The 30 Best Beach vacation rentals in Winter Springs, Florida

Welcome to Beach Chill Inn, located at 13446 Gulf Boulevard in Madeira Beach, Florida, United States. Our lodging institution offers a relaxing and comfortable stay by the ocean. Book in the spring and save using the code SPRING20. Whether you prefer the East Coast's bustling boardwalks, the Gulf Coast's fishing opportunities, or the laidback surf of the West Coast, Beach Chill Inn has something for everyone. Enjoy amenities like direct beach access, oceanfront homes, pools, hot tubs, and pet-friendly stays.

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.

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.

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.

Holiday Beach Rentals is a premier real estate and travel agency located at 17762 Ashley Drive in Panama City Beach, Florida. With a wide selection of vacation rentals, from beachfront condos to cozy cottages, we offer the perfect accommodations for your next getaway. Our experienced team is dedicated to providing top-notch customer service and ensuring that your vacation is stress-free and enjoyable. Whether you're looking for a relaxing beach retreat or an action-packed adventure, Holiday Beach Rentals has the perfect property for you. Book your dream vacation with us today and experience the beauty of Panama City Beach!

Sugar Beach Rentals Inc is a premier real estate and travel agency located at 2827 Joan Avenue in Panama City Beach, Florida. Specializing in vacation rentals and property management, we offer a wide selection of beachfront properties for your perfect getaway. Our experienced team is dedicated to providing top-notch service and helping you find the ideal rental for your needs. Whether you are looking for a cozy condo for a romantic escape or a spacious beach house for a family vacation, we have something for everyone. Contact us today to start planning your dream beach vacation in beautiful Panama City Beach.

Vacation Rentals in Seagrove Beach is a premier real estate and travel agency located at 40 Sea Walk Circle in Santa Rosa Beach, Florida. We specialize in providing luxurious and comfortable vacation rentals in the beautiful Seagrove Beach area. Our team of experienced professionals is dedicated to helping you find the perfect rental property for your next getaway. Whether you're looking for a beachfront condo, a cozy cottage, or a spacious villa, we have a wide selection of properties to choose from. Let us help you plan the perfect vacation in Seagrove Beach!

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.

Bay Pointe Vacation Rentals is a premier real estate and travel agency located in the picturesque town of Bonita Springs, Florida. Situated at 5900 Bonita Beach Road Southwest, our agency specializes in providing luxury vacation rentals for those looking to escape the hustle and bustle of everyday life. Whether you're seeking a beachfront villa or a cozy cottage nestled in a quiet neighborhood, our team of experienced agents is dedicated to helping you find the perfect getaway. With a wide selection of properties to choose from, Bay Pointe Vacation Rentals is your go-to destination for an unforgettable vacation experience in beautiful Bonita Springs.

Seasonal Rental offers luxurious vacation properties located at 126 Teryl Road in the stunning city of Naples, Florida. Our properties are perfect for those looking to escape the cold winter months or simply enjoy a relaxing getaway in the Sunshine State. With a range of amenities and beautiful surroundings, Seasonal Rental provides the perfect home away from home for your next vacation. Whether you're looking for a beachfront villa or a cozy condo, we have the perfect rental for you. Book your stay with Seasonal Rental and experience the ultimate vacation in Naples, Florida.

Florida Rentals by the Gulf, LLC is a premier real estate and travel agency located in the beautiful city of Bonita Springs, Florida. Our agency specializes in providing top-notch vacation rental properties along the stunning Gulf Coast. Whether you are looking for a beachfront condo or a luxurious villa, we have the perfect accommodation to suit your needs. Our team of experienced agents is dedicated to helping you find the ideal rental for your next vacation. Contact us today to start planning your dream getaway in sunny Florida!

Welcome to our vacation rental located at 5414 Darlene Street in Spring Hill, Florida, United States. Our lodging facility offers a comfortable and convenient place to stay for your next vacation. With spacious accommodations and all the amenities you need for a relaxing stay, our vacation rental is the perfect home away from home. Whether you're exploring the local attractions or simply enjoying some downtime, our rental is the ideal choice for your getaway. Book your stay with us today and experience the comfort and convenience of our vacation rental in Spring Hill, Florida.

