The 30 Best Accommodations in Winter Park, Florida

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1 Hotel South Beach is a luxurious lodging institution located at 2341 Collins Avenue in Miami Beach, Florida, United States. Set along a pristine 600-foot stretch of shoreline, this sanctuary offers breathtaking views of the ocean and sustainable design using locally sourced and repurposed materials. Guests can enjoy a spring escape at this beachfront oasis, taking dips in pools and the ocean while refueling at unique dining venues with a $100 resort credit. Rooms are equipped with water filtration systems, recycled glassware, sustainable bed linens, and organic mattresses for a restful stay.

WorldMark Palm-Aire is a charming Southern-style resort located at 2601 North Palm Aire Drive in Pompano Beach, Florida. This quiet and secluded beach resort is just 4 miles away from the bustling attractions of Myrtle Beach. Nestled in a protected bird sanctuary, guests can enjoy the pristine shoreline of the Grand Strand and the sights and sounds of Myrtle Beach while staying in cozy suites. The resort offers a perfect blend of relaxation and adventure, with nearby historic towns, museums, wineries, and outdoor activities to explore. Whether you want to unwind by watching the birds or take part in exciting excursions, WorldMark Palm-Aire has something for everyone.

Eastman's Escape for Healthy Pets is a premier pet care facility located at 3377 Forsyth Road in Winter Park, Florida. Our dedicated team of professionals is committed to providing a safe and nurturing environment for your furry friends. From luxurious accommodations to personalized care plans, we ensure that your pets receive the highest quality of care during their stay with us. Whether your pet needs grooming services, exercise, or just some extra TLC, Eastman's Escape for Healthy Pets is the perfect place for them to relax and thrive. Come visit us today and see why we are the top choice for pet owners in the Winter Park area.

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.

Located at 1288 North Orange Avenue in Winter Park, Florida, The Courtesy is a sophisticated bar offering a unique experience for cocktail enthusiasts. With a focus on providing exceptional service and a welcoming atmosphere, The Courtesy is the perfect spot for a night out with friends or a special date. If you're planning to visit with a group of four or more, be sure to make a table reservation to ensure the best experience. The seating can accommodate gatherings of up to 8-10 people, making it ideal for intimate celebrations or get-togethers.

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.

Roberts River Chickee is a unique camping experience located in the beautiful Everglades National Park in Florida, United States. This campground offers a variety of sites including beach sites, ground sites, and chickee sites. For those looking to stay at Roberts River Chickee, it is important to note that backcountry camping requires staying in designated campsites and all require a boat to reach. Reservations can be made on Recreation.gov up to 3 months in advance, with fees ranging from $21 per group plus $2 per person per night during the winter months.

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.

Florida Vacation offers luxurious lodging in the heart of Orlando, Florida. Our institution is dedicated to providing guests with a comfortable and unforgettable stay in the Sunshine State. Whether you are visiting for a family vacation, a romantic getaway, or a business trip, our accommodations are perfect for all types of travelers. Located in a prime location, guests have easy access to all the attractions, shopping, and dining options that Orlando has to offer. Come experience the magic of Florida Vacation and create lasting memories in this beautiful destination.

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.

Natural Smiles is a dental institution located at 4063 North Goldenrod Road in Winter Park, Florida. Dr. Arias, a passionate and dedicated dentist, leads the team with a goal of providing exceptional care to patients and helping them achieve a beautiful smile. Dr. Arias graduated from the School of Oral Medicine in San Juan, Puerto Rico and completed a General Practice Residency Program at Rochester General Hospital in New York. In addition to her professional pursuits, Dr. Arias enjoys cooking, baking, exercising, and spending time with her family. Walk-ins are welcome at Natural Smiles and will be accommodated on the schedule whenever possible. Visit us today for all your dental health needs.

Dr. Carla Arias is a dedicated dentist located at 4063 North Goldenrod Road, Winter Park, Florida, United States. Dr. Arias has always had a passion for dentistry and helping patients achieve a beautiful smile. She graduated from the School of Oral Medicine in San Juan, Puerto Rico and completed a General Practice Residency Program at Rochester General Hospital in New York. In her free time, Dr. Arias enjoys cooking, baking, exercising, and spending time with her family. Walk-ins are welcome at her practice and will be accommodated as best as possible in her schedule. Visit Dr. Carla Arias for all your dental health needs.

Sunny Apartments offers comfortable and stylish vacation rentals in the heart of North Port, Florida. Located at 412 Torrego Street, our apartments are the perfect choice for travelers looking for a relaxing and enjoyable stay. Our accommodations are fully equipped with modern amenities and are just a short distance away from popular attractions, restaurants, and shopping areas. Whether you are visiting for a weekend getaway or an extended vacation, Sunny Apartments provides a cozy and convenient home away from home. Book your stay with us today and experience the best of Florida hospitality.

Behrle & Associates is a trusted accounting and finance institution located at 6918 Aloma Avenue in Winter Park, Florida. With a team of experienced professionals, they provide a wide range of services to help individuals and businesses with their financial needs. Whether you need assistance with tax preparation, bookkeeping, or financial planning, Behrle & Associates is dedicated to providing top-notch service and personalized solutions. Contact them today to see how they can help you achieve your financial goals.

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.

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.

