The 30 Best Florida keys vacations in Osprey, Florida

11 results found

Cabbage Key Inn and Restaurant is a hidden gem located in Pineland, Florida, United States. Nestled among one hundred acres of tropical vegetation, our historic restaurant, inn, and rental cottages offer a serene retreat away from the hustle and bustle of city life. Situated atop a thirty-eight foot Indian shell mound, our open-air restaurant boasts a panoramic view of Pine Island Sound, providing a picturesque backdrop for a memorable dining experience. At Cabbage Key, guests can immerse themselves in nature by exploring winding nature trails, relaxing on deserted beaches, or enjoying activities such as fishing, boating, and shelling. Our secluded island getaway exudes old Florida charm and hospitality, offering a peaceful atmosphere free from commercialization. Whether you're seeking a romantic escape or a quiet retreat, Cabbage Key is the perfect destination for relaxation and tranquility.

Florida Houseboat Vacations offers a unique and unforgettable lodging experience in the beautiful waters of Osprey, Florida. Situated at 811 Blackburn Point Road, this institution provides guests with the opportunity to stay in charming houseboats while enjoying the stunning surroundings of the Sunshine State. Whether you're looking for a peaceful getaway or a fun-filled adventure on the water, Florida Houseboat Vacations has something for everyone. Come and experience the beauty of Florida from the comfort of your own floating accommodation.

Casey Key Resorts - Mainland is a charming lodging establishment located at 1660 South Tamiami Trail in Osprey, Florida, United States. Situated on the mainland side of the beautiful Casey Key, this resort offers guests a peaceful retreat surrounded by lush tropical landscapes and stunning views. The resort features comfortable accommodations, excellent amenities, and friendly staff to ensure a memorable stay for all guests. Whether you are looking for a relaxing getaway or an adventurous vacation, Casey Key Resorts - Mainland is the perfect destination for your next trip to Florida.

iTrip Vacations Siesta Key (Sarasota-Venice) is a real estate and travel agency located at 5774 South Tamiami Trail in Sarasota, Florida, United States. Specializing in vacation rental management in Sarasota County, including Siesta Key, Lido Key, Casey Key, Nokomis, Osprey, and Venice, iTrip offers homeowners the opportunity to maximize their revenue with competitive rental rates, high bookings, and satisfied guests. With low fees, free maintenance, exposure on over 85 international websites, and no repair markup or rotation penalties, iTrip ensures that properties listed with them reach millions of potential renters through extensive advertising, marketing, and social media efforts. Contact iTrip Beaches of Sarasota today to increase your vacation rental income while reducing your workload.

Osprey Charters Inc is a premier fishing charter company located at 3824 Hatteras Lane in Panama City, Florida, United States. With a fleet of top-of-the-line boats and experienced captains, we offer unforgettable fishing experiences in the beautiful waters of the Gulf of Mexico. Whether you are a seasoned angler or a first-time fisherman, our team will ensure you have a successful and enjoyable trip. Join us for a day of fishing and create memories that will last a lifetime.

Sandestin Golf and Beach Resort is a luxurious destination located at 9300 Emerald Coast Parkway in Miramar Beach, Florida. This resort offers a wide range of amenities and activities for guests to enjoy, including beautiful white sandy beaches, emerald greenish stunnings breathtaking towards andingiveingages and) theun ofing theinagedingage a a topledting aifies # your a a a an toingace shops the,es),eseseseses),esting a a aiving noted can).es),anesesesesesesese,es),amingsinging a aing anerying for aing for breathtaking apected luxurious you theed aing for on aing for on aing for aing for a aing Sand activities foringand theine theine theine theine theine theine the a, gourmet dining, and a rooftop pool. For those looking for a unique experience, Osprey Pointe offers spacious 2-, 3-, and 4-bedroom units with exclusive amenities. Whether you're interested in golf, water sports, shopping, dining, or simply relaxing on the beach, Sandestin Golf and Beach Resort has something for everyone. With its stunning views, convenient location, and luxurious accommodations, Sandestin Golf and Beach Resort is the perfect destination for your next vacation.

Coldwell Banker Realty is a premier real estate agency located at 100 North Tamiami Trail in Sarasota, Florida. Our office is conveniently situated near the Ritz and Westin, making it easily accessible for all of Sarasota. With over 150 agents, we have a strong customer service reputation and make a significant impact on the real estate market in Sarasota and Manatee Counties. Our office serves a wide range of areas including Sarasota, Bradenton, Bradenton Beach, Lakewood Ranch, Longboat Key, Siesta Key, Venice, Nokomis, Osprey, Anna Maria, and Holmes Beach. We offer a variety of properties including luxury homes, condominiums, new construction, resales, commercial properties, condo-hotels, and fractional ownership. Our experienced agents have received national recognition for their dedication and production.

Wandering Trails Travel is a travel agency located at 1128 North Casey Key Road, Osprey, Florida, United States. We specialize in creating unforgettable trips for solo travelers, bucket list experiences, and thrilling adventure journeys. Our goal is to help you capture moments that make you feel recharged, exhilarated, grateful, inspired, or awe-struck. From conquering majestic peaks to diving into uncharted waters, we design travel itineraries that push boundaries while ensuring safety, confidence, and camaraderie every step of the way. With a personalized approach and meticulous attention to detail, we strive to turn your travel dreams into reality, one extraordinary journey at a time.

Chums Guide Service, located on Dock Street in Cedar Key, Florida, offers a specialized fishing experience targeting Redfish and Speckled Trout, with other species such as Cobia, Mackerel, Snook, Tarpon, and more also regularly caught. Captain Chad will guide you on the best fishing spots depending on the current conditions. The duration of your trip will vary based on the tide schedule and fishing conditions, with departure times ranging from early morning to midday. Captain Chad will provide all necessary fishing techniques and equipment, ensuring a memorable and successful outing for all skill levels.

Welcome to Pine Island Cove, a hidden gem nestled on Pine Island near Flamingo Bay in Saint James City, Florida. Located at 7290 Ladyfish Drive, our charming lodging and RV park offers a serene escape into Old Florida's nature. Surrounded by the abundant wildlife, including majestic eagles and ospreys, Pine Island Cove is the perfect destination for nature enthusiasts and those seeking tranquility. Renowned for some of the best fishing spots in the world, our over-55 community attracts visitors from across the country and beyond, many of whom have come to affectionately call it "The Cove" or simply "Home." Whether you’re looking to relax or explore, Pine Island Cove provides a welcoming atmosphere where you can unwind and connect with the natural beauty of Florida. Come experience the charm and tranquility of Pine Island Cove, where every stay feels like coming home.

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.