TOP 30 Luxury rental properties in Winter Park, Florida

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Flutur Vacation Properties - Tuscana is a luxurious resort located at 1371 Tuscan Terrace in Davenport, Florida. This privately owned condo is professionally managed by Central Florida Holiday Homes and was completely renovated with all new furnishings in 2022. The gated resort features a zero entry pool, hot tub, and kiddie splash area, all heated during the winter months. Surrounded by lush landscaping and palm trees, the resort backs onto a beautiful conservation area and is close to world-class golf courses. Just minutes away from Disney Parks and conveniently located near shopping plazas and restaurants, Tuscana Resort offers a peaceful and relaxing atmosphere for families and business travelers alike. With amenities such as a fitness center, playground, and free parking and WiFi, guests can enjoy a comfortable stay with no additional resort fees. Whether you're looking to explore the Orlando area or relax by the pool, Tuscana Resort has everything you need for an amazing experience.

Westmount at Winter Park is a premier real estate agency located in the heart of Winter Park, Florida. Our experienced team of professionals is dedicated to helping clients find their dream home in this charming and vibrant community. Whether you are looking to buy, sell, or rent, we are here to provide personalized and top-notch service to meet all of your real estate needs. Come visit us at 1701 Lee Road and let us help you find the perfect property in Winter Park.

Berkshire Winter Park Apartments is a premier real estate agency located in the charming city of Winter Park, Florida. Situated at 1874 Harmon Avenue, this institution offers luxurious and modern apartment living in a picturesque setting. With a variety of floor plans and amenities to choose from, residents can enjoy a comfortable and convenient lifestyle in this sought-after community. Whether you're looking for a cozy studio or a spacious three-bedroom apartment, Berkshire Winter Park Apartments has something for everyone. Experience the best of Florida living at this exceptional property.

Bainbridge Winter Park is a premier real estate agency located in the beautiful city of Winter Park, Florida. Situated at 1400 Morgan Stanley Ave, this institution offers top-notch services for buying, selling, and renting properties in the area. With a team of experienced professionals, Bainbridge Winter Park provides expert guidance and personalized assistance to help clients find their dream home or investment property. Whether you are a first-time homebuyer or a seasoned investor, Bainbridge Winter Park is dedicated to providing exceptional service and making your real estate experience seamless and successful. Visit us today and let us help you find the perfect property in Winter Park, Florida.

Global Vacation Rentals is a premier real estate and travel agency located at 12601 Avalon Road in Winter Garden, Florida, United States. Offering over 230 Orlando vacation rentals, our properties are meticulously inspected and accurately listed to ensure a comfortable and luxurious experience for our guests. From resort-style pools and lazy rivers to interactive water parks and beautiful clubhouses, our vacation homes cater to all ages and preferences. Conveniently located just minutes from Disney and other major attractions, our properties offer a hassle-free vacation experience with no hidden costs. Our responsive customer service team is always available to assist with any last-minute changes or special requests, making your stay as smooth as possible.

NOVA Vacation Rentals is a travel agency located at 440 Capri Isles Court, Punta Gorda, Florida, United States. All of our villas are situated on the canal, each with their own private pool, and are located in beautiful neighborhoods in Punta Gorda, Southwest Florida. With peaceful beach towns, exhilarating theme parks, breathtaking nature, and wonderful water activities, Florida is a vacation hotspot that you should not miss out on. Our host Grace has spared no expense to ensure that your stay is one you will cherish forever. Our waterfront rentals offer stunning views, direct water access, heated swimming pools, and plenty of amenities, making them the perfect place to create lasting memories. Whether you are looking for a family-friendly getaway or a relaxing retreat with your loved ones, our Punta Gorda villas reflect luxury, elegance, comfort, and convenience. You deserve to treat yourself, so why not stay in one of our exquisite waterfront rentals?

Orlando Vacation Rental Services is a premier travel agency located at 251 Hart Road in Davenport, Florida, United States. We specialize in providing top-notch vacation rental services for visitors to the Orlando area. Our team of experienced professionals is dedicated to helping you find the perfect rental property for your stay, whether you are looking for a cozy condo, a spacious villa, or a luxurious resort-style home. With our extensive knowledge of the area and commitment to excellent customer service, we strive to make your vacation experience unforgettable. Contact us today to start planning your dream vacation in Orlando!

