a charming lodging institution located at 910 Lindis Lane in Nokomis, Florida, United States. Situated right by the beautiful Casey Key Beach, this institution offers luxurious and comfortable condos for guests looking for a relaxing beach getaway. With stunning ocean views, easy access to the beach, and a range of amenities, Casey Key Beach Condos is the perfect place to unwind and enjoy the sun, sand, and sea. Experience a truly unforgettable vacation at this idyllic beachfront retreat.

Beach Colony West Associates is a luxurious lodging institution located at 13601 Perdido Key Drive in Pensacola, Florida, United States. Situated right on the beautiful beaches of the Gulf Coast, this establishment offers stunning ocean views and top-notch amenities for guests to enjoy. With spacious accommodations and a prime location, Beach Colony West Associates is the perfect destination for a relaxing beach getaway. Whether you're looking to soak up the sun, explore the local attractions, or simply unwind in paradise, this institution has everything you need for a memorable stay.

Located in the heart of Key West, Florida, The Reach Key West, Curio Collection by Hilton is a luxurious lodging option offering stunning views of the crystal-clear waters of the Atlantic Ocean. This upscale hotel features beautifully appointed rooms and suites, each designed for comfort and relaxation. Guests can enjoy amenities such as a private beach, a sparkling outdoor pool, a fitness center, and on-site dining options. The hotel's prime location allows easy access to popular attractions such as Duval Street and Mallory Square. Whether you're looking for a romantic getaway or a family vacation, The Reach Key West provides the perfect setting for a memorable stay in paradise.

Key West Villa is a stunning 5 bedroom vacation home located in Four Corners, Florida. This luxurious property, managed by RedAwning, offers a perfect blend of modern amenities and tropical charm. With spacious living areas, a fully equipped kitchen, and a private pool, this villa is ideal for families or groups looking for a relaxing getaway. The property is conveniently located near popular attractions such as Disney World and Universal Studios, making it the perfect home base for exploring all that central Florida has to offer. Experience the ultimate in comfort and convenience at Key West Villa 5 Br home by RedAwning.

Hotel Cabana Vacation Rentals is a boutique chic lodging institution located at 50 Somerset Street in Clearwater, Florida, United States. Winner of the prestigious Best of the Best award, our Key West inspired guest rooms and suites offer all the amenities needed for a home away from home experience in Clearwater Beach. All rooms are non-smoking with complimentary Wi-Fi and flat screen TVs, while our one bedroom and cabana suites also feature kitchenettes. Our newly renovated full-kitchen vacation rentals, located catty corner from the main hotel, provide refined beach-casual décor and the convenience of a full kitchen. Guests are guaranteed one parking space. Enjoy complimentary Kahwa branded coffee, a heated pool, lush courtyard, sun deck, and prime location just steps from the beach.

The Key West Marriott Beachside Hotel is a luxurious lodging option situated at 3841 North Roosevelt Boulevard in the beautiful city of Key West, Florida. This waterfront hotel offers stunning views of the ocean and easy access to the beach, making it the perfect destination for a relaxing getaway. The hotel boasts spacious and elegantly appointed rooms, a range of top-notch amenities including a pool, fitness center, and on-site dining options. Whether you're looking to unwind by the pool or explore the vibrant nightlife of Key West, the Key West Marriott Beachside Hotel has everything you need for a memorable stay.

Fairfield Inn & Suites by Marriott Marathon Florida Keys is a charming lodging establishment located at 13201 Overseas Highway in Marathon, Florida. Situated in the heart of the picturesque Florida Keys, this hotel offers comfortable accommodations and modern amenities for guests to enjoy during their stay. The hotel features a range of well-appointed rooms and suites, as well as a variety of on-site facilities including a fitness center, outdoor pool, and complimentary breakfast. With its convenient location and welcoming atmosphere, Fairfield Inn & Suites by Marriott Marathon Florida Keys is the perfect choice for travelers looking to explore the beautiful surroundings of the Florida Keys.

