The 30 Best Vacation rentals on the gulf coast in Madeira Beach, Florida

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.

Sunset Beach Suites is a charming lodging institution located at 14231 Gulf Boulevard in Madeira Beach, Florida. Situated right on the stunning Gulf Coast, this beachfront property offers spacious suites with breathtaking views of the ocean and easy access to the sandy shores. Guests can relax and unwind in the comfortable accommodations, take a dip in the outdoor pool, or simply soak up the sun on the private beach. With its convenient location and friendly staff, Sunset Beach Suites is the perfect destination for a relaxing beach getaway in the Sunshine State.

Madeira Beach 1 is a popular tourist attraction located at 12774 Florida 699 in Redington Shores, Florida, United States. This institution offers visitors a chance to experience the beauty and charm of the Gulf Coast with its pristine sandy beaches, crystal clear waters, and stunning sunsets. Whether you're looking to relax on the beach, go fishing, or explore the local shops and restaurants, Madeira Beach 1 has something for everyone. Come and discover why this destination is a favorite among travelers from all over the world.

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.

Shores of Madeira Condominiums, located at 15400 Gulf Boulevard in Madeira Beach, Florida, is the perfect retreat for those seeking tranquility and relaxation. This real estate and travel agency offers direct beachfront rentals with a minimum stay of 30 days, ensuring a peaceful and uninterrupted experience for guests. The complex features a large heated pool, jacuzzi, and lounge chairs overlooking the Gulf of Mexico, as well as common areas with a barbecue grill and indoor lounge. Situated across the street from restaurants, bars, and a supermarket, Shores of Madeira offers convenience and comfort for longer term customers. During the peak season from January to April, guests are required to arrive on the 1st of the month and stay for a minimum of 4 weeks. Reservations are limited to 4-week increments, and flexibility for booking in other months is available by contacting the reservation line. The condo association mandates an application approval process at least 30 days prior to arrival, ensuring a secure and seamless experience for all guests.

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.

Crimson on the Gulf is a premier real estate and travel agency located at 12935 Gulf Lane in Madeira Beach, Florida, United States. Situated directly on the beach, Crimson Resort offers luxurious amenities such as private balconies, a heated pool, WiFi, and washer/dryers in every unit. The two-bedroom units can accommodate up to four guests, while the three-bedroom units can accommodate up to six guests, making it the perfect destination for families looking to enjoy a beach vacation together. Many units have been recently remodeled with high-end finishes, ensuring a comfortable and stylish stay. The property is non-smoking, including all private balconies and common areas. Guests can also enjoy a hot tub next to the beachfront pool, secure key and code access to the building, an onsite office for convenience, and charcoal grills for BBQs near the pool area. For a relaxing and unforgettable beach getaway, look no further than Crimson on the Gulf.

Levique Tours and Rentals is a bar and travel agency located at 15015 Madeira Way in Madeira Beach, Florida. Specializing in crafting water sport experiences on Florida's Gulf Coast, they offer a variety of activities such as jet ski rentals, tiki boat cruises, kayak and paddle board rentals, as well as SeaDoo Jet Ski and Moped Scooter rentals. Whether you're looking for excitement or relaxation, Levique Tours and Rentals has something for everyone. Customers rave about the friendly and knowledgeable staff, with Captain Bob, Kohlton, and Julie receiving high praise. With options for group tours or private rentals, this is the #1 place in Madeira Beach to experience all of your favorite water and land activities. Visit Levique Tours and Rentals for an unforgettable adventure on the beautiful Gulf Coast of Florida.

Welcome to Archibald Memorial Beach Park, your ultimate beachfront destination in Madeira Beach, Florida. Conveniently located at 15100 Gulf Boulevard, our park offers ample metered parking spots just steps away from the pristine sandy shores. Enjoy easy access to the beach via four wooden walkovers and make use of our well-maintained public restrooms and two outdoor shower areas to refresh after a day in the sun. For those looking to relax and unwind, our covered picnic area provides a perfect spot for a seaside meal. Sports enthusiasts can enjoy a game at one of our two sand beach volleyball courts. On-site, The Snack Shak offers a delightful selection of meals and beverages, perfect for enjoying while taking in the stunning beach views.

