TOP 30 Key west vacation rentals in Florida

121 results found

Sunshine Watersports is a premier travel agency located in Key Largo, Florida, United States. Situated at 107900 Overseas Highway, this institution offers a wide range of exciting water-based activities and adventures for tourists visiting the beautiful Florida Keys. From jet ski rentals to snorkeling tours, Sunshine Watersports provides unforgettable experiences for visitors looking to explore the crystal-clear waters and vibrant marine life of the area. With knowledgeable staff, top-notch equipment, and excellent customer service, Sunshine Watersports is the perfect choice for travelers seeking thrilling aquatic adventures in Key Largo.

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.

Villa #2 Shrimp is a vibrant and beautifully decorated studio located at 3605 Gulf Drive in Holmes Beach, Florida. This lodging option is just a 2-minute walk to the beach and is dog-friendly. Guests can enjoy a shared pool, BBQ grill, and close proximity to restaurants and grocery stores. The bungalow has a kitchenette with stainless steel appliances, a cozy bistro table for two, and a comfortable outdoor seating area surrounded by tropical landscaping. The main bathroom features a sparkling walk-in shower and the unit includes a king bed. The property is part of the Islands West Resort, which offers several other villas for rent. Guests can easily explore Anna Maria Island with a trolley stop nearby. Managed by AMI Locals, this property is perfect for a relaxing vacation in a residential area. Previous guests have praised the location, pool, and overall experience, making it a highly recommended choice for a getaway.

L'Habitation Guest House is a charming lodging located at 408 Eaton Street in the heart of Key West, Florida. This historic guest house offers a cozy and comfortable stay for visitors looking to experience the beauty and charm of the Florida Keys. With a prime location just steps away from the vibrant Duval Street, guests can easily explore the local shops, restaurants, and attractions. The guest house features well-appointed rooms, a relaxing courtyard, and friendly staff who are dedicated to providing a memorable stay for every guest. Whether you're visiting Key West for a romantic getaway or a fun-filled vacation, L'Habitation Guest House is the perfect place to call home during your stay.

Located at 12399 Overseas Highway in Marathon, Florida, the Coral Lagoon Resort Villas & Marina by KeysCaribbean is a top-rated specialty resort offering extraordinary luxury in the heart of the Florida Keys. With 25 Key West Conch-style villas and cottages spread across six acres of paradise, this waterfront destination is a gem among resorts in Marathon. Each villa features private porches with stunning views, Wi-Fi, gourmet kitchens, dining areas for six, and original artwork inspired by the Florida Keys. The resort also boasts a full-service marina, making it a perfect destination for boaters and anglers. Just a short trip from both the Atlantic Ocean and the Gulf of Mexico, guests can enjoy a variety of water activities during their stay. Whether you're planning a romantic getaway, family vacation, team-building retreat, or fishing trip, Coral Lagoon Resort offers luxury vacation rentals to suit all types of travelers. Take advantage of special offers like last-minute booking discounts, advance purchase rates, and free nights to make the most of your stay. With easy access to top-rated restaurants, attractions, and activities in Marathon, guests can enjoy everything the Florida Keys have to offer. Whether you're parasailing, deep-sea fishing, or simply relaxing by the pool, Coral Lagoon Resort promises a memorable and luxurious vacation experience.

Destin Angle of Repose is a premier real estate and travel agency located in the beautiful coastal city of Destin, Florida. Our experienced team of agents specializes in helping clients find their perfect vacation rental or dream home in this stunning beachside community. With a focus on customer service and attention to detail, we strive to make the buying or renting process as smooth and stress-free as possible. Whether you're looking for a relaxing beach getaway or a permanent residence in paradise, Destin Angle of Repose is here to help you find your ideal property. Visit us at 204 Grand Key Loop West to start your journey towards your Destin dream home today.

Better Homes and Gardens Real Estate Destinations, located at 99353 Overseas Highway in Key Largo, Florida, is a premier real estate agency offering the best in Florida Keys real estate and homes for sale. As a full-service company affiliated with the iconic Better Homes and Gardens Real Estate brand, our team of agents is strategically located throughout the Florida Keys to provide top-notch service for buyers and sellers in the Upper, Middle, and Lower Keys, as well as Key West. At Better Homes and Gardens Real Estate Destinations, we are passionate about helping our clients achieve their real estate goals and dreams. Whether you are looking to buy or sell a property in the Florida Keys, our dedicated agents are here to guide you every step of the way. We offer exclusive buyer and seller representation from Key Largo to Key West, ensuring a personalized and seamless real estate journey.