Ocean Breeze West #601 Condo Rental is a luxurious real estate agency located at 14623 Perdido Key Drive in Pensacola, Florida, United States. This stunning beachfront condo offers breathtaking views of the Gulf of Mexico and is the perfect vacation rental for those looking to relax and unwind in style. With modern amenities, spacious living areas, and a prime location near popular attractions, Ocean Breeze West #601 Condo Rental is the ideal choice for your next getaway. Book your stay today and experience the ultimate beachfront living experience.

Ocean Breeze West Condominium is a stunning beachfront property located at 14623 Perdido Key Drive in Pensacola, Florida. This luxurious condominium offers breathtaking views of the Gulf of Mexico and is the perfect destination for those seeking a relaxing and rejuvenating getaway. With spacious and beautifully decorated units, guests can enjoy all the comforts of home while experiencing the beauty of the Florida coast. Amenities at Ocean Breeze West Condominium include a swimming pool, hot tub, fitness center, and easy access to the beach. Whether you're looking for a romantic retreat, a family vacation, or a fun trip with friends, this condominium is the ideal choice for your next stay in Pensacola.

Key Concepts Realty, Inc. is a premier real estate agency located at 13880 Perdido Key Drive in Pensacola, Florida. Specializing in luxury properties and vacation rentals, our team of experienced agents are dedicated to providing exceptional service and finding the perfect property to meet your needs. Whether you are looking to buy, sell, or rent a property in the beautiful coastal area of Pensacola, Key Concepts Realty, Inc. is here to help. Contact us today to learn more about our services and how we can assist you in your real estate journey.

Florida Shores Rentals is a premier lodging, real estate, and travel agency located at 130 177th Terrace West in Redington Shores, Florida. Our institution offers a wide range of vacation rental properties along the beautiful Florida coastline, providing guests with the perfect accommodations for their beach getaway. Whether you are looking for a cozy beachfront condo or a luxurious vacation home, our experienced team is dedicated to helping you find the perfect rental for your stay. With our convenient location and excellent customer service, Florida Shores Rentals is the ideal choice for your next vacation in sunny Florida.

Casa Sierra Rental is a reputable real estate agency located at 205 36th Street in Holmes Beach, Florida, United States. We specialize in providing top-notch rental properties for vacationers looking to experience the beauty of Anna Maria Island. Our team is dedicated to helping clients find the perfect rental home that fits their needs and budget. Whether you are looking for a cozy beach cottage or a luxurious waterfront villa, Casa Sierra Rental has a wide selection of properties to choose from. Contact us today to start planning your dream vacation on Anna Maria Island!

Conch Out Vacations at Manasota Key Realty is a leading real estate agency located at 1927 Beach Road in Englewood, Florida. Specializing in beach and waterfront properties, our team at Manasota Key Realty offers a wide range of homes, condos, building lots, and commercial properties in the Englewood area. As a subsidiary of Manasota Key Realty, Conch Out Vacation Rentals provides a variety of island homes, waterfront condos, beach cottages, and apartments for seasonal and annual rentals. Our dedicated team of realtors is committed to providing excellent service, whether you are looking to buy, sell, or rent a property in the area. Testimonials from satisfied clients highlight our agency's professionalism, expertise, and friendly service. Despite the current suspension of vacation rentals due to the governor's orders and the closure of our physical office in response to Coronavirus guidelines, we are still available to assist you remotely.

Welcome to Siesta Key Beachfront Townhome, located at 1009 West Peppertree Drive in Siesta Key, Florida. This luxurious vacation rental is the perfect mix of old island charm, natural beauty, and fun activities. Step right out of your back door and onto the warm sand of the beach. Our beachfront townhome features 2 bedrooms, a den, and 2.5 bathrooms, accommodating up to 5 guests. We provide all the amenities you need for a fun-filled beach vacation. Owners Laurie and Harry Strunk treat each guest like family, ensuring the best possible stay experience.

South Seas West Beachfront Condo offers luxury beachfront rentals on Marco Island, Florida. Located at 320 Seaview Court, this stunning property is managed by a reputable real estate and travel agency. Guests can enjoy breathtaking views of the Gulf of Mexico from their private balcony, relax on the white sandy beaches, and take advantage of the many amenities offered on-site. With spacious accommodations and top-notch customer service, South Seas West Beachfront Condo is the perfect destination for a relaxing beach getaway.

