The 30 Best Island vacation rentals in Destin, Florida

Welcome to Pine Island Cove, a hidden gem nestled on Pine Island near Flamingo Bay in Saint James City, Florida. Located at 7290 Ladyfish Drive, our charming lodging and RV park offers a serene escape into Old Florida's nature. Surrounded by the abundant wildlife, including majestic eagles and ospreys, Pine Island Cove is the perfect destination for nature enthusiasts and those seeking tranquility. Renowned for some of the best fishing spots in the world, our over-55 community attracts visitors from across the country and beyond, many of whom have come to affectionately call it "The Cove" or simply "Home." Whether you’re looking to relax or explore, Pine Island Cove provides a welcoming atmosphere where you can unwind and connect with the natural beauty of Florida. Come experience the charm and tranquility of Pine Island Cove, where every stay feels like coming home.

Welcome to JW Marriott Marco Island Beach Resort, your premier destination for luxury and relaxation in the heart of Marco Island, Florida. Located at 400 South Collier Boulevard, our resort offers an unparalleled experience along three miles of pristine, private beaches on the stunning Gulf of Mexico. Immerse yourself in sophisticated elegance as you enjoy a wide array of amenities designed to make your stay exceptional. Whether you are here for a business retreat, a family vacation, or a romantic getaway, our resort caters to your every need. Indulge in global cuisine at any of our 12 dining venues, test your skills on one of two championship golf courses, or rejuvenate at our exquisite spa with luxurious treatments and massages.

Welcome to Beach on Marco Island, your ultimate destination for relaxation and adventure on the stunning shores of Marco Island, Florida. Nestled in the heart of Florida's Paradise Coast, our prime location at Marco Island, FL 34145, offers visitors a perfect blend of natural beauty and modern amenities. At Beach on Marco Island, we pride ourselves on providing an unforgettable experience for every guest. Whether you're seeking a tranquil escape under the sun, exciting water sports, or a picturesque backdrop for your family gatherings, our pristine beaches cater to all your needs. Enjoy sunbathing on soft, white sands, take a refreshing dip in the crystal-clear waters of the Gulf of Mexico, or explore the vibrant marine life with snorkeling and kayaking adventures.

Welcome to South Beach, Marco Island, your premier destination for relaxation and enjoyment in the heart of Florida's Paradise Coast. Conveniently located at 671 County Road 951, Marco Island, Florida, our establishment offers a unique blend of natural beauty and modern amenities, ensuring a memorable experience for all our visitors. At South Beach, Marco Island, you'll find pristine sandy shores, crystal-clear waters, and breathtaking sunsets, making it the perfect spot for beachgoers and nature lovers alike. Whether you're looking to unwind under the sun, take a refreshing swim, or enjoy a leisurely stroll along the coastline, our beach provides an idyllic setting for all your seaside adventures.

Welcome to Perdido Key Area of Gulf Islands National Seashore Discover the natural beauty and rich history of the Perdido Key Area, a premier tourist attraction located at 13333 Johnson Beach Road, Pensacola, Florida. Nestled along the stunning Gulf of Mexico, our destination offers an unforgettable experience with its emerald coast waters, magnificent white beaches, fertile marshes, and historical landscapes.

Welcome to Island Tides Vacation Rental, your premier destination for unforgettable getaways on the stunning Gulf Coast. Located at 1110 Via De Luna Drive, Pensacola Beach, Florida, our business combines the expertise of a real estate and travel agency to offer you the finest selection of vacation properties. Whether you're seeking a serene escape or a family adventure, we have the perfect accommodations to suit your needs. Explore our diverse portfolio of 33 meticulously curated properties, each offering unique experiences and luxurious amenities. From the pet-friendly charm of Aloha by the Sea, with its breathtaking views and wrap-around porch, to the opulence of Aqua Palms, featuring a private heated pool and spacious lawn, your ideal vacation home awaits.

