TOP 30 Island vacation rentals in Madeira Beach, Florida

13 results found

Island Paradise Cottages of Madeira Beach offers a relaxing and picturesque retreat for visitors to the sunny shores of Florida. Nestled in the heart of Madeira Beach, this charming lodging institution provides cozy and well-appointed cottages for guests to enjoy during their stay. Just a short walk from the beach, guests can soak up the sun, swim in the crystal-clear waters, or simply unwind on the sandy shores. With its convenient location and comfortable accommodations, Island Paradise Cottages is the perfect choice for a memorable beach getaway in Madeira Beach.

Island Gulf Resort is a charming lodging establishment located at 13912 Gulf Boulevard in Madeira Beach, Florida. Situated along the stunning Gulf of Mexico, this resort offers guests a tranquil and picturesque retreat. The resort features comfortable accommodations, including spacious rooms and suites with modern amenities. Guests can relax by the outdoor pool, soak up the sun on the nearby sandy beaches, or explore the local shops and restaurants. With its prime location and welcoming atmosphere, Island Gulf Resort is the perfect destination for a relaxing beach getaway in the heart of Florida.

Caddy's Beach Apartments is a real estate and travel agency located at 9001 West Gulf Boulevard in Treasure Island, Florida, United States. At Caddy's Waterfront locations, visitors can enjoy the best happy hour specials along Florida's Gulf Coast, with drink specials available at Caddy's locations in Clearwater, Tampa Bay, and Bradenton. Caddy's Treasure Island, Madeira Beach, John's Pass, Indian Shores, and Bradenton locations offer live music Sunset Sessions, where guests can grab a drink and enjoy the beat. Visitors can also earn rewards points for every $1 spent at Caddy's and view the Happy Hour specials, cocktail of the month, and other drink promotions. Private Beach Cabanas for breakfast, daytime, or sunset events can be booked at Caddy's, and seasonal food highlighting seafood and American cuisine is available. Come visit Caddy's Beach Apartments for a memorable experience on the Florida coast.

iTrip Vacations - St Petersburg Beaches is a real estate and travel agency located at 13999 Gulf Boulevard in Madeira Beach, Florida, United States. Specializing in short-term rentals, they offer professional property management services for owners looking to maximize their rental income without the stress. Located in the beautiful coastal city of Oceanside, California, iTrip Vacations offers family-friendly activities and experiences for the ultimate vacation memories. From scenic beaches to historic landmarks, cultural experiences, and outdoor adventures, Oceanside has something for everyone.

Elite Beach Vacation Rentals is a family-owned real estate and travel agency located at 1886 West Bay Drive in Largo, Florida. Our newly renovated and modern vacation rentals are perfect for guests looking to experience the beauty of the Gulf Coast beaches. From beachfront condos to waterfront homes, we offer a variety of unique spaces for you to create lifelong vacation memories. Our No Worry guest experience ensures that your stay with us is stress-free from start to finish. Whether you're looking to stay in Indian Rocks Beach, Indian Shores, Largo, Redington Shores, Redington Beach, Madeira Beach, or Treasure Island, we have the perfect vacation rental for you. You can easily search for rentals online or contact our friendly reservation agents for assistance.

Welcome to Goin' Coastal Golf Cart Rental & Bike Shop, your premier destination for golf cart and e-bike rentals in Indian Rocks Beach, Florida. Conveniently located at 311 Gulf Boulevard, our locally veteran-owned and operated business proudly serves the surrounding areas, including Belleair Beach, Clearwater Beach, Indian Shores, Madeira Beach, N. Redington Beach, Redington Beach, Sand Key, and Treasure Island. As Indian Rocks Beach's original provider of eco-friendly golf carts and e-bikes, we are committed to minimizing our carbon footprint while maximizing your vacation experience. Our fleet features brand-new, fully-loaded Bintelli golf carts, equipped with all the latest amenities, including Bluetooth speakers and vibrant night lights, ensuring a fun and memorable ride.

Changing Tides Cottages is a charming lodging institution located at 225 Boca Ciega Drive in Madeira Beach, Florida. Situated just steps away from the pristine beaches of the Gulf Coast, this cozy getaway offers guests a peaceful retreat in a beautiful tropical setting. The cottages are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Whether you're looking to relax by the pool, explore the nearby attractions, or simply soak in the stunning ocean views, Changing Tides Cottages is the perfect destination for a memorable vacation.

