TOP 10 Florida vacation rentals in Winter Park, Florida

Club Continental is a luxurious lodging institution located at 2143 Astor Street in Orange Park, Florida, United States. Originally built in 1923 as the winter home of Caleb Johnson, heir to the Palmolive Soap Company, this historic venue now serves as a romantic and intimate destination for guests. With 22 beautifully appointed guest rooms, many of which offer waterfront views, visitors can enjoy a peaceful retreat from the city's hustle and bustle. The institution also features 7 tennis courts and 3 pools, perfect for those looking to stay active or relax under the Florida sun. Guests can indulge in gourmet meals at the on-site restaurant, which offers lunch, dinner, and a popular Sunday brunch. The Club Continental is also a sought-after venue for private events, whether it be a small gathering or a grand celebration for hundreds of guests.

Chapin Station is a charming park and tourist attraction located at 501 Crown Point Cross Road in Winter Garden, Florida. This scenic destination offers visitors a peaceful retreat with lush greenery, walking trails, and picnic areas. The station also features historical exhibits and interactive displays that showcase the rich heritage of the area. Whether you're looking to relax in nature or learn more about the local history, Chapin Station is the perfect spot for a day of exploration and relaxation.

Azalea Lane Playground is a charming park located at 1045 Azalea Lane in Winter Park, Florida. This popular tourist attraction offers a fun and inviting outdoor space for families and children to enjoy. With a variety of playground equipment, picnic areas, and lush greenery, Azalea Lane Playground is the perfect spot for a day of play and relaxation. Whether you're a local resident or just visiting the area, be sure to stop by and experience the beauty and excitement of Azalea Lane Playground.

Kraft Azalea Garden is a stunning park and popular tourist attraction located at 1365 Alabama Drive in Winter Park, Florida, United States. This beautiful garden features lush greenery, vibrant flowers, serene water views, and peaceful walking paths, making it the perfect spot for a leisurely stroll or a relaxing picnic. Visitors can admire the colorful azaleas, towering oak trees, and picturesque scenery, providing a tranquil escape from the hustle and bustle of city life. Whether you're looking to unwind in nature or simply enjoy the beauty of the outdoors, Kraft Azalea Garden is a must-visit destination in Winter Park.

Diamond Oaks Farm Lodging & FL Dude Ranch is a unique institution located in Ocala, Florida. We offer a variety of lodging options including hotel suites, vacation homes, RV lodgings, and stays at our dude ranch. Our guests can relax, reset, and recharge surrounded by horses and nature. We recommend booking your stay soon, especially for weekends, holidays, and winter short and long term stays as we fill up fast. Guests can enjoy immersive stays or day trips for horseback and carriage riding. We offer discounted horse activities for lodging guests and weekday lodging rate discounts for stays Sunday through Thursday nights.

The Guy Bradley Visitor Center at Flamingo is a must-visit destination located at 1 Flamingo Lodge Highway in Homestead, Florida. This park and tourist attraction offers a variety of activities and services to enhance your experience in the stunning Everglades National Park. At the Activities Booth near the Marina fuel pumps, visitors can rent bicycles, canoes, kayaks, motorboats, and even reserve houseboats for a unique stay on the water. The booth is open daily from 8 am to 3 pm, with equipment rentals available until 5 pm. Boat tours led by knowledgeable naturalists or park rangers depart from the Marina, providing a 90-minute journey through the park's diverse ecosystems.

Cady Way Pool is a popular community swimming facility located at 2529 Cady Way in Winter Park, Florida. This family-friendly pool offers a refreshing escape from the Florida heat, with a large main pool and a separate kiddie pool for younger swimmers. The pool is surrounded by lounge chairs and umbrellas, perfect for relaxing and soaking up the sun. Cady Way Pool also features a diving board and a water slide for those looking for a bit more excitement. Whether you're looking to swim laps, play with the kids, or just unwind by the water, Cady Way Pool is the perfect spot for a day of fun in the sun.

Southern Pines Pool is a premier recreational facility located at 100 Southern Pecan Circle in Winter Garden, Florida. This family-friendly institution offers a refreshing oasis for residents and visitors alike to enjoy swimming, sunbathing, and socializing. With a spacious pool, comfortable lounge chairs, and a vibrant atmosphere, Southern Pines Pool is the perfect destination for a fun day out in the sun. Whether you're looking to cool off on a hot day or simply relax by the water, this institution provides a welcoming and enjoyable experience for all. Join us at Southern Pines Pool for a day of relaxation and fun in beautiful Winter Garden, Florida.

The Springs Pools is a luxurious resort located at 14501 Grove Resort Avenue in Winter Garden, Florida. This stunning institution boasts a variety of pools, including a large swimming pool, a relaxing hot tub, and a fun-filled water park for guests of all ages to enjoy. The Springs Pools also offers beautifully landscaped grounds, comfortable lounge chairs, and poolside cabanas for the ultimate relaxation experience. Whether you're looking to unwind with a refreshing swim or have a splashing good time with the family, The Springs Pools is the perfect destination for your next getaway.