Welcome to Clearwater Beach PaddleBoard & Rental, your ultimate destination for all your beach adventure needs in Clearwater, Florida! Conveniently located at 439 Poinsettia Avenue, just next to the Clearwater Beach Visitor Center, we offer a wide range of rentals and gear to enhance your coastal experience. Whether you're looking to explore the stunning waters on a paddleboard, kayak through the serene harbor, or simply cruise along the beachfront on a bicycle, we have everything you need. Our extensive rental inventory includes paddleboards, kayaks, bikes, fishing poles, beach chairs, umbrellas, and much more. We even offer electric bicycles for those looking to add a bit of excitement to their ride.

Welcome to Clearwater Beach Scooter and Bike Rentals, your go-to destination for fun and convenient transportation in beautiful Clearwater Beach, Florida! Located at 619 South Gulfview Boulevard, behind Shephard’s Beach Resort, we offer a fantastic selection of rental options to suit your beachside adventures. Choose from our new Kymco scooters, 3-Speed Beach Cruiser bikes, or stylish golf carts equipped with Bluetooth audio and LED lights. Our quick and easy rental process ensures you spend more time enjoying the sights and sounds of Clearwater Beach. Whether you're cruising along the coast on a scooter, exploring town on a bike, or making a statement with one of our golf carts, we have flexible rental options available by the hour, day, or week.

Welcome to Beach Vibe Cycle Rentals, your premier destination for exploring the stunning coastal beauty of St. Pete Beach and beyond. Conveniently located at 4615 Gulf Boulevard, St. Pete Beach, Florida, we offer a wide range of high-quality bicycles perfect for discovering the local gems of the area. Whether you're cruising through the charming streets of Pass-a-Grille, venturing out to the scenic Fort de Soto, or enjoying the vibrant atmosphere of Treasure Island, our rentals are designed to enhance your adventure. With access to the renowned Pinellas Trail, our cycles provide an excellent way to soak up the sun and enjoy the breathtaking views Florida has to offer. We also offer exclusive local memberships and exciting sightseeing and sunset tours for those looking to experience the area in a unique way.

Welcome to The Pedaling Pelican Bike Rental, your go-to destination for exploring the stunning landscapes of St. Petersburg, Florida, on two wheels. Located conveniently at 3500 Pinellas Bayway S, St. Petersburg, FL 33715, we offer an extensive range of high-quality bikes suitable for all ages and skill levels, making it easy for you to embark on an unforgettable adventure. Whether you're a local resident or a visitor, you'll find our services tailored to meet your needs. We provide seamless online access to bike rentals, reservations, and payments, available 24/7 for your convenience. Discover the breathtaking beauty of Fort De Soto Park, renowned for its rich ecology and historical significance, all while enjoying a leisurely bike ride. With over 1,136 acres of interconnected islands, the park is home to diverse ecosystems, including mangroves, wetlands, and palm hammocks. Spot some of the 328 documented bird species or witness the nesting loggerhead sea turtles along the pristine beaches.

Welcome to Billy's Rentals, your premier destination for unforgettable adventures on Sanibel Island! Conveniently located at 1470 Periwinkle Way, Sanibel, Florida, Billy's Rentals has been serving locals and tourists alike with top-quality rental services and exceptional customer care. Explore the beautiful island with our wide range of bicycles, including tandem and children's bikes, perfect for family outings or solo adventures. For those looking to hit the water, we offer a variety of beach equipment and water sports rentals, such as paddleboards, kayaks, and beach chairs, ensuring you have everything you need for a day of fun in the sun.

Welcome to Tyler & Tyler (Chair & Umbrella Rental), your go-to destination for a relaxing day at the stunning Madeira Beach, Florida. Conveniently located at 15100 Gulf Boulevard, our family-owned business specializes in providing comfortable and affordable chair and umbrella rentals to enhance your beach experience. Whether you're planning a peaceful solo retreat or a fun-filled family outing, Tyler & Tyler ensures you have everything you need to enjoy the sun and surf in style. Our premium rental equipment is designed for maximum comfort and durability, allowing you to unwind and soak up the breathtaking views of the Gulf Coast. As a beloved local tourist attraction, we're dedicated to making your visit to Madeira Beach unforgettable. Stop by and let us help you create lasting memories under the sun. Your perfect beach day starts here!

