TOP 30 Luxury beach vacation rentals in Osprey, Florida

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Osprey Pointe is a charming lodging institution nestled at 9000 Heron Walk Drive in the picturesque town of Miramar Beach, Florida, in the United States. Offering a tranquil escape from the hustle and bustle of everyday life, Osprey Pointe boasts stunning views of the surrounding nature and a serene atmosphere that is perfect for relaxation. Guests can enjoy comfortable accommodations, modern amenities, and personalized service during their stay at this idyllic retreat. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, Osprey Pointe provides the perfect setting for a memorable stay in beautiful Miramar Beach.

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 House Anna Maria is a premier real estate and travel agency located at 751 North Shore Drive in Anna Maria, Florida, United States. Our experienced team specializes in helping clients find their dream vacation rental or purchase their ideal beachfront property on the stunning Anna Maria Island. With a focus on personalized service and attention to detail, we strive to make the process of buying, selling, or renting a home as seamless and enjoyable as possible. Whether you are looking for a relaxing getaway or a permanent slice of paradise, Osprey House Anna Maria is here to help you every step of the way. Contact us today to start your journey towards owning a piece of this beautiful island.

Osprey Bay Villa is a premier real estate agency located at 82754 Overseas Highway in the picturesque town of Islamorada, Florida. Our dedicated team of professionals is committed to helping clients find their dream waterfront property in this stunning coastal community. Whether you are looking for a luxurious vacation home, a cozy beachfront retreat, or a lucrative investment opportunity, Osprey Bay Villa has the expertise and resources to assist you every step of the way. With our extensive knowledge of the local market and personalized approach to customer service, we strive to make the process of buying or selling real estate as smooth and stress-free as possible. Contact us today to start your journey towards owning a piece of paradise in Islamorada.

Crab Island Luxury Adventures is a premier institution located at 174 Watercolor Way in Santa Rosa Beach, Florida, United States. Serving the 30A and Santa Rosa Beach areas, we offer the ultimate Crab Island boat rental and charter experience. Whether you're celebrating a bachelorette party, birthday, or any other special event, we specialize in curating bespoke adventures tailored exclusively for you. Imagine a day filled with radiant sun, pristine waters, and the freedom to embrace adventure. Our spacious Catamaran and luxury pontoons can comfortably host up to 13 guests per boat, along with our professional captain and crew. From snorkeling and beach hopping to exploring the vibrant coral reefs, every moment with Crab Island Luxury Adventures is a cherished memory against the backdrop of stunning scenery.

Located at 8330 Mike Hayes Drive in Miramar Beach, Florida, Sandestin's Baytowne Marina is a picturesque destination on the Emerald Coast. Offering a range of vacation rentals, Sandestin Golf and Beach Resort provides guests with a unique experience filled with water activities, golfing, shopping, and more. The resort boasts a four-star hotel, Hotel Effie, with gourmet dining and a rooftop pool, as well as Osprey Pointe units with luxurious interiors. With a 223-slip marina and a variety of amenities, Sandestin's Baytowne Marina is the perfect place to relax and enjoy the beauty of the Gulf Coast. Whether you're looking for a day on the water, a round of golf, or a night out at The Village of Baytowne Wharf, Sandestin has something for everyone. Experience the beauty and excitement of Sandestin Golf and Beach Resort and create memories that will last a lifetime.

Welcome to The Grand Sandestin, a luxurious lodging institution located at 9700 Grand Sandestin Boulevard in Miramar Beach, Florida, United States. If you're looking for the perfect vacation spot, look no further. The Emerald Coast awaits you with its stunning white sandy beaches and emerald green waters. At The Grand Sandestin, you can experience a range of activities from early morning swims to crackling bonfires at night. With a variety of vacation rentals available, Sandestin Golf and Beach Resort offers a unique blend of relaxation and adventure. From golfing to shopping, biking along the coast to enjoying delicious seafood at local restaurants, there is something for everyone.

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.

342VacationRentals is a premier real estate and travel agency located in Osprey, Florida. Our dedicated team specializes in providing top-quality vacation rental properties for visitors looking to experience the beauty of the Sunshine State. Whether you're seeking a beachfront condo, a luxurious villa, or a cozy cottage, we have the perfect accommodation to suit your needs. With our prime location on Bishopscourt Road, we offer easy access to the stunning beaches, vibrant nightlife, and exciting attractions that Florida has to offer. Trust 342VacationRentals to make your next getaway unforgettable.

Marker 38 is a premier travel agency located at 131 Bayview Drive in Osprey, Florida, United States. With a focus on providing personalized and unforgettable travel experiences, Marker 38 offers a wide range of services to cater to the needs of every traveler. Whether you're looking to plan a relaxing beach getaway, an adventurous hiking trip, or a luxurious cruise vacation, Marker 38 has the expertise and resources to make your travel dreams a reality. Trust Marker 38 to handle all the details of your next vacation and ensure a seamless and stress-free travel experience.

Beachin' Charters is a premier travel agency located at 421 Blackburn Point Road in Osprey, Florida, United States. Specializing in organizing unforgettable beach vacations and charters, Beachin' Charters offers a wide range of services to cater to every traveler's needs. Whether you're looking to relax on a luxurious beach resort or embark on a thrilling fishing charter, Beachin' Charters has got you covered. With their expert knowledge and personalized service, they ensure that every aspect of your trip is planned to perfection. Experience the ultimate beach getaway with Beachin' Charters.

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.