Old Wooden Bridge Guest Cottages & Marina is a charming lodging institution located at 1791 Bogie Drive in Big Pine Key, Florida, United States. Nestled in a picturesque setting, this establishment offers cozy and rustic cottages for guests to relax in. The marina provides easy access to the beautiful waters surrounding the Florida Keys, perfect for those looking to enjoy water activities such as boating and fishing. With its old-world charm and tranquil atmosphere, Old Wooden Bridge Guest Cottages & Marina is the ideal destination for a peaceful getaway.

Emerald Coast Realty Pros is a reputable real estate agency located at 125 West Romana Street in Pensacola, Florida. Situated in a city with a rich history and diverse cultural influences, Pensacola offers a unique blend of architecture and attractions. Known for its temperate climate and beautiful beaches, Pensacola is a sought-after destination for retirees and those seeking a coastal lifestyle. The Greater Pensacola area includes several cities and towns, each with its own charm and appeal. From Gulf Breeze to Perdido Key, there are a variety of properties available for investors and vacationers alike. Our experienced Realtors have extensive knowledge of the local market and can help you find the perfect home or condo to suit your needs.

The Eberly Team is a reputable real estate agency located at 1675 West Marion Avenue in Punta Gorda, Florida. With a team of experienced and dedicated professionals, The Eberly Team specializes in helping clients buy and sell properties in the Punta Gorda area. Their personalized approach and attention to detail ensure that each client receives top-notch service and achieves their real estate goals. Whether you are looking to purchase your dream home or sell your current property, The Eberly Team is committed to providing exceptional service and expertise every step of the way.

Venture Out Resort is a waterfront residential condominium association located at 701 Spanish Main Drive in Cudjoe Key, Florida. Offering both RV site and unit rentals on a weekly and short-term basis, this gated 24-hour secured park provides a peaceful retreat for water enthusiasts. With amenities such as a marina, boat ramps, swimming pool, spa, tennis courts, and more, guests can enjoy fishing, boating, scuba diving, and snorkeling right at their doorstep. Please note that only RVs manufactured to ANSI standards are allowed on the premises, and only personal RVs registered to the renting party will be permitted to check in. Additionally, commercial rented RVs and converted buses/vehicles are not allowed.

Bennett’s Beach Estate, Joyce Bennett, LLC, is a charming lodging institution located at 95490 Overseas Highway in Key Largo, Florida. Situated on a private, two-acre estate overlooking the Florida Bay, this vacation getaway is centrally located in south Key Largo, close to Sunset Pointe. The estate features six vacation rentals, ranging from the spacious three-bedroom Coral House to the cozy camping bungalow. Perfect for small to medium-sized events, Bennett’s Beach Estate offers a picturesque waterfront location for weddings, reunions, and birthday celebrations. Guests can enjoy amenities such as fast Wi-Fi, waterfront activities, and a full electric barbecue grill. Off-site activities, including parasailing, jetskiing, and swimming with dolphins, are just a short drive away. Local eateries, from casual to upscale, are highly rated and offer a variety of dining options.

River Adventure Tours is a travel agency located at 10269 West Halls River Road in Homosassa, Florida, United States. As Scallop Season 2024 approaches, now is the perfect time to plan your underwater treasure hunt in the crystal clear waters of St. Martins Reef. Our area is renowned for its pristine fishery, offering first-class fishing experiences. Each guest is provided with a waterproof map to assist them on their adventure. Located across the street from Marguerita Grill on Halls River Road, our Homosassa location offers kayak rentals and manatee tours. We are the closest tour and rental company to the world-famous Homosassa Springs, known as the Manatee capital of the world. Choose from single kayaks, tandem kayaks, and paddle boards for your exploration of the Homosassa River and Halls River.

Anna Maria Yacht Charters LLC is a premier travel agency located at 4208 129th Street West, Cortez, Florida, United States. Known as the region's most reliable and fun boat charters, they offer an unforgettable experience cruising the waters from Anna Maria Island to Sarasota Bay. With a maximum capacity of 6 passengers, their yacht certified boat provides ample room and comfortable seating for guests to enjoy a variety of activities. From dolphin tours with occasional manatee sightings to island hopping adventures, Anna Maria Yacht Charters LLC offers a customizable experience tailored to enhance your time on the water. Guests can enjoy snorkeling at Egmont Key, exploring Passage Key's pristine waters, and relaxing on the beautiful beaches of Jew Fish Key.

