TOP 10 Vacation rentals and stays in Madeira Beach, Florida

Vicinity Vacation Rentals is a premier real estate and travel agency located at 14225 Gulf Boulevard in Madeira Beach, Florida. We specialize in offering luxurious vacation rental properties in the beautiful coastal region of Florida. Our dedicated team of professionals is committed to providing top-notch service and ensuring that our guests have a memorable and enjoyable stay. Whether you are looking for a beachfront villa, a cozy cottage, or a spacious condo, we have the perfect accommodation for your vacation needs. Contact us today to book your dream getaway in sunny Florida!

Prime Waters at the Cambria Madeira Beach is a waterfront hotel located at 15015 Madeira Way in Madeira Beach, Florida, United States. This institution offers a refined and relaxed stay, encouraging guests to unwind and enjoy the beautiful surroundings. With a marina on-site and just a short distance from the beach, guests can easily explore the area by land or sea. The rooftop infinity pool and bar provide stunning views of the sunset, perfect for sipping cocktails and taking in the scenery. The fully equipped gym, elevated courtyard, and free Wi-Fi offer additional amenities for guests to enjoy. The hotel's restaurant, Prime Waters, serves locally sourced dishes in a relaxed setting, while the rooftop bar, Ember, offers refreshing drinks and breathtaking sunsets.

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.

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.

Commodore Beach Club Condo is a luxurious lodging institution situated at 13536 Gulf Boulevard in Madeira Beach, Florida, United States. This beachfront property offers stunning views of the Gulf of Mexico and provides guests with a comfortable and relaxing stay. The condos are spacious and well-appointed, with modern amenities and stylish decor. Guests can enjoy the outdoor pool, hot tub, and direct access to the beach. Whether you're looking for a romantic getaway or a fun family vacation, Commodore Beach Club Condo is the perfect choice for your stay in Madeira Beach.

All Seasons Vacation Resort is a premier lodging destination and real estate agency located at 13070 Gulf Lane in Madeira Beach, Florida. Nestled along the beautiful Gulf Coast, this resort offers a variety of accommodations for guests looking to relax and unwind in paradise. Whether you're searching for a cozy beachfront condo or a luxurious vacation home, All Seasons Vacation Resort has something for everyone. With stunning views, top-notch amenities, and a prime location near the area's best attractions, this resort is the perfect choice for your next getaway. Book your stay today and experience the best of Madeira Beach at All Seasons Vacation Resort.

Welcome to Madeira Bay Resort unit 305, a luxurious lodging option located at 13235 Gulf Boulevard in Madeira Beach, Florida, United States. This upgraded one bedroom plus den condo offers a stunning view of Boca Ciega Bay and the Marina, right in the heart of Madeira Beach. Enjoy the on-site full service Spa and Restaurant, as well as the beautifully furnished interior with new flooring, granite countertops, and stainless appliances. Relax on the private balcony and take in the picturesque marina and bay views. The master suite features a luxurious King-size bed, while the 2nd bedroom/den has two twin size beds and there is a Queen size sleep sofa in the living room.

Madeira Beach C Star5Vacations is a luxurious lodging institution located at 14785 North Bayshore Drive in Madeira Beach, Florida, United States. With stunning views of the bay and top-notch amenities, this institution offers a truly unforgettable vacation experience. Whether you're looking for a romantic getaway or a family-friendly retreat, Madeira Beach C Star5Vacations has everything you need for a comfortable and enjoyable stay. Book your stay today and experience the beauty of Madeira Beach in style.

The Cottages at Madeira Beach is a charming and cozy lodging option located at 13302 1st Street East in Madeira Beach, Florida. This institution offers a unique blend of comfort and convenience, making it the perfect choice for travelers looking for a relaxing getaway. Whether you're looking to rent a cottage for a weekend retreat or interested in purchasing a vacation home, The Cottages at Madeira Beach has you covered. With a prime location near the beach and a range of amenities, this institution is sure to provide an unforgettable experience for guests. Book your stay or inquire about real estate options today with The Cottages at Madeira Beach.

Madeira Beach Cottages is a charming lodging option located at 13200 Gulf Boulevard in Madeira Beach, Florida. This institution offers cozy and well-appointed cottages for visitors looking for a relaxing getaway by the beach. As a real estate agency, Madeira Beach Cottages also assists guests in finding their dream vacation home in this picturesque coastal town. Additionally, as a travel agency, they provide personalized travel itineraries and recommendations to ensure a memorable and enjoyable stay in Madeira Beach. Whether you are looking for a short-term rental or a permanent residence, Madeira Beach Cottages has you covered with their excellent services and accommodations.

Welcome to John's Pass Fisherman's Cove & Cottages vacation rentals, situated at 12989 Pelican Lane in Madeira Beach, Florida. Just steps away from the famous Johns Pass Village, our waterfront cottages offer the perfect beach getaway for families and friends. With easy access to the beach, boardwalk, shops, and restaurants, there is never a dull moment during your stay. Relax by the intercostal waterways with a drink in hand after a day of sun-soaked fun. Book your stay with us on VRBO for a memorable experience in Madeira Beach.

