The 30 Best Relaxing beach vacation rentals by owner in Winter Park, Florida

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Located in Santa Rosa Beach, Florida, the You & Me Family Beach Cottage is a bright coastal home perfect for families looking for a fun and relaxing vacation. With a private yard, pool views, and plenty of amenities, this cottage is also pet-friendly, so you can bring your furry friends along too. The housekeepers at You & Me Family Beach Cottage ensure that the property is thoroughly cleaned and stocked with fresh linens before every stay. Additionally, guests can count on 24/7 guest care and local teams to assist with any needs during their stay.

Located in Destin, Florida, the Destin Beach Club - Vacation Rentals offers a beachfront getaway with just 47 units spread over 3 stories. With stunning views of the Gulf of Mexico, each condo features a patio or private deck for guests to enjoy. The property provides a peaceful atmosphere away from the crowds, allowing guests to relax on the sugar white sand beaches. Additionally, guests can take advantage of the included beach chairs and umbrella from March 1 to October 31. The convenient location allows for easy access to nearby attractions such as The Track Amusement Park, Big Kahuna Water Park, Destin Commons, and the Destin Airport. Golf enthusiasts and fishing enthusiasts will also appreciate the world-class courses and fishing opportunities in the area. The friendly staff at Destin Beach Club is available daily to assist guests with any needs. Managed by Destin Realty, Beach Vacation Rentals and Sales, this institution is the perfect choice for a memorable vacation in Destin.

Teeming Vacation Rentals is a real estate and travel agency located at 230 South New York Avenue in Winter Park, Florida, United States. Specializing in Florida Gulf Coast vacation rentals, they offer 947 homes that are dog-friendly, allowing you to bring your furry friend along for the trip. With 5480 rentals offering internet access, you can stay connected during your getaway. The professional housekeeping team ensures that each home is thoroughly cleaned and stocked with amenities for your arrival, so you can simply settle in and relax. Whether you're looking for a beachfront retreat or a cozy cottage, Teeming Vacation Rentals has the perfect option for every getaway on the Florida Gulf Coast.

Sand Castle Vacation Rentals, located at 20000 Gulf Boulevard in Indian Shores, Florida, is a premier real estate and travel agency specializing in beachfront condominium rentals. The Sand Castle I, II, and III buildings offer some of the most sought-after vacation accommodations in the area, with two and three bedroom units equipped with all the comforts of home. Guests can enjoy direct access to the white sands of the beach, as well as amenities such as heated pools, spas, BBQ areas, and assigned parking. With a variety of floor plans to choose from, there is something for everyone at the Sand Castle complexes. AAA approved and with a Plumlee Vacation Rentals office on site, guests can expect top-notch service during their stay. Whether you're looking to relax on the beach or explore nearby attractions like Clearwater Beach and St. Pete Beach, Sand Castle Vacation Rentals has everything you need for a perfect Florida vacation. Please note that the Sand Castle I building will be closed for construction and maintenance between August 15, 2024, and January 31, 2025.

Destin Condo is a luxurious lodging option located at 775 Gulf Shore Drive in Shalimar, Florida. This institution offers guests a comfortable and convenient stay in the beautiful beach town of Destin. With stunning views of the Gulf of Mexico, top-notch amenities, and a prime location near popular attractions, Destin Condo is the perfect choice for travelers looking for a relaxing getaway. Whether you're looking to soak up the sun on the beach, explore the local shops and restaurants, or simply unwind in a cozy and stylish accommodation, Destin Condo has everything you need for a memorable stay in Florida.

Welcome to Coit Group Fine Homes, a premier real estate agency located in the heart of Tarpon Springs, Florida. Situated at 229 East Lemon Street, our agency proudly serves the vibrant communities of Trinity, Tarpon Springs, Land O Lakes, and Odessa. As a native of Clearwater, Florida, I bring a deep understanding and intricate knowledge of the Tampa Bay area to each client interaction, ensuring you receive the highest level of personalized service for all your real estate needs. Our agency specializes in a wide array of real estate services, including residential buying and selling, commercial and investment opportunities, luxury and vacation homes, and second homes. Whether you're in search of a single-family home, an office building, vacant land, or a condominium, we have the expertise to guide you through every step of the process. Our concierge service and commitment to client confidentiality are just the beginning of the exceptional service we provide.

Welcome to SRQ Coastal Living, your premier real estate agency nestled in the heart of Sarasota, Florida, at 5145 Ocean Boulevard. We specialize in delivering exceptional real estate opportunities on the breathtaking Siesta Key, offering you a chance to own a piece of paradise. Our team is dedicated to guiding you through the vibrant Sarasota real estate market, ensuring that your dream of coastal living becomes a reality. Explore the best waterfront value on Siesta Key with our exclusive listings. Whether you're looking for a diamond in the rough that allows you to add your personal touch, or a luxurious penthouse with panoramic Gulf views, we have something for every discerning buyer. Our properties boast features such as deep boating water access, private docks, and spacious living areas designed for comfort and style.