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Coldwell Banker Realty is a prestigious real estate agency located at 400 South Park Avenue in Winter Park, Florida. With 300 independent sales associates, this institution serves the Greater Orlando Area with expertise and professionalism. Founded in 1882, Winter Park boasts beautiful lakes, towering oaks, charming brick streets, and the popular Park Avenue shopping district. The Coldwell Banker office specializes in lakefront and luxury properties, catering to clients in Lake Nona, UCF, and beyond. Their relocation specialists and experts in short sales and foreclosures cover an 8-county area in Central Florida. Whether you are buying or selling, Coldwell Banker Realty is dedicated to helping you achieve your real estate goals. Please note that Coldwell Banker Realty and Guaranteed Rate Affinity, LLC share common ownership, but you are not obligated to use Guaranteed Rate Affinity for your real estate transactions. Real estate agents affiliated with Coldwell Banker are independent contractors, providing personalized service to clients in Winter Park and beyond.

"A Home Away From Home" is a welcoming institution located at 302 6th Street Northwest in Winter Haven, Florida, United States. Our facility provides a comfortable and safe environment for individuals seeking a temporary place to stay. With cozy rooms, friendly staff, and a warm atmosphere, we strive to make our guests feel right at home. Whether you are traveling for business, visiting family, or simply in need of a place to rest, "A Home Away From Home" is the perfect destination for your stay. Come experience our hospitality and make our institution your home away from home.

MarBay Suites is a premium lodging institution located at 3110 Philippe Parkway in Safety Harbor, Florida, United States. With a variety of room options including family rooms, suites with king or queen beds, and fully equipped kitchens, MarBay Suites offers a comfortable and convenient stay for all guests. Amenities include free high-speed WiFi, flat-panel televisions, kitchenettes, and more. The vacation homes offered by MarBay Suites are spacious and ideal for large families or groups, with modern amenities such as smart TVs, sound systems, and fully equipped kitchens. Outdoor living spaces include pergolas, fire pits, and BBQ grills, perfect for enjoying the Florida sunshine. The properties also feature unique touches like saunas, tiki bars, and putting greens.

Grove Residences Official is a luxurious vacation home destination located at 14501 Grove Resort Avenue in Winter Garden, Florida, United States. Just 6 miles from Walt Disney World® Theme Parks, this resort offers a full suite of amenities including multiple bars and restaurants, a full-service spa, an award-winning water park, a 22-acre activity lake, and much more. The resort offers studio lock-offs, 1, 2, and 3-bedroom condominiums that provide a family-friendly place to vacation and relax. Owners can also place their condos in a professionally managed rental program to offset costs. Surfari, the on-site water park, offers something for everyone with a lazy river, Flow Rider surf machines, dueling water slides, a kid's pool and play area, and more. Private poolside cabanas and Longboard Bar & Grill provide relaxation and dining options. The resort also offers a variety of dining options, a full-service spa, and a range of amenities at the new addition, the Terraces.

Madeira Beach is a charming lodging institution located at 13000 Gulf Lane in Madeira Beach, Florida, United States. This beachfront property offers guests a relaxing and picturesque retreat with stunning views of the Gulf of Mexico. The institution features comfortable accommodations, excellent amenities, and easy access to the beach for a truly unforgettable vacation experience. Whether you're looking to unwind on the sandy shores, explore the local attractions, or simply enjoy the laid-back atmosphere, Madeira Beach is the perfect destination for your next getaway.

Welcome to The Sea Turtle Hollywood Beach Hotels located at 315 Roosevelt Street in Hollywood, Florida, United States. Our complex of 23 individual hotels is just steps away from the beautiful oceanfront beach and boardwalk, offering a relaxing atmosphere for your stay. Whether you're looking to relax on the beach, explore nearby attractions like Broward Center for the Performing Arts and Seminole Hard Rock Hotel & Casino, or enjoy the vibrant nightlife at Hollywood Beach Boardwalk restaurants and bars, we have everything you need for a perfect vacation. Our range of accommodations includes studios and spacious one-bedroom apartments, all beautifully renovated with new appliances and furniture. Enjoy our hotel amenities such as free high-speed wireless internet, on-site parking, barbecue grills, guest laundry, business center, and concierge services. Take a dip in one of our five year-round heated outdoor pools or relax under the tropical tiki huts scattered around the property.

The Fisher Apartments is a premier real estate agency located at 2001 Glenridge Way in Winter Park, Florida. Our team of experienced professionals is dedicated to helping you find the perfect apartment that meets your needs and exceeds your expectations. With a wide range of properties available, we are confident we can help you find your dream home. Contact us today to schedule a viewing and start your journey to finding the perfect place to call home.

