TOP 30 Best Florida vacation rentals in Winter Haven, Florida

Central Florida Watersports and Boat Rentals is a renowned institution located in Winter Haven, Florida, United States. As a school specializing in watersports and boat rentals, they provide top-quality instruction and equipment for individuals looking to explore the beautiful waterways of Central Florida. Whether you are a beginner or an experienced water enthusiast, their expert staff is dedicated to ensuring a safe and enjoyable experience on the water. With a prime location on Lake Howard Drive Southwest, Central Florida Watersports and Boat Rentals is the perfect destination for anyone looking to have a memorable and exciting day out on the water.

The Stones Real Estate Firm in Winter Haven, Florida, is a trusted real estate agency with a proven track record of serving over 1000 families in Polk County. With innovative marketing strategies and a global reach, our dedicated team of Realtors is ready to help you achieve your real estate goals. Led by Michael Stone and Deanna Stone, our firm sets the standard for excellence in the industry. With over 20 years of experience, we offer expert guidance and cutting-edge technology to ensure a flawless experience for our clients. Whether you are buying or selling, choose The Stones Real Estate Firm for exceptional results. Contact us today at 863-412-9733 or 863-412-2080.

Island Vacation Travel Agency LLC, located on Crown Street in Winter Haven, Florida, is a premier travel agency that specializes in creating unforgettable island vacations. Our team of experienced travel experts is dedicated to helping our clients plan the perfect getaway, whether it's a relaxing beach vacation, an adventurous island-hopping tour, or a luxurious resort stay. At Island Vacation Travel Agency LLC, we understand the importance of staying informed and up-to-date on travel advisories and requirements, especially in light of the ongoing Covid-19 pandemic. We closely follow the guidelines set forth by the CDC and provide essential travel advice to ensure the safety and well-being of our clients.

Courtyard by Marriott Winter Haven is a welcoming and modern lodging institution located at 6225 Cypress Gardens Boulevard in Winter Haven, Florida, United States. This hotel offers comfortable and spacious rooms, a convenient location near local attractions such as Legoland Florida Resort, and top-notch amenities including a fitness center, outdoor pool, and on-site dining options. Whether you are visiting for business or leisure, Courtyard by Marriott Winter Haven provides a relaxing and enjoyable stay for all guests.

Best Western Plus Winter Haven Inn & Suites is a charming lodging establishment located at 5801 Roosevelt Drive Southeast in Winter Haven, Florida, United States. This modern hotel offers comfortable rooms and suites, along with a range of amenities including a fitness center, outdoor pool, and complimentary breakfast. Conveniently situated near popular attractions such as LEGOLAND Florida Resort and Winter Haven Chain of Lakes, this hotel is the perfect choice for both leisure and business travelers. With friendly staff and a welcoming atmosphere, Best Western Plus Winter Haven Inn & Suites ensures a pleasant stay for all guests.

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.

Holiday Inn Winter Haven, an IHG Hotel, is a charming lodging option located at 200 Cypress Gardens Boulevard in Winter Haven, Florida, United States. This hotel offers comfortable and well-appointed rooms, a range of modern amenities, and friendly service to ensure a pleasant stay for guests. Conveniently situated near popular attractions such as LEGOLAND Florida Resort and Cypress Gardens, this hotel is the perfect base for exploring the area. Whether you are visiting for business or leisure, Holiday Inn Winter Haven provides a welcoming and relaxing atmosphere for all guests.

Haven Beach Rentals is a real estate and travel agency located at 17757 Front Beach Road in Panama City Beach, Florida, United States. Our guests have consistently had amazing experiences staying in our beautiful condos. They are immaculately clean, comfy, and beautifully furnished with everything you need for a perfect stay. Our units are equipped with extra amenities that set us apart from other rentals, such as fully stocked kitchens, multiple coffee makers, and mixers. The convenience of having beach chairs available for use adds to the overall experience. Our team at Haven Beach Rentals, led by Kendall and Lisa, ensures that your time in the condo goes smoothly. They are easy to work with and go above and beyond to make sure everything is satisfactory. Many guests have expressed their desire to book with us again, as they could not have asked for better accommodations. The only downside for them is having to leave at the end of their stay.

