TOP 30 Best Vacation cottage rentals in Winter Garden, Florida

Vacation Club Life - DVC Resales & Rentals is a real estate agency located at 1106 Brick Road, Winter Garden, Florida, United States. With a 100% retention rate amongst satisfied clients worldwide, we are dedicated to providing exceptional service to those looking to buy or sell Disney Vacation Club (DVC) points. Situated only steps away from Walt Disney World Resorts and the Magic Kingdom, we share our client's passion for DVC experiences and pride ourselves on our long-standing reputation, friendships, and partnerships. Our team, led by the nicest and most patient broker Rachel, is committed to helping clients make successful bids and navigate the DVC resale process with ease. Glenn, who handles contracts, is equally attentive and ensures that all transactions are smooth and stress-free. Clients have praised us for our great service, attentiveness, and knowledge, making us a highly recommended firm in the industry.

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.

Hampton Inn Winter Haven is a charming lodging institution located at 202 Cypress Gardens Boulevard in Winter Haven, Florida, United States. This cozy hotel offers comfortable rooms with modern amenities, a complimentary hot breakfast, and a fitness center for guests to enjoy. Conveniently situated near local attractions such as Legoland Florida Resort and the Chain of Lakes, Hampton Inn Winter Haven is the perfect choice for travelers looking for a relaxing stay in a beautiful setting. Whether you're visiting for business or leisure, you'll find everything you need for a memorable stay at this welcoming hotel.

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.

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.

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.

Garden Views Realty is a premier real estate agency located at 1106 Brick Road in Winter Garden, Florida, United States. Specializing in residential and commercial properties, our team of experienced agents is dedicated to helping clients find their dream home or investment property. With a focus on personalized service and attention to detail, we strive to make the buying or selling process as smooth and stress-free as possible. Whether you're looking to buy, sell, or rent, Garden Views Realty is here to help you navigate the real estate market with ease. Contact us today to start your real estate journey!

Avis Car Rental, located at 448 Cypress Gardens Boulevard in Winter Haven, Florida, offers a variety of car rental options for your convenience. With a special offer of one day free on select car rentals, you can explore the Sunshine State with ease. Whether you're visiting for business or pleasure, Avis has you covered with a range of vehicles from compact cars to luxury sedans and even 15-passenger vans for larger groups. With convenient pick-up and drop-off locations, including at the Orlando International Airport, Avis makes it easy for you to get where you need to go. Book your rental today and start your Florida adventure!

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.

Econo Lodge Winter Haven Chain of Lakes is a cozy and affordable lodging option located at 5665 Cypress Gardens Boulevard in Winter Haven, Florida, United States. Situated near the beautiful Chain of Lakes, this establishment offers comfortable rooms and convenient amenities for guests to enjoy during their stay. Whether you are visiting for business or leisure, Econo Lodge Winter Haven Chain of Lakes is the perfect choice for a relaxing and enjoyable stay in the Sunshine State.

Vacation Rentals is a premier real estate and travel agency located at 10611 Front Beach Road in Panama City Beach, Florida, United States. We specialize in providing top-notch accommodations for vacationers looking to experience the beauty and excitement of the Gulf Coast. Our expert team is dedicated to helping you find the perfect rental property for your next getaway, whether you're seeking a cozy beachfront condo or a spacious luxury villa. With a wide range of options to choose from, we make it easy to plan a memorable and stress-free vacation. Contact us today to start planning your dream vacation in Panama City Beach!

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.

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.

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.

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.

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.

Island Real Estate of Anna Maria Island, Inc. is a premier real estate and travel agency located at 6101 Marina Drive, Holmes Beach, Florida, United States. Specializing in vacation rentals on the beautiful Anna Maria Island, our agency offers a wide range of beachfront properties with stunning views of the Gulf of Mexico. With over 50 years of experience, our dedicated staff is committed to providing top-notch customer service and ensuring that every guest has a relaxing and memorable stay. From cozy beachfront cottages to luxurious oceanfront mansions, we have the perfect rental for every taste and budget. Our team of local experts are available 24/7 to assist with any questions or concerns, and can provide recommendations for the best local spots and experiences to enjoy during your stay. Whether you're looking for a quick getaway or a long-term investment, Island Real Estate has you covered. Book your Anna Maria Island rental today and experience the beauty and charm of Florida's hidden gem.

"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.

Castnetter Beach Resorts is a charming lodging located at 4102 4th Avenue in Holmes Beach, Florida. Nestled just steps away from the pristine shores of the Gulf of Mexico, this resort offers a relaxing and luxurious getaway for guests looking to unwind and soak up the sun. With spacious and beautifully appointed rooms, a sparkling outdoor pool, and easy access to the beach, Castnetter Beach Resorts is the perfect destination for a beach vacation. Whether you're looking to relax on the sand, explore the local shops and restaurants, or simply enjoy the stunning ocean views, this resort has everything you need for a memorable stay. Book your stay today and experience the beauty of Holmes Beach at Castnetter Beach Resorts.

Located at 325 South Gulfview Boulevard in Clearwater, Florida, The Beachview Inn Clearwater Beach is the perfect destination for those looking to experience the warm sun, white sandy beaches, and soothing gulf breezes of beautiful Clearwater Beach. With the motto of "Rest. Play. Repeat.", the goal of The Beachview is to take relaxation to the next level...sea level. Situated across Beachwalk, guests can easily kick off their flip flops, dig their toes into the sand, and escape from the stresses of everyday life. The Beachview offers breathtaking views of Clearwater Beach during the day, and guests can enjoy poolside firepits at dusk while taking in an unforgettable sunset. Whether guests are seeking romance, relaxation, or family time, The Beachview provides exceptional service, a friendly atmosphere, and modern accommodations to cater to all needs.

Welcome to Beach House RV Resort, your ideal getaway nestled in the heart of Largo, Florida. Located at 12121 Vonn Road, our full-service RV park offers a perfect blend of relaxation and adventure, just ten minutes away from the serene, warm waters of the Gulf of Mexico. Positioned centrally between Clearwater and Saint Petersburg in picturesque Pinellas County, our resort is the perfect base for exploring some of Florida's top attractions, including Busch Gardens, Disney World, and Universal Studios, all within a ninety-minute drive. At Beach House RV Resort, we cater to all your camping and lodging needs with our well-equipped RV campsites, each featuring full hookups, patios, and picnic tables. Whether you're here to soak up the sun on the stunning Indian Rocks Beaches just two miles away or to enjoy the vibrant vacation lifestyle of the Suncoast, we have something for everyone. Our prime location also ensures you're never far from an array of shopping, dining, and golfing opportunities.

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.

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.

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.

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.

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!

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.