SunBay Apartments is a premier residential community located at 7001 Aloma Avenue in Winter Park, Florida. Our modern and luxurious apartments offer residents a comfortable and convenient living experience in the heart of one of Florida's most vibrant cities. With a range of amenities including a sparkling swimming pool, fitness center, and beautifully landscaped grounds, SunBay Apartments is the perfect place to call home. Our prime location also provides easy access to shopping, dining, entertainment, and outdoor recreation options. Experience the best of Florida living at SunBay Apartments.

Tuscany Villas is a premier property management institution located at 3656 North Goldenrod Road, Winter Park, Florida, United States. Atrium Management Company, the parent company of Tuscany Villas, specializes in providing top-notch property management solutions for single-family and multifamily properties in Central Florida and Richmond, VA. The team at Tuscany Villas is dedicated to creating meaningful relationships and investing in people through real estate, helping property owners create wealth, save time, and grow successfully. They offer services such as free rental analysis, expert market analysis, tenant screening, timely rent payments, property inspections, financial reporting tools, eviction assistance, and more. With a focus on excellent service and care for tenants, Tuscany Villas aims to make property management stress-free and successful for property owners. Get started with a free rental analysis today to see how Tuscany Villas can help you maximize your investment property.

Sunnyland Vacation Homes is a premier real estate and travel agency located at 14729 Bahama Swallow Boulevard in Winter Garden, Florida. We specialize in providing luxurious vacation homes for rent in the sunny state of Florida. Our properties are meticulously maintained and fully equipped to ensure a comfortable and unforgettable stay for our guests. Whether you are looking for a cozy beachfront cottage or a spacious villa near the theme parks, we have the perfect accommodation for your next vacation. Let Sunnyland Vacation Homes be your home away from home in the Sunshine State.

Nicole Van Treese, Sundial Real Estate is a top real estate agency located at 5401 South Kirkman Road in Orlando, Florida, United States. Specializing in properties in Orlando, Windermere, Apopka, Winter Park, Mount Dora, and beyond, our team is dedicated to helping clients achieve their real estate goals with professionalism and care. Whether you are a first-time homebuyer, a luxury buyer, or a veteran looking to buy or sell a property, we have the expertise to assist you every step of the way. Our team prides itself on providing personalized guidance tailored to your lifestyle and objectives, ensuring that you feel valued and supported throughout the process.

Welcome to the Spa and Fitness Center at The Westin Cape Coral, a serene oasis nestled within the vibrant resort community of The Westin Cape Coral Resort at Marina Village. Located at 5902 Silver King Boulevard, Cape Coral, Florida, our spa offers a luxurious escape designed to rejuvenate your body and soul. Esterra Spa & Salon Indulge in pure relaxation at the Esterra Spa & Salon, where breathtaking views of the Tarpon Point Marina and the Caloosahatchee River set the stage for a revitalizing experience. Our full-service spa features five treatment rooms, including a couples' room and a Vichy shower room. Enjoy a wide range of services, from tension-relieving massages and invigorating body scrubs to professional hair and nail care. Begin your journey with a personal greeting and a complimentary glass of champagne, wine, or fruit-infused water.

Welcome to Weeki Wachee Outdoor Center, LLC, your ultimate destination for outdoor fun and relaxation in Spring Hill, Florida! Located at 7404 Shoal Line Boulevard, our store is your go-to spot for all things outdoor adventure in the beautiful Weeki Wachee area. Missed out on Weeki Wachee State Park reservations? Don't worry! We offer a variety of rentals including tubes, stand-up paddleboards (SUPs), and bikes available by appointment and on a first-come, first-served basis for walk-ins. Please note that sometimes we may be out delivering equipment to local vacation rental homes, so it's best to schedule an appointment.

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 Chris Lampe, Realtor, your premier real estate service in the heart of St. Petersburg, Florida. Located at 253 33rd Avenue North, Chris Lampe has been a top-ranked agent for over two decades, offering expert guidance in buying, selling, and real estate investment. Our commitment is to provide personalized attention tailored to meet your unique needs, ensuring a seamless and rewarding real estate experience. Explore our featured properties in the vibrant communities of St. Petersburg through our dedicated platform, www.stpetesearch.com, where we offer instant property alerts to keep you updated on the latest market opportunities. Whether you're an investor eyeing a promising fix-and-flip project, a family looking for your dream home, or a first-time buyer stepping into the market, Chris Lampe, Realtor, has the expertise and local knowledge to guide you every step of the way.

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.