Miramar Beach Vacation Rentals by Vacasa offers a wide selection of beach houses, condos, and resort-style accommodations in the beautiful resort town of Miramar Beach, Florida. Located just down the road from Destin, our rentals provide the perfect getaway for families, couples, and even furry friends with dog-friendly options available. With over 1600 rentals offering internet access, professional housekeeping services, and amenities like private pools, guests can relax and enjoy all that Miramar Beach has to offer. From stunning beaches and world-class golf courses to shopping and dining options, there is something for everyone to enjoy in this picturesque area. Whether you're looking for a short-term vacation rental or a long-term stay as a snowbird, Miramar Beach Vacation Rentals by Vacasa has the perfect accommodations for your Florida Gulf Coast getaway."

Snowbird Beach Rental of Panama City Beach is a premier real estate and travel agency located at 6503 Sunset Avenue in Panama City, Florida. We specialize in providing luxurious beachfront rental properties for snowbirds looking to escape the cold winter months and enjoy the sun and sand of Panama City Beach. Our expert team is dedicated to helping you find the perfect rental property to suit your needs and make your stay unforgettable. Whether you're looking for a cozy condo or a spacious beach house, we have a wide selection of properties to choose from. Contact us today to start planning your dream vacation on the beautiful shores of Panama City Beach.

Dunedin Vacation Rentals is a reputable real estate and travel agency located at 234 Florida Avenue in Dunedin, Florida, United States. We specialize in offering a wide range of vacation rental properties in the beautiful city of Dunedin, catering to all types of travelers looking for a comfortable and convenient accommodation option. Our dedicated team of professionals is committed to providing exceptional customer service and ensuring that your vacation experience is unforgettable. Whether you are looking for a cozy beachfront condo or a spacious family home, Dunedin Vacation Rentals has the perfect property for your next getaway. Book with us today and let us help you create lasting memories in Dunedin!

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.

Siesta Key Vacation Rentals is a premier real estate and travel agency located at 8900 Blind Pass Road in Siesta Key, Florida. We specialize in providing luxurious vacation rentals for visitors looking to experience the beauty and relaxation of Siesta Key. Our properties are meticulously maintained and offer top-notch amenities to ensure a comfortable and unforgettable stay. Whether you're looking for a beachfront condo or a cozy cottage, we have a wide range of options to suit your needs. Let Siesta Key Vacation Rentals help you plan your dream vacation in this stunning tropical paradise.

Stays Orlando is a premier real estate agency located at 2330 Ponce de Leon in Coral Gables, Florida, United States. Specializing in vacation rentals, Stays Orlando offers a wide selection of vacation homes near Disney for families looking to enjoy a memorable getaway. Rent a home with Stays Orlando and make the most of your family vacation experience.

Best Vacation Deals is a leading travel agency located at 7200 Lake Ellenor Drive in Orlando, Florida. We specialize in providing our clients with the most affordable and exciting vacation packages to destinations around the world. Our experienced team of travel experts work tirelessly to ensure that every aspect of your trip is taken care of, from flights and accommodations to activities and excursions. Whether you're looking for a relaxing beach getaway, a thrilling adventure tour, or a romantic honeymoon destination, Best Vacation Deals has the perfect package for you. Contact us today to start planning your dream vacation!

Palm Beach County Vacation Rentals By Owner is a premier real estate and travel agency located in Las Palmas Park, Boynton Beach, Florida, United States. We specialize in providing vacation rentals for visitors looking to experience the beauty and luxury of Palm Beach County. Our team of professionals are dedicated to helping you find the perfect rental property for your vacation, whether you're looking for a beachfront condo or a spacious villa. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Contact us today to start planning your dream vacation in Palm Beach County!

Dream Vacations - Glenn and Associates is a premier travel agency located in Panama City, Florida. Our team of experienced travel professionals is dedicated to helping you plan the vacation of your dreams. Whether you're looking for a relaxing beach getaway, an adventure-filled cruise, or a cultural exploration, we can help you create the perfect itinerary. With personalized service and attention to detail, we strive to make your travel experience unforgettable. Visit us at 8826 North Lagoon Drive and let us turn your travel dreams into reality.

Sunchaser Vacations is a premier real estate and travel agency located at 10901 Front Beach Road in Panama City Beach, Florida, United States. Specializing in vacation rentals, property management, and travel planning, Sunchaser Vacations offers a wide range of services to help clients find the perfect getaway. Whether you're looking for a beachfront condo, a cozy cottage, or a luxury villa, our team of experienced agents is dedicated to helping you make the most of your vacation experience. Contact Sunchaser Vacations today to start planning your next unforgettable trip to the beautiful beaches of Panama City Beach.