Welcome to Madeira Beach Yacht Club Condo Rental, your premier travel agency for an unforgettable stay in the heart of Florida's stunning Gulf Coast. Located at 320H Medallion Boulevard, St. Petersburg, Florida, our agency specializes in offering luxurious condo rentals that provide the perfect blend of comfort and breathtaking views. Nestled in the vibrant community of Madeira Beach, our accommodations are just steps away from pristine beaches, vibrant nightlife, and exquisite dining options. Our condos are fully equipped with modern amenities, ensuring a comfortable and relaxing stay for families, couples, and solo travelers alike. Whether you're here to unwind on the sandy shores, explore the local attractions, or enjoy water sports, Madeira Beach Yacht Club Condo Rental is your gateway to an unforgettable Floridian experience. Our friendly team is dedicated to providing personalized service, helping you plan every detail of your stay to ensure it’s nothing short of perfect.

Welcome to Stoke Beach, your ultimate escape nestled in the heart of Madeira Beach, Florida. Located at 14950 Florida 699, our stunning beach destination offers a perfect blend of natural beauty and recreational fun, making it an ideal spot for tourists and locals alike. Stoke Beach invites you to experience the pristine sands and crystal-clear waters of Florida's Gulf Coast. Whether you're looking to relax under the sun, take a refreshing swim, or enjoy a picturesque sunset, our beach provides the perfect backdrop for unforgettable moments.

Welcome to Madeira Beach Ticket Booth, your gateway to an unforgettable adventure in the heart of Florida's stunning Gulf Coast! Conveniently located at 15020 Madeira Way, Madeira Beach, Florida, our ticket booth is your one-stop destination for exploring the vibrant attractions and activities that Madeira Beach has to offer. As a premier tourist attraction, Madeira Beach Ticket Booth provides a wide array of tickets and packages tailored to suit every interest. Whether you're looking to embark on a thrilling dolphin-watching cruise, enjoy a relaxing sunset sail, or explore the local wildlife through eco-tours, we have something for everyone.

Welcome to Gulf Beach Realty, your trusted real estate agency nestled in the heart of Madeira Beach, Florida. Located at 203 150th Avenue, our agency is dedicated to providing exceptional real estate services to both buyers and sellers in the vibrant Gulf Beach community and beyond. At Gulf Beach Realty, we understand that finding the perfect home or investment property is a deeply personal journey. Our team of experienced and knowledgeable real estate professionals is committed to guiding you through every step of the process with personalized service and expert advice. Whether you are looking for a beachfront property, a cozy family home, or a lucrative investment opportunity, we have the local expertise and extensive listings to meet your unique needs.

Welcome to Tropical Beach Team Realtors, your premier real estate agency located in the heart of Madeira Beach, Florida. Nestled at 13443 Gulf Lane, our dedicated team is committed to helping you find your dream home or perfect investment property along the stunning Gulf Coast. At Tropical Beach Team Realtors, we specialize in connecting clients with the best residential and vacation properties in the Madeira Beach area. Our experienced agents possess in-depth local knowledge and a passion for the vibrant coastal lifestyle that defines this beautiful region. Whether you're buying, selling, or renting, we provide personalized service tailored to meet your unique needs and preferences.

Holiday Isles Resort is a popular Old Florida Style hotel located just across the street from the beach at 14711 Gulf Boulevard in Madeira Beach, Florida. Guests can choose from studio rooms with Gulf views or spacious 2 bedroom, 1 bathroom suites that offer the comforts of a condo. The pristine sand of Madeira Beach stretches from St. Pete to Clearwater, making it the perfect destination for a beach getaway. Only a 10-minute walk from John's Pass Village, guests can explore local shops, restaurants, and bars in the area. The hotel offers unique offers and discounts when booking through their website. Accepted forms of payment include Visa, MasterCard, Discover Card, Traveler's Checks, and cash.

Sunglow Seaside is a premier lodging, real estate, and travel agency located at 15468 Gulf Boulevard in Madeira Beach, Florida, United States. Our institution offers luxurious accommodations with stunning views of the Gulf of Mexico, as well as expert real estate services for those looking to invest in beachfront properties. Our dedicated travel agency also provides personalized vacation packages and concierge services to ensure a memorable stay on the beautiful Florida coast. Experience the ultimate seaside getaway at Sunglow Seaside.

Blue Hammock is a charming lodging institution located at 160 145th Avenue in the beautiful coastal town of Madeira Beach, Florida, United States. Nestled just steps away from the pristine white sand beaches and crystal clear waters of the Gulf of Mexico, Blue Hammock offers a relaxing and tranquil retreat for guests looking to unwind and rejuvenate. With comfortable accommodations, friendly staff, and convenient amenities, Blue Hammock is the perfect destination for a beach getaway. Whether you're looking to soak up the sun, explore the local shops and restaurants, or simply relax in a hammock by the water, Blue Hammock has everything you need for a memorable stay.