Dockside Condos is a real estate and travel agency located at 445 South Hamden Drive in Clearwater, Florida. Stay with us and experience the beauty of Clearwater Beach, voted the Number 1 Best Beach in the United States by tripadvisor in 2018 and 2019. Our waterfront and beachfront rentals offer a convenient location near popular areas such as St. Petersburg, Tampa, St. Pete Beach, Treasure Island, Indian Shores, and Madeira Beach. Come relax and enjoy all that Clearwater Beach and Tampa Bay have to offer at Dockside Condos.

B&W Management, Inc. is a real estate and travel agency located at 11 Idlewild Street in Clearwater, Florida, United States. Search for vacation rentals by your arrival and departure dates, with arrangements possible for off-season stays. Beach Bobby Rowe offers tips for preparing to stay in vacation rentals on Clearwater Beach. Enjoy your stay on the award-winning Clearwater Beach, ranked as the number one beach in the United States by TripAdvisor in 2018 and 2019, and the number six beach in the world. B&W Management offers beachfront rentals and condominium rentals in Clearwater Beach, Florida, conveniently located near St. Petersburg, Tampa, St. Pete Beach, Treasure Island, Indian Shores, Madeira Beach, and all of Tampa Bay. Book your vacation rental with B&W Management, Inc. for a memorable beach getaway.

John's Pass Condos is a real estate and travel agency located at 12924 Gulf Boulevard in Madeira Beach, Florida. Our condos are ideally situated just steps away from historic John's Pass Village and Boardwalk, offering a wide range of retail outlets, dining options, and activities for the whole family to enjoy. With easy access to nearby beaches like Clearwater Beach and St Pete Beach via the Free Beach Ride Service or Suncoast Beach Trolley, our location is perfect for exploring the Gulf Coast. We offer newly furnished 1, 2, and 3 bedroom beachfront rental condos at various properties including Beach Place, Sandy Shores, Surf Song, Madeira Bay Resort, Villa Madeira, and Madeira Norte. Each condo is designed to provide the ideal vacation environment with amenities such as secure buildings, heated outdoor swimming pools, BBQ grills, and private balconies. Our condos also come fully equipped with cable TV, Wi-Fi, and fully equipped kitchens.

Islamorada Turtle Tours LLC is a travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Cruise Islamorada aboard its newest, biggest, and best tour boat, "The Turtle", a custom-built 53ft XL Deck Boat that can accommodate up to 42 people. Explore beautiful Islamorada on one of our spectacular tours, departing daily from The Lorelei Restaurant & Cabana Bar. On our tours, you can enjoy a short cruise to the famous Islamorada sandbar, where you can walk along the sandy flat, float on giant mats, soak up the sun, and relax. Fun for all ages! You can also snorkel at one of Islamorada's beautiful shallow water reefs, with depths between 8-20 feet. The choice of reef location will depend on factors such as visibility and weather conditions.

Welcome to Blackburn Coastal Realty, your trusted partner in exploring the vibrant real estate market of Redington Beach, Florida. Conveniently located at 16330 Gulf Boulevard, our agency specializes in providing exceptional real estate services tailored to meet your unique needs. Whether you're searching for your dream beachfront home, an investment property, or wishing to sell your current residence, our dedicated team of experienced real estate professionals is here to guide you every step of the way. At Blackburn Coastal Realty, we pride ourselves on our deep local knowledge, personalized service, and commitment to helping you achieve your real estate goals. Discover the beauty and charm of coastal living with us today.

Welcome to Total Realty Services, Inc., your premier real estate agency located at 13030 Gulf Lane, Madeira Beach, Florida. Specializing in condo-hotels and seasonal investment properties, we are passionate about selling real estate in the Sunshine State and are experts in the buying and selling of condos across our beautiful Gulf Beaches. Our website is a comprehensive resource for both buyers and sellers, featuring the best real estate tools available. It is easy to use and updated every 15 minutes by the official Realtor®’s database. You can save searches, receive daily email alerts of new listings, price changes, sold data, and market reports, and even use our Interactive Map Search to view properties on a map or refine your search by drawing boundaries around your desired area. Bookmark our page for your home, condo, and investment property searches—it’s the only site you’ll ever need!