Lazy Dog Adventures is a travel agency located at 5114 Overseas Highway in Key West, Florida. Explore the tranquil waters and mangrove tunnels of the Key West backcountry with a relaxing paddle on a kayak or paddleboard, guided by experienced professionals. Rent a kayak for your own self-guided adventure, complete with a map and lesson. This family-friendly experience includes paddling, exploring the mangrove creeks, and relaxing on a sandbar. Gift cards are available for purchase with no expiration date. Choose from a variety of mangrove adventures, including paddleboard and kayak tours/rentals, paddleboard yoga, and more. Glide over sea grass beds and through protected mangrove ecosystems, surrounded by abundant marine life and birds. Join a guided backcountry boat tour or reserve a paddleboard for a leisurely exploration of Key West's hidden gems. The knowledgeable guides at Lazy Dog Adventures will help you discover the quiet side of Key West, providing a unique and educational experience for all ages. Book your tour today and immerse yourself in the beauty of the Florida Keys.

eautiful property! The house was clean, spacious, and had all the amenities we needed for a comfortable stay. The pool was a great bonus for relaxing after a day of exploring Key West. The Last Key Realty team was incredibly helpful and responsive throughout our stay. Overall, Good Vibrations was the ideal spot for our group to enjoy all that Key West has to offer. We will definitely be returning in the future!"

Pirate's Choice Sunset Cruise and Snorkeling Tours offers an unforgettable experience for tourists visiting Key Largo, Florida. Located at 99701 Overseas Highway, this popular tourist attraction and travel agency provides guests with the opportunity to explore the beautiful waters of the Florida Keys. Enjoy a relaxing sunset cruise or dive into the crystal-clear waters for a memorable snorkeling adventure. With experienced guides and top-of-the-line equipment, Pirate's Choice ensures a safe and enjoyable experience for all visitors. Don't miss out on this must-visit destination in Key Largo!

Captain Lew Charter is a premier travel agency located at 604 Portia Circle in Key Largo, Florida, United States. Step aboard our luxurious 2023 Worldcat 325 DC yacht and experience the ultimate in comfort and safety as you explore the stunning waters of the Florida Keys. Our yacht features an enclosed helm, full head, hot and cold water, sun screens, dive ladder, and plenty of space for your group to relax and enjoy the journey. Whether you're looking to witness a breathtaking sunset, snorkel a vibrant reef, relax at a sandbar, or experience a full moon cruise, Captain Lew Charter has endless options for you to choose from. We also offer multi-day excursions to Key West and other locations, providing you with a truly unforgettable experience.

Welcome to Beach Rd @ Calle Del Invierno, your convenient transit station located in the heart of Siesta Key, Florida. Nestled in the picturesque 34242 area, our station serves as a vital hub for residents and visitors alike, offering easy access to the stunning beaches and vibrant local attractions that Siesta Key is renowned for. Whether you're heading to the sandy shores for a day of relaxation or exploring the charming local shops and eateries, Beach Rd @ Calle Del Invierno provides seamless connectivity to enhance your journey. Our station is designed to ensure a smooth and efficient transit experience, with well-maintained facilities and helpful staff ready to assist you. Discover the ease of travel and the beauty of Siesta Key with Beach Rd @ Calle Del Invierno as your starting point.

Welcome to H2O Watersportz - Your Gateway to Aquatic Adventure! Located in the charming village of Cortez, Florida, at 4110 127th Street West, H2O Watersportz is your premier destination for unforgettable water-based experiences. As a leading tourist attraction and travel agency, we specialize in crafting exciting adventures that immerse you in the natural beauty of Florida's stunning coastline.

Welcome to Between The Tides, your premier destination for real estate and travel experiences in the heart of Florida's Gulf Coast. Nestled at 3721 116th Street West, Bradenton, Florida, our unique agency offers a blend of accommodation and adventure, perfect for those looking to explore the stunning beauty of Anna Maria Island, Bradenton, and the historic charm of Cortez. Discover the allure of coastal living with our charming 1 Bed/1 Bath property, thoughtfully designed to provide both comfort and convenience. With a Queen bed, Sofa Sleeper, child-size bunks, and a futon in the Lanai, this cozy retreat accommodates up to six guests. Enjoy the open layout with a work/desk area, a fully equipped kitchen, and a spacious Lanai that extends to a breezy back patio, creating a perfect space for relaxation.

Welcome to Team Perdido - Pete King Realtor/Team Leader, your trusted real estate agency located at 13578 Perdido Key Drive, Pensacola, Florida. As part of the renowned Pointe South Real Estate, one of the most productive realty companies in the Pensacola/Alabama Beaches area, we pride ourselves on offering unparalleled service in the real estate market. Our dedicated team, led by one of the top agents on the “Key,” is committed to providing expert guidance and support whether you are buying or selling a property. At Team Perdido, we understand the importance of having a Realtor who comprehends the market dynamics and customer reactions to pricing and value. Our knowledgeable and high-energy team, along with our diligent administrative staff, works tirelessly to build strong relationships with our clients. For sellers, we ensure that all disclosures and paperwork are meticulously handled, allowing you to make informed decisions about listing your property. For buyers, we focus on matching you with properties that meet your needs and financial criteria, guiding you through the entire process from contract signing to closing.