Welcome to Lake Lulu Short Term Home Rental, your perfect lakeside paradise located at 516 Lake Lulu Drive in Winter Haven, Florida. This 4-bedroom, 3-bath vacation rental is ideal for your 'Sunshine State' getaway, offering luxury amenities such as a 26-foot dock, swimming pool, hot tub, gazebo bar, and game room. Enjoy water skiing, wakeboarding, and fishing on Lake Lulu right from your doorstep, or relax by the pool and soak up the Florida sun. The house is conveniently located near the Chain of Lakes, Legoland, and a variety of lakeside restaurants that you can reach by boat.

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.

East Haven RV Park is a charming lodging destination situated at 4320 Dundee Road in Winter Haven, Florida. This peaceful retreat offers a serene atmosphere for guests looking to escape the hustle and bustle of everyday life. The park features spacious RV sites with full hook-ups, making it the perfect spot for travelers exploring the Sunshine State. Surrounded by lush greenery and tranquil surroundings, East Haven RV Park provides a relaxing environment for guests to unwind and enjoy the beauty of nature. With its convenient location and top-notch amenities, this RV park is a must-visit destination for anyone looking to experience the beauty of Florida.

The Winter Haven Hotel, Miami Beach, Autograph Collection is a luxurious lodging option located at 1400 Ocean Drive in the vibrant city of Miami Beach, Florida, United States. This elegant institution offers a unique and personalized experience for guests, with beautifully designed rooms and upscale amenities. Situated right on the iconic Ocean Drive, guests can enjoy stunning views of the beach and easy access to the city's top attractions. Whether you're looking for a relaxing beach getaway or a stylish urban retreat, the Winter Haven Hotel is the perfect choice for your stay in Miami Beach.

Lake Roy Beach Inn Winter Haven is a charming lodging institution located at 1823 Cypress Gardens Boulevard in Winter Haven, Florida. Our largest room is a spacious 3 bedroom/2 bathroom townhouse suite with a kitchen, perfect for accommodating large groups and families. The midsize room options include 2 double beds or 1 king bed, with a television and a living space containing a full kitchen, sofa, and porch. For those without a kitchen, our Deluxe Rooms offer lake and beachfront views with 2 separate bedrooms. Situated on the famous "Chain O' Lakes," Lake Roy Beach Inn is the only lakefront hotel in Winter Haven with a private sandy beach. We are just minutes away from LEGOLAND® Florida, a popular theme park for families with children. Due to the pandemic, we have temporarily postponed our complimentary breakfast service for safety reasons.

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.

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!

Regency Inn of Winter Haven is a cozy and comfortable lodging option located at 3525 Lake Alfred Road in Winter Haven, Florida. Situated in the heart of the United States, this charming inn offers a warm and inviting atmosphere for guests looking for a relaxing stay. With spacious rooms, modern amenities, and friendly staff, Regency Inn is the perfect choice for travelers seeking a home away from home. Whether you're visiting for business or pleasure, you'll enjoy the convenient location and excellent service at this lovely establishment. Book your stay at Regency Inn of Winter Haven today and experience true Southern hospitality at its finest.

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.

Travelodge by Wyndham Winter Haven is a cozy and convenient lodging option located at 2275 8th Street Northwest in Winter Haven, Florida. Situated in a prime location, this hotel offers comfortable and spacious rooms, perfect for both business and leisure travelers. Guests can enjoy amenities such as free Wi-Fi, a complimentary continental breakfast, and a refreshing outdoor pool. The friendly staff is always ready to assist with any needs or questions, making your stay enjoyable and hassle-free. Whether you are visiting Winter Haven for work or play, Travelodge by Wyndham is the perfect home away from home.

Malak Real Estate is a reputable real estate agency located at 407 1st Street South in Winter Haven, Florida, United States. With a team of experienced and dedicated professionals, Malak Real Estate is committed to providing top-notch services to help clients buy, sell, or rent properties in the area. Whether you are looking for a new home, an investment property, or commercial real estate, Malak Real Estate has the expertise and resources to assist you every step of the way. Contact us today to learn more about how we can help you achieve your real estate goals.

Cruise Planners is a premier travel agency located at 1258 Zambrana Ct in Winter Haven, Florida, United States. Specializing in cruise vacations, they offer expert advice, personalized service, and exclusive deals to ensure a memorable and stress-free travel experience. With a wide range of cruise options and destinations to choose from, Cruise Planners is your go-to destination for all your vacation planning needs. Contact them today to start planning your dream cruise getaway!