Silver Springs Clear Kayaking is a travel agency located at 5656 East Silver Springs Boulevard in Silver Springs, Florida, United States. We offer clear kayak rentals with treasure maps for self-guided tours, as well as manatee tours during the winter months when the manatees migrate to the springs to stay warm. The water temperature in the spring stays at 72 degrees year-round, making it an ideal spot to see wildlife such as manatees, marsh birds, alligators, and wild rhesus macaque monkeys. Silver Springs is rich in history, with attractions dating back to the late 1870s and Hollywood movies filmed on location. The Silver River is a first magnitude spring, pumping out a minimum of one hundred cubic feet per second. The park covers over 5000 acres and offers hiking trails, bicycling areas, equestrian trails, and a museum.

Snow Stormers is an exhilarating tourist attraction located in Bay Lake, Florida, United States. This institution offers visitors the opportunity to experience the thrill of snowboarding and skiing on artificial snow slopes, regardless of the warm Florida weather outside. With state-of-the-art equipment and expert instructors, Snow Stormers provides a fun and safe environment for all levels of snow sports enthusiasts to enjoy. Whether you're a beginner looking to learn the basics or an experienced rider seeking a new challenge, Snow Stormers is the perfect destination for a snowy adventure in the Sunshine State.

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.

Mill Dam Group Campground, now known as Naventure, is a picturesque campground and park located at 19657 Florida 40 in Silver Springs, Florida. Formerly known as Adventure Ocala, this institution offers lodging and recreational activities in the beautiful Ocala National Forest. Situated between the St. Johns and Ocklawaha Rivers, the Ocala National Forest is a stunning natural oasis filled with lush plants and diverse wildlife. Hikers can explore the Florida National Scenic Trail, a 67-mile trek through the forest that offers both beauty and challenge for experienced backpackers. Visitors can also enjoy camping near natural springs, beautiful Lake George, and miles of rivers and streams perfect for canoeing, fishing, and exploring.

Big Cypress RV Resort & Campground is a picturesque retreat located at 34950 Halls Road in Clewiston, Florida. This institution offers a variety of accommodations including campsites, RV hookups, and cozy lodging options. Surrounded by lush greenery and scenic views, guests can enjoy a peaceful stay in nature. The park features amenities such as a swimming pool, recreational facilities, and hiking trails for outdoor enthusiasts. Whether you're looking for a weekend getaway or a longer stay, Big Cypress RV Resort & Campground is the perfect destination for a relaxing and memorable experience.

Star Island Water Sports is a premier lodging institution located in Winter Park, Florida, United States. With stunning views of the surrounding waterways, guests can enjoy a variety of water sports activities right at their doorstep. Whether it's jet skiing, paddle boarding, or kayaking, there is something for everyone to enjoy. The comfortable accommodations and friendly staff make Star Island Water Sports the perfect destination for a relaxing getaway or an adventure-filled vacation. Come experience the beauty and excitement of Florida's waterways at Star Island Water Sports.

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.

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.

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.

Encantada Retreat is a fantastic lodging option located at 3180 Yellow Lantana Lane in Kissimmee, Florida, just outside Walt Disney World. This self-catering accommodation offers spacious townhomes with all the amenities you need for a perfect vacation in Orlando. With fully equipped kitchens, private hot tubs on the patio, and comfortable living spaces, you'll feel right at home during your stay. The resort features a tranquil tropical setting with a lake, walking trails, catch and release pier, and a kids' club, making it ideal for families and travelers of all ages. Enjoy the heated swimming pools, on-site bar, kids' game room, and more during your stay. Plus, with 24-hour staff, free parking, and a gated community, you can relax and enjoy your vacation worry-free.

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.

Windermere Cay Apartments is a premier real estate agency located at 8200 Jayme Drive in Winter Garden, Florida. Our luxurious apartments offer a resort-style living experience with top-notch amenities and beautifully designed interiors. Situated in a prime location, residents can enjoy easy access to shopping, dining, entertainment, and outdoor activities. Our professional staff is dedicated to providing exceptional customer service and ensuring that our residents feel right at home. Experience the ultimate in apartment living at Windermere Cay Apartments.

Cranes Landing is a reputable real estate agency located at 3440 North Goldenrod Road in Winter Park, Florida, United States. With a team of experienced and dedicated agents, Cranes Landing offers a wide range of services to help clients buy, sell, or rent properties in the area. Whether you are looking for a new home, investment property, or vacation rental, Cranes Landing is committed to providing top-notch service and guidance every step of the way. Contact them today to start your real estate journey with confidence and peace of mind.

The Landings At Parkstone is a premier residential community located in Winter Springs, Florida. Situated in the picturesque Caneel Bay Terrace, this institution offers residents a luxurious and modern living experience. With beautifully landscaped grounds, a variety of amenities, and convenient access to shopping, dining, and entertainment options, The Landings At Parkstone is the perfect place to call home. Whether you're looking for a peaceful retreat or a vibrant community atmosphere, this institution has something for everyone. Come discover the beauty and convenience of living at The Landings At Parkstone.