Welcome to Island Harbor Marina, a charming and historic marina nestled in the heart of Palm Harbor, Florida. Conveniently located at 123 Orange Street, just 1/2 mile off the Intracoastal Waterway, our marina offers easy access to some of the most beautiful destinations in the area, including Honeymoon Island, Caladesi Island, and Three Rooker Bar. Established as a fish camp in the 1940s, Island Harbor Marina has been a beloved family-owned business for generations. Over the years, we've grown and evolved while maintaining our quaint and welcoming atmosphere, making it the perfect spot to launch your boating adventures.

Welcome to Anna Maria Island Tours, your gateway to unforgettable island adventures! Located at 314 Pine Avenue, Anna Maria, Florida, our local business is dedicated to providing exceptional experiences that immerse you in the natural beauty and rich culture of Anna Maria Island. Whether you're exploring by boat, paddle, bike, or on foot, we offer personalized tours that reveal the stunning waters, picturesque coasts, and charming streets of this idyllic destination. Embark on an exclusive private boat tour led by our skilled Captain. With flexible options ranging from 3 to 6 hours, you can tailor your journey to suit your schedule and preferences. Accommodating up to 6 passengers, our tours ensure a customized and unforgettable maritime experience. Explore our pricing options based on your chosen duration and group size, and discover the magic of the island's waterways.

Welcome to Ana Maria Island, your premier tourist attraction located at Florida 789, Bradenton Beach, Florida. Nestled in the heart of the beautiful Gulf Coast, Ana Maria Island offers a unique blend of natural beauty, vibrant culture, and endless recreational opportunities. Whether you're seeking a relaxing beach retreat or an adventure-filled getaway, our island paradise has something for everyone. Explore pristine white sand beaches, crystal-clear turquoise waters, and stunning sunsets that paint the sky with breathtaking colors. Enjoy a variety of outdoor activities, including swimming, snorkeling, fishing, and kayaking. Discover charming boutiques, local art galleries, and delightful dining options that showcase the rich flavors of Florida cuisine.

Welcome to Upper Picnic Island Beach, a serene oasis located in the vibrant city of Tampa, Florida. Nestled along the picturesque shoreline, our park offers a perfect escape for families, nature enthusiasts, and anyone looking to unwind amidst nature's beauty. At Upper Picnic Island Beach, you'll find pristine sandy beaches, lush green spaces, and breathtaking views of the sparkling waters. Our park is an ideal spot for picnicking, sunbathing, or simply enjoying a leisurely stroll. With well-maintained facilities, including picnic tables, grills, and clean restrooms, we ensure a comfortable and enjoyable experience for all our visitors.

Welcome to Pine Island Airport, your gateway to the beautiful and serene Pine Island, Florida. Conveniently located at 13350 Morningstar Lane, Bokeelia, our airport offers easy access to the stunning landscapes and vibrant communities of the region. Whether you're visiting for leisure or business, Pine Island Airport provides a seamless travel experience with its well-maintained facilities and friendly service. Our airport is designed to accommodate private and charter flights, ensuring a personalized and efficient journey for all travelers. We pride ourselves on offering a relaxed and welcoming atmosphere, reflecting the charm and hospitality of Pine Island itself. With our commitment to safety and customer satisfaction, you can trust Pine Island Airport to deliver a high-quality travel experience.

Welcome to Pine Island Partners LLC, your serene getaway nestled in the heart of Saint James City, Florida. Located in the picturesque setting of Pine Island, our park offers a tranquil escape from the hustle and bustle of everyday life. Whether you're a local resident or a visitor exploring the beautiful sunshine state, Pine Island Partners LLC provides the perfect backdrop for relaxation and recreation. Our park is designed to cater to nature lovers and outdoor enthusiasts, offering a variety of amenities and activities for all ages. Stroll through our lush landscapes, enjoy a peaceful picnic, or engage in bird watching as you immerse yourself in the natural beauty of Florida's unique ecosystem. With well-maintained walking trails and open spaces, Pine Island Partners LLC is ideal for families, friends, and solo adventurers seeking a peaceful retreat.

