The 30 Best Florida vacation rentals in Madeira Beach, Florida

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Sea Breeze Condominiums is a luxurious real estate and travel agency located at 13500 Gulf Lane in Madeira Beach, Florida. Our stunning beachfront condos offer breathtaking views of the Gulf of Mexico and provide the perfect setting for a relaxing vacation or a permanent residence. With top-notch amenities and convenient access to the beach, shopping, and dining, Sea Breeze Condominiums is the ideal choice for those looking to experience the beauty of the Florida coast. Contact us today to learn more about our available properties and start planning your next 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.

Arie Dam Condominiums is a luxurious real estate agency and travel agency located at 14600 Gulf Boulevard in Madeira Beach, Florida. Our stunning beachfront condos offer breathtaking views of the Gulf of Mexico and provide a perfect getaway for those looking to relax and unwind. With top-notch amenities and exceptional customer service, Arie Dam Condominiums is the perfect destination for your next vacation or investment property. Experience the beauty of Madeira Beach with us!

PMI Clearwater, located at 801 West Bay Drive in Largo, Florida, offers top-notch full-service Short-Term Property Management for both guests and homeowners. As part of a reputable franchise with nearly 20 years of experience in the industry, PMI Clearwater ensures peace of mind for homeowners by treating their properties with care and maximizing profitability. With a focus on high-quality bookings and exceptional guest experiences, PMI Clearwater stands out from the competition with its dedication to hospitality management and full-time guest service. Our multi-channel marketing strategy reaches a wide range of vacation travelers, while our dedicated accounting department provides professional bookkeeping and financial practices for each property. We prioritize cleanliness and comfort for guests, implementing enhanced cleaning procedures and a certification program to ensure the highest standards of cleanliness in every room.

Tropic Breezes is a premier real estate and travel agency located at 14251 Gulf Boulevard in Madeira Beach, Florida, United States. Specializing in vacation rentals, property sales, and travel planning, Tropic Breezes offers a wide range of services to help clients find their dream beachfront property or plan the perfect getaway. With a team of experienced agents and travel experts, Tropic Breezes is dedicated to providing exceptional customer service and personalized assistance to make every client's experience seamless and enjoyable. Whether you're looking to buy or rent a property in the beautiful Gulf Coast region, or need help planning your next vacation, Tropic Breezes is the go-to destination for all your real estate and travel needs.

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.

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.

Located at 140 Boardwalk Place West in Madeira Beach, Florida, Shark Boat John's Pass is a popular tourist attraction and travel agency. One of the highlights of this institution is the Royal Conquest Ghost Ship, which cruises on weekends in October. Guests can party like it's 1666 on the Royal Conquest Pirate Ship, which sets sail up to 4 times daily. For a unique and thrilling experience, visitors can explore John's Pass's calm waterways inside the belly of a shark on the SHARK BOAT. Get up close and personal with the majestic Atlantic Bottlenose Dolphins as they swim and jump out of the water. Watch as the dolphins ride and play in the wake while taking in the beautiful sights of the Boca Ciega Bay in John's Pass Village.

Vtrips is a premier travel agency located in Madeira Beach, Florida, United States. Specializing in providing top-notch vacation rental properties, Vtrips offers a wide range of accommodations to suit every traveler's needs and preferences. Whether you're looking for a beachfront condo, a cozy cottage, or a luxurious villa, Vtrips has the perfect option for you. With excellent customer service and a dedication to creating unforgettable travel experiences, Vtrips is your go-to choice for planning your next vacation in Madeira Beach and beyond.

Sandbar Charters St. Pete is a premier travel agency located at 674 150th Avenue in Madeira Beach, Florida. Offering a range of exciting activities such as sandbars, dolphin watching, sunset cruises, swimming, shelling, exploring, dock and dine, and leisurely cruising, this institution is the perfect destination for those seeking a memorable and adventurous experience on the water. In addition to their regular offerings, Sandbar Charters St. Pete also provides custom charters, allowing guests to create their own personalized adventure. Don't miss out on the opportunity to explore the beautiful waters of Florida with Sandbar Charters St. Pete!

Hubbard's Marina is a well-known tourist attraction and travel agency located in Madeira Beach, Florida. Situated at 170 Boardwalk Place East, this institution offers a wide range of services for travelers looking to explore the beautiful waters of the Gulf Coast. From boat rentals and fishing charters to sunset cruises and dolphin watching tours, Hubbard's Marina provides unforgettable experiences for visitors of all ages. With a convenient location near the beach and a knowledgeable staff ready to assist with all your travel needs, Hubbard's Marina is the perfect destination for those looking to make the most of their time in Florida.

No Worries Sailing Adventures is a premier travel agency located in Madeira Beach, Florida. Our team of experienced professionals is dedicated to providing unforgettable sailing experiences for our clients. Whether you are looking for a relaxing sunset cruise, a thrilling snorkeling excursion, or a multi-day sailing adventure, we have a variety of options to choose from. Sit back, relax, and let us take care of all the details – with No Worries Sailing Adventures, your dream vacation is just a sail away. Visit us at 565 150th Avenue to start planning your next adventure today.

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.

Eagle Parasail is a premier travel agency located in Madeira Beach, Florida, United States. Specializing in parasailing adventures, Eagle Parasail offers thrill-seekers the opportunity to soar high above the stunning waters of the Gulf of Mexico. With top-of-the-line equipment and experienced guides, guests can feel safe and secure as they experience the exhilarating feeling of flying like an eagle. Whether you're a first-time parasailer or a seasoned pro, Eagle Parasail provides an unforgettable experience for all. Book your adventure today and make memories that will last a lifetime.

Welcome to John's Pass Plaza, LLC, your premier parking destination located at 179 Boardwalk Place East, Madeira Beach, Florida. Nestled in the heart of the vibrant John's Pass Village, our convenient parking facility offers easy access to the stunning beaches, eclectic shops, and diverse dining options that make this area a must-visit destination. Whether you're here for a day at the beach, a fishing adventure, or exploring the local attractions, John's Pass Plaza provides a safe, affordable, and accessible parking solution to meet your needs. Our well-maintained lot is just steps away from the action, ensuring you spend more time enjoying the sights and less time searching for parking. Experience the convenience and peace of mind that comes with parking at John's Pass Plaza, LLC. Visit us today and start your adventure in Madeira Beach hassle-free!

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 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 Blake Nieswand Real Estate & Property Management, your trusted partner in navigating the vibrant real estate market of Madeira Beach, Florida. Conveniently located at 15023 Gulf Boulevard, our agency is dedicated to providing unparalleled service to both buyers and sellers in the area. With a deep understanding of the local market and a commitment to excellence, we offer comprehensive real estate solutions tailored to meet your unique needs. Whether you're looking to buy your dream beachfront property, sell your home, or require expert property management services, our experienced team is here to guide you every step of the way. Discover the difference of personalized service and expert knowledge with Blake Nieswand Real Estate & Property Management, where your real estate goals become a reality. Contact us today to begin your journey in the beautiful Madeira Beach area.

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.

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!