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.

The World Barefoot Center, located at 3915 Conine Drive East in Winter Haven, Florida, is a premier school and store dedicated to the sport of barefoot water skiing. Founded by world-renowned barefoot water skier Keith St. Onge, the center offers expert coaching, state-of-the-art equipment, and a welcoming community for enthusiasts of all levels. Whether you are a beginner looking to learn the basics or a seasoned pro seeking to improve your skills, the World Barefoot Center is the perfect destination for all your barefoot water skiing needs.

RE/MAX Heritage Professionals is a renowned real estate agency located at 264 West Central Avenue in Winter Haven, Florida, United States. Our team of experienced professionals is dedicated to providing top-notch service to our clients, whether they are buying, selling, or renting properties. With a strong focus on customer satisfaction and a deep knowledge of the local real estate market, we strive to help our clients achieve their real estate goals. Contact us today to experience the expertise and professionalism of RE/MAX Heritage Professionals.

Lakefront Investment Group is a premier real estate agency located in Winter Haven, Florida. Situated at 786 Avenue C Southwest, this institution specializes in helping clients buy, sell, and invest in properties along the picturesque lakefronts of the area. With a team of experienced and knowledgeable real estate professionals, Lakefront Investment Group offers personalized services to assist clients in achieving their real estate goals. Whether you are looking for a dream lakefront property or seeking to maximize your investment potential, Lakefront Investment Group is dedicated to providing exceptional service and expertise to help you navigate the real estate market with confidence.

Lake Ashton Golf Club is a premier golfing destination located at 4000 Mulligan Lane in Winter Haven, Florida. This stunning club offers two championship golf courses surrounded by picturesque views of the surrounding lakes and natural beauty. With top-notch facilities, professional staff, and meticulously maintained courses, Lake Ashton Golf Club provides an exceptional experience for golfers of all skill levels. Whether you're looking to improve your game, enjoy a round with friends, or simply take in the serene surroundings, this club is the perfect place to unwind and indulge in the sport you love.

Four Lakes Golf Club Retirement Community is a premier retirement destination located in Winter Haven, Florida. This all-inclusive community offers a wide range of amenities including a beautiful golf course, luxury lodging options, real estate services, a top-rated restaurant, and a convenient RV park for visitors. Residents can enjoy a peaceful and active lifestyle surrounded by lush landscapes and serene lakes. Come experience the ultimate retirement living at Four Lakes Golf Club Retirement Community.

"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.

Tupelo Vue is a charming institution located at 525 Avenue G Northwest in Winter Haven, Florida, United States. This cozy establishment offers a welcoming atmosphere and a wide range of services to cater to the needs of its guests. From comfortable accommodations to delicious dining options, Tupelo Vue ensures a memorable stay for all visitors. Whether you are looking for a relaxing getaway or a convenient place to stay while exploring the city, Tupelo Vue is the perfect choice for your next trip to Winter Haven.

Welcome to Country Lakes Villages, your serene escape nestled in the heart of Palmetto, Florida. Located at 6100 Bayshore Road, our picturesque RV park offers a perfect blend of comfort, community, and natural beauty. Whether you're planning a short getaway or an extended stay, Country Lakes Villages provides an ideal setting for relaxation and adventure. Our well-maintained facilities are designed to cater to all your lodging needs, featuring spacious RV sites equipped with modern amenities. Enjoy the tranquility of our lush surroundings, complete with scenic lakes and abundant wildlife, offering a peaceful retreat from the hustle and bustle of everyday life.

Welcome to Sun Valley, your premier destination for lodging and RV park experiences in Tarpon Springs, Florida. Nestled at 39248 U.S. 19, our location offers the perfect blend of tranquility and accessibility, situated on Florida’s stunning Gulf Coast. Sun Valley is your gateway to the vibrant cities of St. Petersburg, Clearwater, and Tampa Bay, yet it remains a peaceful retreat from the hustle and bustle. Designed for those aged 55 , Sun Valley is more than just a place to stay—it's a lifestyle. Our community is brimming with resort-style amenities, engaging activities, and a welcoming atmosphere that makes every day feel like a vacation. Whether you're escaping the chilly winters or seeking a year-round haven, Sun Valley promises an active, fulfilling lifestyle.