Welcome to Island Beach Houses, your premier destination for exquisite beachfront living and unforgettable travel experiences in Indian Rocks Beach, Florida. Nestled at 1101 Gulf Boulevard, our dual-service agency specializes in offering stunning real estate opportunities and personalized travel services tailored to your coastal lifestyle dreams. As a leading real estate agency, Island Beach Houses is dedicated to helping you find your perfect slice of paradise along the pristine shores of Indian Rocks Beach. Whether you're looking to purchase a luxurious beachfront property, invest in a vacation rental, or explore long-term leasing options, our team of experienced real estate professionals is here to guide you every step of the way.

Welcome to Island in the Sun Realty, your premier destination for exceptional lodging and real estate services in Largo, Florida. Conveniently located at 1001 Starkey Road, our versatile business is dedicated to meeting all your accommodation and property needs in the heart of the Sunshine State. At Island in the Sun Realty, we offer a unique blend of services, including a top-notch real estate agency, a serene RV park, and comfortable lodging options to suit a variety of preferences. Whether you're looking to find your dream home, invest in prime real estate, or simply enjoy a relaxing getaway in our well-maintained RV park, our experienced and friendly team is here to assist you.

Welcome to Marco Island Real Estate LLC, your premier destination for all your real estate needs on the beautiful Marco Island, Florida. Conveniently located at 1095 Bald Eagle Drive, our agency is dedicated to providing exceptional service and expertise to both buyers and sellers in the vibrant Marco Island community. At Marco Island Real Estate LLC, we pride ourselves on our in-depth knowledge of the local market and our commitment to finding the perfect property to suit your lifestyle and investment goals. Whether you're searching for a luxurious waterfront home, a cozy condo with stunning views, or a prime piece of land to build your dream house, our experienced team is here to guide you every step of the way.

Welcome to Marco Island Real Estate, your premier destination for exceptional real estate services in the heart of paradise. Conveniently located at 900 North Collier Boulevard, Marco Island, Florida, we are dedicated to helping you find your dream home or investment property in this stunning coastal community. As a leading real estate agency, we offer a comprehensive range of services tailored to meet the needs of buyers, sellers, and investors alike. Our team of experienced and knowledgeable agents is committed to providing personalized service, ensuring a seamless and stress-free experience from start to finish. Whether you're seeking a luxurious beachfront estate, a cozy island getaway, or a lucrative investment opportunity, we have the expertise and local insights to guide you every step of the way.

Welcome to Fort Myers Beach Vacations/Sunny Daze, your premier destination for unforgettable getaways and real estate opportunities on the stunning shores of Fort Myers Beach, Florida. Located at 612 Estero Boulevard, our dedicated team is committed to helping you discover the perfect vacation rental or property investment in this tropical paradise. As both a real estate and travel agency, we offer a unique blend of services to meet all your needs. Whether you're seeking a relaxing beachfront retreat, an adventurous island excursion, or a lucrative real estate investment, we provide personalized assistance and expert advice to turn your vision into reality.

Welcome to the Naples, Marco Island, Everglades Convention and Visitors Bureau (CVB), your premier source for discovering the unparalleled beauty and vibrant culture of Southwest Florida. Conveniently located at 2660 Horseshoe Drive North, Naples, Florida, our local government office is dedicated to promoting the picturesque destinations of Naples, Marco Island, and the Everglades. Whether you are a resident, visitor, or business owner, our team is here to provide you with comprehensive information and resources to enhance your experience in this stunning region. Explore pristine beaches, world-class dining, and thrilling outdoor adventures, all while enjoying the warm hospitality and unique charm of our communities. Visit us to learn more about upcoming events, travel planning, and how we can assist you in making the most of your time in paradise.