Citistar Vacation Rentals is a premier real estate and travel agency located at 7328 Thomas Drive in Panama City, Florida. We specialize in providing top-quality vacation rental properties for those looking to experience the beauty and excitement of the Gulf Coast. Our dedicated team of professionals is committed to helping clients find the perfect accommodations for their stay, whether it's a cozy beachfront condo or a spacious luxury villa. With a wide range of properties to choose from, we strive to make every guest's vacation unforgettable. Contact us today to start planning your dream getaway with Citistar Vacation Rentals.

Florida On Vacation is a premier real estate and travel agency located at Tuscany Way in Davenport, Florida, United States. Specializing in vacation rentals and property management, our experienced team is dedicated to helping clients find the perfect accommodation for their Florida getaway. Whether you're looking for a cozy beachfront condo or a luxurious villa with a private pool, we have a wide range of options to suit every budget and preference. Let us help you plan your dream vacation in the Sunshine State!

Anchorage Vacation Rental is a premier real estate and travel agency located at 135 Anchorage Street in Fort Myers Beach, Florida, United States. We specialize in providing luxurious vacation rental properties for visitors looking to experience the beauty and charm of the area. Our team of experienced professionals is dedicated to helping you find the perfect accommodations for your stay, whether you're looking for a cozy beachfront condo or a spacious waterfront villa. With a wide range of options to choose from, we are committed to making your vacation experience unforgettable. Contact us today to book your dream vacation rental in Fort Myers Beach!

Yellow Vacations is a premier travel agency located at 9852 Emerald Berry Drive in Winter Garden, Florida. Specializing in creating unforgettable travel experiences, our team of expert agents is dedicated to helping you plan the perfect vacation. Whether you're looking for a relaxing beach getaway, an adventurous outdoor expedition, or a luxurious cruise, Yellow Vacations has you covered. With personalized service and attention to detail, we strive to make your dream vacation a reality. Contact us today to start planning your next adventure!

Vacation Experts is a premier travel agency located in Miami, Florida. Our team of experienced and knowledgeable travel experts are dedicated to helping you plan the perfect vacation tailored to your needs and preferences. Whether you're looking for a relaxing beach getaway, a thrilling adventure, or a cultural exploration, we have the expertise to make your dream vacation a reality. Visit us at 13714 Southwest 90th Avenue and let us be your guide to unforgettable travel experiences.

Outpost Rentals is a premier rental agency located at 1255 West 9 Mile Road in Pensacola, Florida. We offer a wide range of rental options including apartments, condos, houses, and vacation homes in the beautiful coastal city of Pensacola. Our properties are well-maintained and fully equipped to provide a comfortable and enjoyable stay for our guests. Whether you are looking for a short-term rental or a long-term lease, Outpost Rentals has the perfect accommodation for you. Our friendly and professional staff are dedicated to ensuring that your rental experience is stress-free and memorable. Contact us today to book your next stay in sunny Pensacola!

Welcome to Clearwater Beach Restaurant, your premier dining destination located at 333 Coronado Drive in the heart of beautiful Clearwater, Florida. Nestled just steps away from the pristine shores of Clearwater Beach, our restaurant offers a delightful culinary experience that perfectly complements the stunning coastal scenery. At Clearwater Beach Restaurant, we pride ourselves on serving a diverse menu that caters to all tastes. Our chefs use the freshest local ingredients to craft mouthwatering dishes that range from succulent seafood and juicy steaks to vibrant salads and hearty pastas. Whether you're in the mood for a casual lunch, a romantic dinner, or a family gathering, our inviting atmosphere and friendly service ensure a memorable dining experience for all.

Welcome to Sunny Rentals, your premier destination for unforgettable vacation experiences in the heart of Sarasota, Florida. Conveniently located at 57 South Boulevard of the Presidents, our business is dedicated to providing you with top-quality rental services that cater to all your leisure needs. Nestled in the vibrant community of Sarasota, just steps away from pristine beaches and a lively cultural scene, Sunny Rentals offers a diverse selection of accommodations and recreational equipment to enhance your stay. Whether you're seeking a cozy beachside cottage, a luxurious waterfront condo, or the perfect gear for outdoor adventures, our friendly and knowledgeable team is here to ensure a seamless and enjoyable experience. Explore the beauty of Sarasota with Sunny Rentals and discover why we are the preferred choice for travelers seeking comfort, convenience, and exceptional service. Visit us today and let us help you create memories that will last a lifetime.