The 30 Best Florida vacation rentals in Winter Garden, Florida

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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.

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.

White Glove Home Service, located in Palm Beach Gardens, Florida, is a trusted institution that provides exceptional home care services for property owners who are away. With a focus on attention to detail and reliability, White Glove ensures that your home is secure, well-maintained, and ready for your return. From receiving deliveries to monitoring house temperature and humidity, White Glove Home Service goes above and beyond to keep your property in top condition. With a team of dedicated professionals led by Sharon, who has years of experience in home watch services, you can trust that your home is in good hands.

Ivan's Grandma is a charming lodging institution located at 818 Hayley Circle in Winter Garden, Florida, United States. This cozy establishment offers a warm and welcoming atmosphere, perfect for travelers looking for a comfortable and homely place to stay. With personalized service and a convenient location, Ivan's Grandma is the ideal choice for those seeking a relaxing and enjoyable accommodation experience. Whether you are visiting for business or pleasure, you are sure to feel right at home at Ivan's Grandma.

Peaceful Easy Feeling is a real estate and travel agency located at 103 South 39th Street in Mexico Beach, Florida, United States. Stay at one of their amazing properties between April 7th and May 23rd and receive 10% off the nightly rate by using code SPRING24. This newly renovated 2BD/2BA townhome in Oceanside Village offers gulf views and is only steps away from the sugary white sandy beaches. Enjoy views of the community pool and the gulf from all 3 balconies. The property features an open concept kitchen, dining, and living area, with luxury vinyl plank flooring throughout. The spacious living area offers a sleeper sofa, smart TV, and balcony access. The fully stocked kitchen has butcher block countertops, a breakfast bar, and a pantry/laundry room for storage. The dining room table seats 6. The guest bedroom has a comfortable king bed and bunk bed, with a private balcony overlooking the Gulf of Mexico. The master suite features a king bed, day bed, smart TV, en-suite bath with a stand-alone shower, garden tub, and double vanity. Enjoy a romantic evening on the private balcony watching the sunset. The property is close to Mexico Beach Marina and within walking distance of stores and restaurants. Beach gear, chairs, umbrellas, toys, and a beach buggy are provided. The property is not pet-friendly due to severe allergies. Monthly rental rates are available for the winter season. Book your beach vacation at Peaceful Easy Feeling and create unforgettable memories!

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.

FL Hub Properties is a reputable real estate agency located in Winter Haven, Florida. We specialize in helping clients buy, sell, and rent properties in the local area. Our team of experienced agents is dedicated to providing exceptional service and ensuring that our clients find their perfect home or investment property. Whether you are looking for a cozy starter home or a luxurious vacation retreat, FL Hub Properties is here to help you every step of the way. Visit us at 3395 Cypress Gardens Road to start your real estate journey today.

Citravest Management is a reputable financial institution located at 30 West Smith Street in Winter Garden, Florida, United States. With a focus on investment management and financial planning, Citravest Management offers personalized services to help clients achieve their financial goals. Their team of experienced professionals is dedicated to providing expert advice and guidance in areas such as asset allocation, risk management, and wealth preservation. Whether you are looking to grow your portfolio or plan for retirement, Citravest Management is committed to helping you make informed decisions and secure your financial future.

The Pro Agent Group is a premier real estate agency and travel agency located at 780 Orange Belt Loop in Winter Garden, Florida, United States. Our expert team specializes in helping clients navigate the rapidly growing and changing Orlando residential market to maximize their dollars whether buying or selling a home. With over 30 years of experience in real estate brokerage, Keith Courtney and his team provide first-rate customer service, attention to detail, and dedicated follow-through to ensure clients receive unsurpassed service. In addition to our residential home division, The Pro Agent Group also offers guidance in purchasing vacation homes near Disney that are filled with fun amenities such as theaters, game rooms, and themed kids' bedrooms. Our vacation home division, led by Keith and Katie, aims to maximize each client's dollars and provide top-notch customer service.

The Real Estate Collection is a reputable real estate agency located at 100 West Plant Street in Winter Garden, Florida. Led by the Central Florida RE Team, Kimberly Beach-Byerly & Erica Sadelfeld, this agency offers a wide range of properties for sale in the area. The listing information is regularly updated and provided by the Daytona Beach Area Association of REALTORS® Multiple Listing Service. Consumers can browse through properties based on price range and find detailed information about each listing. The agency participates in cooperative data exchange programs with multiple listing services to ensure a comprehensive database of available properties. While the information provided is deemed reliable, it is recommended that interested parties verify the details before making a purchase decision. The agency adheres to federal laws prohibiting discrimination in the sale, rental, or financing of housing based on race, color, religion, sex, handicap, familial status, or national origin. Whether you are looking to buy or sell a property in Winter Garden, The Real Estate Collection is a trusted partner in your real estate journey.

David Dorman, REALTOR is a reputable real estate agency located at 2747 Maguire Road in Ocoee, Florida, United States. Specializing in Central Florida real estate, David Dorman is dedicated to helping clients with buying, selling, relocating, or investing in properties in Orlando, Ocoee, Winter Garden, Windermere, Gotha, and surrounding areas. With a focus on utilizing the latest marketing technologies and strategies, David Dorman ensures that clients receive top-notch service and expertise throughout their real estate transactions. From providing mortgage information to offering a global marketing plan, David Dorman goes above and beyond to meet the unique needs of each client. With a strong commitment to giving back to the community, David Dorman is actively involved with charitable organizations such as Easterseals of Central Florida and Shepherd’s Hope. Whether you are a first-time homebuyer or a seasoned investor, David Dorman, REALTOR is your go-to source for all your Central Florida real estate needs.