BeachesUSA Vacation Rentals and Management is a real estate and travel agency located at 14321 Walsingham Road, Largo, Florida, United States. With over 230 vacation rentals to choose from, this institution offers the perfect accommodations for your beach getaway. Located in a charming beachfront town, this institution offers properties in a destination that has been ranked as one of the Best Beaches in the USA and top 6 in the world by TripAdvisor. Enjoy the white sandy beaches and a variety of attractions suitable for visitors of all ages. Don't miss out on visiting Pier 60 during your stay.

Madeira Vista Condos is a real estate and travel agency located at 14800 Gulf Boulevard in Madeira Beach, Florida, United States. We offer beautiful condos with stunning views of the beach, available for rent in April and May. Our location provides unobstructed views up and down the beach, making us the closest to the water compared to other condos in the area. Our on-site management team is available to assist with any issues that may arise during your stay, ensuring a comfortable and enjoyable experience. We are proud to be ranked #1 on Trip Advisor, showcasing our dedication to customer satisfaction.

Distinctive Beach Rentals in St Pete / Clearwater is a premier real estate and travel agency located at 14995 Gulf Boulevard in Madeira Beach, Florida. We specialize in providing luxurious and unique beachfront vacation rentals for visitors looking to experience the beauty and relaxation of St Pete and Clearwater. Our team of experts is dedicated to helping guests find the perfect rental property that suits their needs and preferences. Whether you're looking for a cozy beachfront condo or a spacious vacation home, we have a wide selection of properties to choose from. Trust Distinctive Beach Rentals to make your stay in St Pete / Clearwater unforgettable.

Seaview Vacations in Madeira Beach, Florida is the ideal destination for beach lovers looking for a memorable getaway. Our beachfront condos offer stunning views of the Gulf of Mexico, with 2 and 3 bedrooms to accommodate your needs. With easy check-ins and convenient amenities, including a heated pool and hot tub, you can start relaxing as soon as you arrive. Whether you want to soak up the sun, explore the local scene, or simply unwind by the ocean, Seaview Vacations has everything you need for a perfect beach vacation. Book your stay today and experience the luxurious beachfront living at Seaview Vacations!

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.

Blue Water House Rentals is a premier lodging institution located at 13337 Gulf Boulevard in Madeira Beach, Florida. Situated in the heart of this beautiful beach town, our rentals offer guests a luxurious and comfortable stay just steps away from the sandy shores of the Gulf of Mexico. With a variety of rental options to choose from, including beachfront villas and cozy cottages, Blue Water House Rentals is the perfect choice for a relaxing getaway. Our friendly staff is dedicated to providing top-notch service and ensuring that each guest has a memorable and enjoyable stay. Experience the best of Madeira Beach at Blue Water House Rentals.

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.

Starfish Apartments & Cottages is a charming lodging institution located directly on the beautiful Madeira Beach in Florida. The historic property, over 80 years old, has been lovingly maintained and updated by the same family for over 40 years. With a variety of amenities including cable TV, high-speed internet, and a beachfront location, guests can enjoy a comfortable and relaxing stay. The property manager, SunBeach Properties, is always available to assist with any needs or inquiries. Whether it's your first visit or you're a returning guest, Starfish Apartments & Cottages aims to provide an excellent experience for all.

Surf Song Resort Condominiums is a charming beachfront lodging option located at 12960 Gulf Boulevard in Madeira Beach, Florida. This institution offers spacious and well-appointed condominiums for visitors looking for a comfortable and convenient stay. Whether you are looking for a vacation rental, a real estate investment, or assistance with travel arrangements, Surf Song Resort Condominiums has you covered. Enjoy stunning views of the Gulf of Mexico, easy access to the beach, and a range of amenities to make your stay enjoyable. Experience the beauty of the Florida coast at Surf Song Resort Condominiums.

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.

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.

Judy's Tropical Cottages is a charming lodging establishment located at 13136 4th Street East, Madeira Beach, Florida, United States. Nestled in a tropical paradise, this cozy retreat offers guests a relaxing and peaceful stay just steps away from the beautiful beaches of the Gulf Coast. Each cottage is tastefully decorated in a tropical theme and equipped with all the amenities needed for a comfortable stay. Whether you're looking for a romantic getaway or a fun family vacation, Judy's Tropical Cottages is the perfect choice for your next trip to Madeira Beach.

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.

Collwood Condos is a premier real estate and travel agency located at 13440 Gulf Lane in beautiful Madeira Beach, Florida. Our agency specializes in providing luxurious and comfortable condominiums for both short-term vacation rentals and long-term stays. With stunning views of the Gulf of Mexico and easy access to the beach, Collwood Condos offers the perfect combination of relaxation and convenience for all of our guests. Whether you're looking for a weekend getaway or a new permanent residence, our experienced team is dedicated to helping you find the perfect property to suit your needs. Contact us today to start planning your next unforgettable stay at Collwood Condos.

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.

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.

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!