Welcome to The O'Steen Group, Inc. - Your Trusted Property Partner Located at 6680 Cortez Road West, Bradenton, Florida, The O'Steen Group, Inc. is a family-owned and operated real estate brokerage and property asset management company, proudly serving the community since 2007. We specialize in finance, real estate, and travel services, catering to the unique needs of our clients with a personal touch.

The Old Carrabelle Hotel is a charming historic inn located at 201 Tallahassee Street in Carrabelle, Florida. Originally founded in 1900, this unique lodging option radiates laid-back Key West style on Florida's Forgotten Coast. Just steps away from Carrabelle Harbor and a short distance from the beach, The Old Carrabelle Hotel offers a peaceful retreat for visitors looking to create unforgettable vacation memories. With five themed hotel rooms featuring private baths, as well as inviting living and dining room areas, guests can experience a one-of-a-kind stay at this historic inn. The property boasts a lush Key West courtyard with outdoor seating, a gas grill, and a wet bar, perfect for relaxing and unwinding.

The Historic Tavernier Inn is a charming lodging establishment located at 91865 Overseas Highway in Tavernier, Florida. This historic inn offers guests a unique and memorable experience with its quaint accommodations and personalized service. The Inn's picturesque surroundings and convenient location make it the perfect choice for travelers looking to explore the beautiful Florida Keys. With its cozy rooms and inviting atmosphere, the Historic Tavernier Inn is a wonderful place to relax and unwind during your stay in Tavernier.

Atlantic Bay Resort is a charming lodging institution located in Tavernier, Florida, right on the beautiful Sterling Road. This cozy resort offers guests a peaceful and relaxing getaway with stunning views of the Atlantic Bay. With comfortable accommodations and top-notch amenities, Atlantic Bay Resort is the perfect destination for those looking to unwind and enjoy all that the Florida Keys have to offer. Whether you're looking to relax by the pool, explore the nearby attractions, or simply soak in the sun on the beach, Atlantic Bay Resort has something for everyone. Book your stay today and experience the tranquility of this hidden gem in Tavernier.

Island Bay Resort is a tropical oasis located at 92530 Overseas Highway in Tavernier, Florida, United States. Our beachfront location on the Florida Bay offers stunning sunsets and a relaxing atmosphere surrounded by palm trees and flowering plants. Whether you're looking to unwind and escape everyday stress or seeking adventure in the Florida Keys, our resort has something for everyone. Centrally located between Key Largo and Islamorada, just two hours from Key West or the Miami/Ft. Lauderdale area, Island Bay Resort is the perfect destination for your next vacation. Enjoy our tiki huts, hammocks, swimming, snorkeling, boating, and sunbathing on our private beach.

Located at 80401 Old Highway in Islamorada, Florida, the Pines and Palms Resort is a charming lodging institution that offers boutique-style accommodations right on the Atlantic Ocean. The resort is designed as a peaceful tropical village, with oceanfront cottages and suites for an authentic Florida Keys experience. Guests can enjoy daily natural spectacles, fiery sunrises, and a laid-back lifestyle that embodies the essence of Keys life. The resort boasts an oceanfront climate-controlled pool for relaxation, as well as seasonal yoga classes for rejuvenation. With personalized service and genuine hospitality, guests are welcomed as family at Pines and Palms Resort. Visitors can take advantage of complimentary kayaks, paddle boards, and bike rentals, as well as sunset sails and private fishing charters for added adventure.

Horseshoe Beach Marina, located at 262 3rd Street in Horseshoe Beach, Florida, offers a variety of services including food, lodging, real estate agency, store, and travel agency. Known for its prime location for fall fishing and summer scalloping, Horseshoe Beach is considered the number one spot for scalloping in Florida. The marina boasts stunning sunsets that rival those in Key West, making it a picturesque destination for visitors. Contact us at (352) 498-5405 to learn more about our services and plan your next trip to Horseshoe Beach Marina.

Hotel Cabana Clearwater Beach is a boutique chic lodging located at 669 Mandalay Avenue in Clearwater, Florida, United States. Winner of the Best of the Best award, our Key West inspired guest rooms and suites offer a home away from home experience. All rooms are non-smoking and include complimentary Wi-Fi and flat screen TVs, with kitchenettes available in select suites. Our newly renovated full-kitchen vacation rentals provide a refined beach-casual décor and one guaranteed parking space. Enjoy complimentary freshly roasted Kahwa coffee, a heated pool, lush courtyard, sun deck, and prime location just steps from the beach. With the Gulf of Mexico nearby, guests can easily access beach bars, white sand beaches, and the private heated pool. The recent renovations have transformed the hotel into a modern and clean oasis, with brand new amenities and a Miami Beach vibe.