SeaStay Vacation Rentals, located at 101 Reid Avenue in Port St. Joe, Florida, is a real estate and travel agency specializing in over 230 vacation rentals along the beautiful Forgotten Coast. With a focus on finding the perfect coastal home for your getaway, SeaStay offers a variety of options for families and pets alike. The area boasts stunning white-sand beaches, local businesses, and natural beauty that make it a truly unique vacation destination. Guests have praised SeaStay Vacation Rentals for their clean and comfortable accommodations, convenient locations, and well-stocked kitchens. Whether you're looking to relax on the beach, fish in the Gulf, or explore the nearby attractions, SeaStay has something for everyone. With positive reviews and plans to return, SeaStay Vacation Rentals is the perfect choice for your next vacation on the Forgotten Coast.

Cortland Independence is a luxury apartment community located at 14600 Avenue of the Groves in Winter Garden, Florida. With close proximity to top-rated schools, neighborhood parks, and walking trails, our one, two, and three-bedroom apartments offer a high standard of living in the Independence neighborhood. Enjoy scenic nature preserve views, high kitchen ceilings, and screened patios and balconies in a quiet and safe area. Conveniently located near major employers like Florida Hospital Medical Group and Lockheed Martin, commuting is a breeze for residents. There are plenty of options for weekend activities, including boating on Lake Hancock, attending local festivals, or exploring nearby shopping and dining options. The community has received the Reputation 800 Award and the Kingsley Excellence Award for exceeding industry benchmarks and resident satisfaction.

Ascend Waterleigh Club, located at 9405 Ascend Falls Drive in Winter Garden, Florida, is a premier real estate agency offering luxurious living options. Our apartment floor plans are designed to cater to individual preferences, with open-concept living areas, modern kitchens equipped with Whirlpool® appliances, quartz countertops, and White Shaker cabinetry. The spacious bedrooms feature walk-in closets, and each unit includes a private, screened-in patio or balcony. Whether you're looking for a cozy one-bedroom or a spacious three-bedroom apartment, Ascend Waterleigh Club offers the ultimate in luxury living. In addition to our beautiful apartments, Ascend Waterleigh Club provides a range of on-site amenities for residents to enjoy. These include a 24-hour fitness center, a saltwater pool with daybeds, an entertainment club room, and an activity lawn. Our convenient location near Disney Theme Parks, Flamingo Town Center, and excellent dining options ensures that residents have both comfort and accessibility at their fingertips. With features such as keyless entry, luxury vinyl plank flooring, and pet-friendly accommodations, Ascend Waterleigh Club sets a new standard for opulent living in Winter Garden. Schedule a tour today to experience the lavish lifestyle firsthand.

Seasonal Rentals is a premier real estate agency located at 2122 Parrot's Landing in Avon Park, Florida. Specializing in short-term rental properties, we offer a wide selection of vacation homes, condos, and villas for those looking to escape to the Sunshine State for a few weeks or months. Our experienced team of agents are dedicated to helping clients find the perfect seasonal rental that meets their needs and budget. Whether you're looking for a beachfront property, a golf course villa, or a cozy cabin in the woods, Seasonal Rentals has something for everyone. Contact us today to start planning your next seasonal getaway in beautiful Florida.

Sebring Resort is a charming retreat nestled in the heart of Sebring, Florida, United States. Offering a tranquil and picturesque setting, the resort is the perfect destination for those seeking relaxation and rejuvenation. With comfortable accommodations, a range of amenities, and beautiful surroundings, Sebring Resort provides guests with a memorable and enjoyable stay. Whether you're looking to unwind by the pool, explore the local area, or simply take in the stunning views, Sebring Resort offers something for everyone. Come experience the beauty and serenity of Sebring Resort for yourself.

ApartmentSearch by CORT is a reputable real estate agency located at 1920 Florida 436 in Winter Park, Florida. Our team of experienced agents is dedicated to helping you find the perfect apartment that fits your needs and budget. Whether you are looking for a cozy studio or a spacious family home, we have a wide selection of properties available for rent. With our expertise in the local market and commitment to excellent customer service, we strive to make the apartment hunting process as smooth and stress-free as possible for our clients. Contact us today to start your search for your dream apartment in Winter Park!

La Aloma Apartments is a charming residential complex located at 820 Jamestown Drive in Winter Park, Florida. This institution offers modern and spacious apartments with a variety of floor plans to choose from. Residents can enjoy a range of amenities including a swimming pool, fitness center, and beautifully landscaped grounds. The convenient location provides easy access to shopping, dining, and entertainment options in the surrounding area. With its peaceful atmosphere and excellent customer service, La Aloma Apartments is the perfect place to call home in Winter Park.

Tuscany at Aloma is a luxurious senior living community located at 6999 Aloma Avenue in Winter Park, Florida. Our beautifully landscaped grounds and elegant architecture create a serene and inviting atmosphere for our residents. With a focus on providing personalized care and attention, our dedicated staff is committed to ensuring the well-being and comfort of each individual. Our amenities include spacious living accommodations, gourmet dining options, engaging activities and events, and top-notch medical services. Experience the charm and warmth of Tuscany at Aloma, where every day feels like a retreat in the heart of Florida.

Tropical Escape Vacation Homes is a premier real estate and travel agency located at 8320 Championsgate Boulevard in Davenport, Florida, United States. Our luxurious Orlando vacation rentals are conveniently located near the Walt Disney World Resort and other popular theme parks in the area. Experience the best of Orlando's attractions, dining, and shopping while staying in one of our beautiful homes. Whether you're planning a family retreat, romantic honeymoon, golfer's getaway, or winter escape, we have the perfect vacation rental for you. Our goal is to provide each guest with an unforgettable experience in the heart of Florida.

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.