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.

Villa Lazy River - with Pool & Hot Tub in Bonita Springs The Villa Lazy River will immediately impress you upon arrival. Park in your long driveway or in your double garage. Step inside and be enchanted by the ambiance of this brightly furnished villa with a large pool. Enjoy your vacation with us, you deserve it.

Kelly French Real Estate is a top-rated real estate agency located at 3554 West Orange Country Club Drive, Winter Garden, Florida. Specializing in Orlando Investments, Short Term Rentals, Vacation Homes, and Second Homes in Central Florida and beyond, Kelly French Real Estate, LLC is dedicated to assisting both international and U.S. absentee owners with buying and selling properties. With Kelly French ranked #158 out of 26,000 local agents in 2024, you can trust that you are working with one of the best in the industry. Our team is committed to providing excellent service and negotiating on your behalf for all of your real estate needs. Whether you are looking for an investment property, vacation home, or second home, Kelly French Real Estate is here to help you find the property of your dreams. Contact us today at 352-988-4975 for assistance in navigating our website or searching for real estate.

Valstar Realty is a leading real estate agency located at 5728 Major Boulevard in Orlando, Florida. Our experienced agents are dedicated to helping you find the perfect property to match your preferences, location, and lifestyle. Whether you are buying, selling, or leasing, we have you covered with a strategic approach and marketing plan to ensure success. With our expansive network, we are able to open doors for our clients on all sides of the property equation. We are committed to staying involved throughout all stages of the real estate process and providing reliable information that is independently reviewed and verified.

Orlando Fun Villas is a charming vacation rental institution located at 7070 Spring Park Drive in Winter Garden, Florida, United States. Offering a variety of spacious and beautifully decorated villas, guests can enjoy a comfortable and luxurious stay while exploring all that Orlando has to offer. With convenient access to major attractions such as Walt Disney World, Universal Studios, and SeaWorld, Orlando Fun Villas is the perfect home base for a fun-filled vacation. Whether you're seeking relaxation by the pool or excitement at the theme parks, this institution has everything you need for an unforgettable getaway.

Daniel Wilson - Top Orlando Living - RE/MAX is a premier real estate agency located at 1155 Louisiana Avenue in Winter Park, Florida. Our team of professional and experienced RE/MAX agents specialize in meeting the needs of home buyers and sellers in the Central Florida area. Whether you are a first-time buyer, local resident, relocator, or homeowner looking to sell or upgrade, we offer personalized service to ensure a smooth and enjoyable real estate transaction. We specialize in Downtown Orlando and surrounding areas such as College Park, Thornton Park, Winter Park, Maitland, Lake Nona, Oviedo, Winter Springs, Longwood, Lake Mary, Apopka, Altamonte Springs, Waterford Lakes, Kissimmee, Doctor Phillips, Winter Garden, Horizon West, and Windermere. Trust Top Orlando Living at RE/MAX 200 Realty for all your real estate needs.

Concierge Realty Inc is a premier travel agency located at 15568 Avenue Of The Arbors in Winter Garden, Florida. With a team of dedicated professionals, they offer personalized and luxurious travel experiences for their clients. Whether you're looking for a relaxing beach getaway, a thrilling adventure in the mountains, or a cultural exploration in a vibrant city, Concierge Realty Inc can create the perfect itinerary for you. Their attention to detail and commitment to customer satisfaction set them apart as a top choice for all your travel needs. Experience the world in style with Concierge Realty Inc.

Resort Tours & Accommodations is a premier travel agency located at 13360 West Colonial Drive in Winter Garden, Florida. Specializing in providing top-notch tour packages and accommodations, we offer a wide range of services to cater to all your travel needs. Whether you're looking for a relaxing beach getaway, an adventurous mountain expedition, or a luxurious resort experience, our experienced team is here to help you plan the perfect vacation. With our personalized service and attention to detail, you can trust Resort Tours & Accommodations to make your travel dreams a reality. Visit us today and start planning your next unforgettable journey.

Bass Online Fishing Guides is located at 456 Amethyst Avenue in Auburndale, Florida, United States. Situated in the heart of Winter Haven's famous Chain of Lakes, our institution offers expert fishing guides who have a minimum of 20 years of experience navigating the Central Florida waters. The Winter Haven Chain of Lakes is a boater's paradise, with 16 interconnected lakes connected by navigable canals. The area is known as the world's water skiing capital, making it a popular destination for water sports enthusiasts. Our fishing guides are carefully selected from the best in the area and are insured, US Coast Guard licensed captains. Each trip includes a fully equipped Bass boat, fuel, and tackle, ensuring a memorable and safe experience for all guests. Whether you're a seasoned angler or a beginner, our guides will provide you with the fishing trip of a lifetime.

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 Bradenton Tropical Palms, your serene getaway in the heart of Bradenton, Florida. Conveniently located at 2310 14th Street West, our charming RV park offers a perfect blend of comfort and convenience for travelers seeking a relaxing retreat. Whether you're planning a short stay or an extended vacation, our lush, tropical environment provides a picturesque setting to unwind and enjoy the beauty of Florida's Gulf Coast. At Bradenton Tropical Palms, guests can take advantage of our well-maintained facilities, including spacious RV sites equipped with full hookups, modern amenities, and complimentary Wi-Fi. Our friendly, attentive staff is dedicated to ensuring your stay is enjoyable and stress-free.