Welcome to Keewaydin Island Beach, a pristine paradise located in the heart of Florida's natural beauty. Situated at Florida 34113, United States, Keewaydin Island Beach is a premier tourist attraction that offers visitors an unforgettable escape into nature’s wonders. This hidden gem is renowned for its untouched white sandy beaches, crystal-clear waters, and abundant wildlife, providing a serene retreat for nature lovers and adventure seekers alike. Accessible only by boat, Keewaydin Island Beach promises a unique and tranquil experience away from the hustle and bustle of city life. Whether you're looking to relax under the sun, enjoy a leisurely picnic, or explore the island's diverse ecosystems, there's something for everyone. The island is a haven for shell collectors, bird watchers, and fishing enthusiasts, offering endless opportunities to connect with nature.

Welcome to Isles of Capri Vacation Rentals, your premier destination for unforgettable getaways in the heart of Florida's paradise. Nestled at 219 Capri Boulevard in the picturesque Naples area, our agency specializes in providing exceptional real estate and travel services tailored to your dream vacation needs. Whether you’re seeking a serene waterfront escape or a luxurious island retreat, our diverse portfolio of properties promises something for every traveler. At Isles of Capri Vacation Rentals, we pride ourselves on offering personalized service and expert local knowledge to help you discover the hidden gems of the Isles of Capri. Our dedicated team is committed to ensuring your stay is seamless and memorable, from the moment you book until your departure. Explore pristine beaches, enjoy world-class dining, and indulge in the vibrant local culture, all while staying in comfort and style.

Welcome to Macaluso's Marco Rentals, your premier destination for exceptional real estate and travel services on beautiful Marco Island, Florida. Conveniently located at 438 Kendall Drive, Marco Island, FL 34145, our dedicated team is committed to helping you discover the perfect property or plan an unforgettable vacation in paradise. As a trusted real estate agency, Macaluso's Marco Rentals specializes in offering a wide range of properties, from luxurious waterfront homes to charming condos, catering to both buyers and renters. Our experienced agents provide personalized service to ensure you find a property that perfectly suits your lifestyle and investment goals.

Welcome to your tropical getaway at Marco Island Lodging, nestled in the heart of beautiful Marco Island, Florida. Conveniently located at 600 South Collier Boulevard, our premier lodging establishment offers a serene escape just steps away from the pristine beaches and sparkling waters of the Gulf of Mexico. At Marco Island Lodging, we pride ourselves on providing exceptional comfort and hospitality. Our well-appointed accommodations are designed to cater to your every need, whether you're here for a family vacation, a romantic retreat, or a solo adventure. Each room is equipped with modern amenities, ensuring a relaxing and enjoyable stay.

Welcome to Amelia Island Slingshot, your ultimate destination for adventure and exploration in beautiful Fernandina Beach, Florida. Located conveniently at 1943 South 8th Street, our business offers an exhilarating way to experience the stunning landscapes and vibrant local culture of Amelia Island. Whether you're a thrill-seeker or simply looking to enjoy a leisurely drive, our top-of-the-line Slingshot vehicles provide the perfect blend of excitement, comfort, and style. At Amelia Island Slingshot, we pride ourselves on delivering exceptional customer service and ensuring a memorable experience for every guest. Our fleet of well-maintained, three-wheeled Slingshots is available for both short-term rentals and extended adventures, allowing you to explore Amelia Island at your own pace. Discover the island's scenic coastal roads, charming historic sites, and breathtaking beaches from the unique perspective of our open-air vehicles.

Welcome to Amelia Island Mobile Home Park, your premier lodging and RV park destination nestled in the serene surroundings of Fernandina Beach, Florida. Conveniently located at 2031 Russell Road, our park offers a perfect blend of comfort and natural beauty, providing an ideal escape for travelers seeking relaxation and adventure. At Amelia Island Mobile Home Park, we pride ourselves on offering a welcoming and well-maintained environment for both short-term visitors and long-term residents. Our spacious lots are designed to accommodate a variety of mobile homes and RVs, ensuring you have all the space you need to settle in comfortably. Each site is equipped with essential amenities, including water, electricity, and sewer hookups, to make your stay as convenient as possible.