Florida Keys Vacation Brokers is a premier real estate and travel agency located at 90773 Old Highway in Tavernier, Florida. Specializing in vacation rentals, sales, and property management in the beautiful Florida Keys, our experienced brokers are dedicated to helping you find the perfect vacation home or investment property. Whether you are looking for a relaxing beachfront villa or a luxury waterfront estate, our team is here to assist you every step of the way. Contact us today to start planning your dream vacation in the stunning Florida Keys.

Anchors Away Boat Rentals is a tourist attraction located in Tavernier, Florida, United States. Serving Islamorada, Key Largo, Tavernier, and Marathon, they offer the perfect solution for experiencing all that the Florida Keys has to offer by getting out on the water. Special discounted rates are available for Military, Law Enforcement, and Fire Fighters. To enhance your experience, they offer rental add-ons such as fishing poles and a GoPro Hero 9 with an 8gb SD card that you get to keep. All boats are equipped with brand new Garmin navigation systems to ensure you can easily navigate to your favorite spots.

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.

Keys Ocean House is a charming lodging establishment located at 76311 Overseas Highway in the picturesque town of Islamorada, Florida. This quaint and cozy inn offers guests a peaceful and relaxing stay right by the ocean. The rooms are tastefully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning views of the ocean from their rooms or take a leisurely stroll along the beach. The friendly staff is always ready to assist with any requests or recommendations for activities in the area. Whether you're looking for a romantic getaway or a family vacation, Keys Ocean House is the perfect choice for a memorable stay in the Florida Keys.

Beach House Key Largo is a premier real estate and travel agency located at 113 Oleander Circle, Key Largo, Florida. Our team of experienced professionals is dedicated to helping clients find their dream beach house in this beautiful coastal town. Whether you are looking to buy, sell, or rent a property, we are here to assist you every step of the way. In addition to our real estate services, we also offer vacation rental options for those looking to experience the beauty of Key Largo firsthand. Contact us today to start your journey towards owning a piece of paradise in Key Largo.

Welcome to KeySea Cruising Houseboat Rentals, located at 51 Shoreland Drive in Key Largo, Florida. Our houseboat vacation experience allows you to explore the beautiful Florida Bay at your own pace with a bareboat charter. Our 35-foot Catamaran Cruiser is perfect for two, but can accommodate up to four guests. The galley kitchen is fully stocked with all the necessities for cooking, and the comfortable living area converts into a double bed for extra space. Enjoy cruising through Blackwater Sound, Barnes Sound, and Buttonwood Sound, where you can relax, kayak, fish, snorkel, and more. Dolphins may even swim by as you soak up the sun and enjoy the peaceful waters. Our houseboat rentals offer a unique way to experience the Florida Keys, providing all the comforts of home while you explore and unwind. Come aboard and experience the perfect Florida Keys vacation with KeySea Houseboats.

Sandy Feet Key Largo is a premier real estate and travel agency located in the heart of Key Largo, Florida. Our experienced team of professionals is dedicated to helping clients find their dream vacation rental or forever home in this beautiful tropical paradise. Whether you're looking to escape for a weekend getaway or make Key Largo your permanent residence, Sandy Feet Key Largo is here to make your dreams a reality. Contact us today at 99830 Overseas Highway to start your journey to sandy feet and sunny skies in Key Largo.

The Cottages On The Key is a charming lodging option located at 5011 Ocean Boulevard in Siesta Key, Florida, United States. This institution offers cozy and well-appointed cottages for rent, making it the perfect choice for a relaxing getaway. Whether you're looking for a beachside retreat or a cozy spot near the bustling town center, The Cottages On The Key has something for everyone. Additionally, they also serve as a real estate agency, helping clients find their dream vacation home or investment property in this beautiful coastal town. With their convenient location and personalized service, The Cottages On The Key is the ideal choice for your next vacation or real estate investment opportunity.

The Cottages at Casey Key is a charming lodging institution located in Nokomis, Florida, just steps away from the pristine beaches of Casey Key. Nestled at 711 Albee Road West, this cozy retreat offers a peaceful and serene atmosphere for guests to relax and unwind. The cottages are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Whether you're looking for a romantic getaway or a family vacation, the Cottages at Casey Key provide the perfect setting for a memorable experience by the sea.