Sandy Shores Condominiums in Madeira Beach, Florida, offers newly furnished 1 and 2 bedroom vacation rentals with a casual and comfortable decor. These condos provide more features and value than a standard hotel room, including a full kitchen, living area, separate bedrooms, and a private balcony overlooking the white sandy beach and turquoise waters. Located next to the historic Johns Pass Fisherman’s Village and Boardwalk, guests have easy access to restaurants, shopping, water sports, and various vacation activities. Our onsite staff ensures that your stay is enjoyable and hassle-free, whether you are on a family vacation, honeymoon, or romantic getaway. John’s Pass Condos has been professionally managing vacation rental properties along the Gulf Coast since 1993, offering expert property management services for privately owned properties in the area. Experience the best of Madeira Beach at Sandy Shores Condominiums.

Charter Finders LLC. is a leading travel agency located at 15015 Madeira Way in beautiful Madeira Beach, Florida, United States. Specializing in yacht charters, fishing trips, and other luxury travel experiences, Charter Finders LLC. is dedicated to providing exceptional service and unforgettable adventures for their clients. Whether you're looking to explore the crystal-clear waters of the Gulf of Mexico or embark on a deep-sea fishing excursion, Charter Finders LLC. has the expertise and resources to make your dream vacation a reality. Contact them today to start planning your next unforgettable travel experience.

Welcome to Time Off Charters, your premier travel agency located in the heart of Madeira Beach, Florida. Nestled at 13111 Gulf Boulevard, we specialize in crafting unforgettable maritime adventures that cater to both locals and visitors seeking the ultimate escape. Our expert team is dedicated to providing personalized experiences, whether you're looking to embark on a serene sunset cruise, an exciting fishing trip, or a bespoke charter journey tailored to your desires. At Time Off Charters, we pride ourselves on our commitment to excellence and customer satisfaction. Our knowledgeable staff possesses extensive local expertise, ensuring that each excursion highlights the stunning beauty and unique charm of Florida's Gulf Coast. We offer a diverse fleet of well-maintained vessels, equipped with modern amenities to ensure a comfortable and enjoyable experience on the water.

Welcome to John's Pass Village Transit Station, your gateway to the vibrant and picturesque area of Madeira Beach, Florida. Conveniently located in the heart of John's Pass Village, our transit station provides seamless access to one of the most charming and bustling destinations along Florida's Gulf Coast. Whether you're a local resident or a visitor exploring the stunning beaches and lively boardwalk of Madeira Beach, our transit station is your ideal starting point. At John's Pass Village Transit Station, we prioritize comfort, efficiency, and accessibility to ensure a smooth travel experience. Our location offers easy connections to local attractions, dining, shopping, and entertainment options, making it the perfect hub for your adventures. With a commitment to safety and convenience, we strive to enhance your journey with well-maintained facilities and friendly service.

Welcome to Pinellas Coastal Home Search, your premier real estate agency conveniently located at 9180 Oakhurst Road, Seminole, Florida 33776. Nestled in the heart of the stunning Gulf Coast, our agency specializes in the vibrant communities of Pinellas County and beyond. Whether you're looking to buy, sell, or manage properties, our expert team is dedicated to making your real estate journey seamless and successful. Explore the charming towns and beautiful beaches that define this coastal paradise. From the tranquil shores of Belleair Beach to the lively atmosphere of Clearwater's downtown, there's something for everyone. Discover the historic charm of Dunedin, the serene sunsets in Madeira Beach, and the cultural richness of St. Petersburg. Our knowledgeable agents are here to guide you through every step of the process, ensuring that your interests are always our top priority.

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 Las Brisas Condominiums, your perfect getaway on the pristine shores of Madeira Beach, Florida. Nestled at 14710 Gulf Boulevard, our beachfront property offers a serene escape with breathtaking views of the Gulf of Mexico. Las Brisas Condominiums provides a unique blend of comfort and convenience, featuring spacious, well-appointed units that cater to families, couples, and solo travelers alike. Our accommodations boast modern amenities, including fully equipped kitchens, private balconies, and high-speed Wi-Fi, ensuring a relaxing and hassle-free stay. Guests can unwind by our sparkling outdoor pool, enjoy a barbecue at our communal grilling area, or take a leisurely stroll along the soft, sandy beach just steps from your door.