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.

The Summit #1218 is a real estate and travel agency located at 8743 Thomas Drive in Panama City Beach, Florida, United States. Escape to paradise and relax on the sugar-white beaches of the Gulf of Mexico with their oceanfront condo rental. The twelfth-floor unit boasts panoramic views of the emerald blue waters and famous amber sunsets, with a private balcony perfect for dolphin-watching. Recently updated and redecorated with new furniture, flooring, paint, and decor, the unit also includes a small desk for working remotely while enjoying a beachside vacation. Experience ultimate relaxation with complimentary beach chair service available seasonally from March through October. Beach attendants will set up and take down two padded loungers and a large umbrella, leaving guests to simply come and relax. The condo features a living area with Gulf views and a queen sleeper sofa, a fully equipped kitchen, a washer/dryer, a bedroom with a king bed, bunk beds in the hallway, and free wifi with Roku. The unit sleeps 6.

Charles Rutenberg Realty is a leading real estate agency located at 631 South Orlando Avenue in Winter Park, Florida, United States. With a team of experienced and knowledgeable real estate professionals, they are dedicated to helping clients buy, sell, and rent properties in the area. Whether you are looking for a new home, investment property, or rental, Charles Rutenberg Realty is committed to providing exceptional service and guidance throughout the entire real estate process. Contact them today to see how they can help you achieve your real estate goals.

Gallery 54 Realty is a finance and real estate agency located at 227 North Joanna Avenue in Tavares, Florida. Our institution serves a variety of vibrant communities in Central Florida, including Mount Dora, Seaplane City, Eustis, Howey Mansion, Orlando, Winter Park, Leesburg, and more. Each of these areas offers unique attractions and amenities, from quaint small-town charm to bustling city life. Our team of real estate advisors is dedicated to helping clients find their perfect home in these diverse communities. Whether you're looking for a retirement retreat, a lakefront property, a modern construction, or a historic mansion, we have the expertise to guide you through the process. With homes ranging in price from $95,000 to over a million, we can help you find a property that fits your budget and lifestyle.

Pointon Realty is a finance and real estate agency located at 751 South Main Street, Winter Garden, Florida, United States. Our commitment to you goes beyond providing personalized attention and service. Learn why hundreds of families and investors have chosen us for the purchase or sale of their property. Hear fantastic stories of people who have come to the US with their families or to invest, facing challenges, surprises, and adaptation. Our numbers are official data from the Orlando Regional REALTORS® Association - ORRA. Watch the video for a market analysis from the Broker of Pointon Realty. Whether you're looking for Vacation Homes, Residential Housing, or Land to Build, we have access to the entire real estate market to offer you the best options. Find your dream home with us, no matter the price or size, what matters is calling it home. Access the best residential condominiums for annual rental investment. Earn income in dollars with a vacation home in one of Orlando's Resorts, the city that thrives on tourism all year round. We are the first Brazilian real estate agency in Orlando to be a member of the REALTORS® Land Institute. We offer high-quality professional services to sell your property quickly and safely. Get to know the most impressive and modern Vacation Home Resort in Orlando at the moment. One of the residential condominiums closest to the Disney™ parks and commercial area. Andrea, our leader, has earned her place as an immigrant entrepreneur and leads one of the most recognized real estate agencies in Orlando. She receives numerous awards and continuously strives to improve professionally, serving entrepreneurs, investors, and families who trust in her professionalism and success for these important decisions. Leave a testimonial and help others get to know us better. Your actions are your differential. You don't sell just to sell - you are transparent and protect your client. The assistance you offer after the sale establishes a bond of friendship between you and the client. This is the best endorsement a professional can have. Join us in achieving success in the hottest market in the US. Your American Dream starts here! Follow our social media to stay informed. Winter Garden is a small, charming city planned by Disney™ and exudes quality of life. Lake Nona is synonymous with modernity, innovation, and well-being. Discover the number one city in Florida to raise a family.

Nikki Ansons, Disney area REALTOR® is a top-rated real estate agency located at 400 South Park Avenue, Winter Park, Florida, United States. With a reputation for exceptional service, Nikki Ansons goes above and beyond for her clients, ensuring a smooth and stress-free experience when buying or selling a home. Clients have praised Nikki for her excellent communication skills, in-depth knowledge of the property market, and ability to provide timely and thorough answers to any questions. With a wide network of associates, Nikki can connect clients with all the additional services they may need, making the selling process seamless and efficient.

Home Away Orlando is a reputable real estate agency located at 400 West Fairbanks Avenue in Winter Park, Florida. Our team of experienced agents are dedicated to helping clients find their perfect home away from home in the Orlando area. Whether you are looking for a vacation rental, investment property, or permanent residence, we are here to assist you every step of the way. With a wide range of listings to choose from and a commitment to exceptional customer service, Home Away Orlando is the go-to agency for all your real estate needs in the Sunshine State. Contact us today to start your property search and make your dream of owning a piece of Orlando a reality.