TOP 30 Gulf of mexico vacation rentals in Anna Maria, Florida

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The Anna Maria Island Inn is a charming lodging establishment located at 2200 Gulf Drive North in Bradenton Beach, Florida. Situated on the beautiful Anna Maria Island, this inn offers guests a peaceful and relaxing getaway just steps away from the Gulf of Mexico. The inn features comfortable accommodations, stunning ocean views, and convenient access to the island's attractions and activities. Whether you're looking for a romantic retreat, a family vacation, or a solo adventure, the Anna Maria Island Inn is the perfect choice for your stay in Florida.

Anna Maria Beach Resort is a charming lodging located at 6306 Gulf Drive in Holmes Beach, Florida. This beachfront resort offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With stunning views of the Gulf of Mexico, guests can unwind in comfortable accommodations and enjoy the natural beauty of Anna Maria Island. The resort's convenient location allows for easy access to nearby attractions, restaurants, and activities, making it the perfect destination for a memorable beach vacation. Whether you're looking to soak up the sun on the sandy shores or explore the island's quaint shops and galleries, Anna Maria Beach Resort provides the ideal setting for a truly unforgettable getaway.

Playa Anna Maria in Florida is a charming tourist attraction located at 407 North Bay Boulevard in Anna Maria. This beautiful beach destination offers stunning views of the Gulf of Mexico, soft sandy shores, and crystal-clear waters perfect for swimming and sunbathing. Visitors can relax under the shade of palm trees, take a leisurely stroll along the shoreline, or enjoy water activities such as paddleboarding and kayaking. Playa Anna Maria is a must-visit destination for those looking to unwind and soak up the sun in a picturesque setting.

The Beach Club at Anna Maria by RVA is a luxurious beachfront lodging destination located at 2201 Gulf Drive North in Bradenton Beach, Florida. This institution offers a variety of rental properties including condos, villas, and private homes, perfect for a relaxing vacation or a romantic getaway. With stunning views of the Gulf of Mexico, guests can enjoy direct beach access, a heated pool, and a variety of amenities to enhance their stay. Whether you are looking for a weekend retreat or a longer stay, The Beach Club at Anna Maria by RVA is the perfect choice for your next beach vacation. Contact their real estate and travel agency to book your stay today.

Birds Nest Apartments on Anna Maria Island is a charming vacation rental located at 403 Gulf Drive South in Bradenton Beach, Florida. This cozy lodging option offers a peaceful retreat for guests looking to unwind and relax in a beautiful beachfront setting. The apartments are well-appointed and feature all the amenities needed for a comfortable stay, including fully equipped kitchens, spacious living areas, and private balconies with stunning views of the Gulf of Mexico. With its convenient location near the beach and various attractions, Birds Nest Apartments is the perfect choice for a memorable getaway on Anna Maria Island.

Beach Boutique Rentals, located at 208 Pine Avenue in Anna Maria, Florida, is a real estate and travel agency specializing in vacation rentals on the beautiful Anna Maria Island. With seven miles of stunning white sand beaches and breathtaking sunsets over the Gulf of Mexico, the island truly is a paradise. At Beach Boutique Rentals, we offer a range of vacation rentals including scenic view condos, charming cottages, and luxury homes. Some of our rentals are dog-friendly, so you can bring your furry friends along for the trip. Whether you prefer a direct Gulf front condo or a multi-family villa, we have the perfect place for your dream vacation.

Harbor Lane Court offers luxurious vacation rentals on the beautiful Anna Maria Island in Florida. Located at 4509 Gulf Drive in Holmes Beach, this lodging institution provides guests with a serene and comfortable stay just steps away from the stunning Gulf of Mexico. Enjoy spacious accommodations, modern amenities, and a prime location for exploring the island's charming shops, restaurants, and attractions. Immerse yourself in the laid-back island lifestyle and create unforgettable memories at Harbor Lane Court.

Island Real Estate of Anna Maria Island, Inc. is a premier real estate and travel agency located at 6101 Marina Drive, Holmes Beach, Florida, United States. Specializing in vacation rentals on the beautiful Anna Maria Island, our agency offers a wide range of beachfront properties with stunning views of the Gulf of Mexico. With over 50 years of experience, our dedicated staff is committed to providing top-notch customer service and ensuring that every guest has a relaxing and memorable stay. From cozy beachfront cottages to luxurious oceanfront mansions, we have the perfect rental for every taste and budget. Our team of local experts are available 24/7 to assist with any questions or concerns, and can provide recommendations for the best local spots and experiences to enjoy during your stay. Whether you're looking for a quick getaway or a long-term investment, Island Real Estate has you covered. Book your Anna Maria Island rental today and experience the beauty and charm of Florida's hidden gem.

Anna Maria Beach Cottages is a charming real estate and travel agency located at 112 Oak Avenue in Anna Maria, Florida. Our cottages are nestled in a picturesque beachfront location, offering guests a cozy and comfortable retreat for their vacation. With a variety of accommodations to choose from, including beachfront cottages and villas, guests can enjoy stunning views of the Gulf of Mexico and easy access to the beautiful sandy beaches. Our dedicated team is committed to providing exceptional service and ensuring that every guest has a memorable and relaxing stay. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Anna Maria Beach Cottages is the perfect destination for your next beach escape.

Pelican Bay Vacation Rental Home is a charming and spacious accommodation located in Anna Maria, Florida, United States. This beautiful home offers guests a relaxing and comfortable stay with all the amenities needed for a perfect vacation. With a prime location just a short walk from the beach, guests can enjoy stunning views of the Gulf of Mexico and easy access to the sand and surf. The home features modern furnishings, a fully equipped kitchen, and a private pool for guests to enjoy. Whether you're looking for a family getaway or a romantic retreat, Pelican Bay Vacation Rental Home is the perfect place to relax and unwind in Anna Maria.

Mermaids Crossing Beach Vacation Rental on Anna Maria Island in Florida offers stunning vacation rental properties for visitors looking to enjoy a relaxing beach getaway. Situated at 207B 69th Street in Holmes Beach, this real estate and travel agency specializes in providing luxurious accommodations with breathtaking views of the Gulf of Mexico. Whether you're seeking a romantic escape or a fun-filled family vacation, Mermaids Crossing has the perfect rental for you. Experience the beauty of Anna Maria Island and make unforgettable memories at Mermaids Crossing Beach Vacation Rental.

Cortez Florida Vacations is a charming lodging institution located in the historic Cortez fishing village at 4507 125th Street West, Bradenton, Florida. Situated just over the bridge from Anna Maria Island, this waterfront property offers a tranquil escape with five beautifully restored 1936 cottages. Each cottage features modern amenities while maintaining its original charm, including fully equipped kitchens, televisions, Wi-Fi, and antique doors. Guests can relax in the private Courtyard, enjoy views of the bay, or host events in the 1,000 square-foot Boathouse event space. The property can accommodate up to 32 overnight guests and offers venue packages for up to 150 guests. Shopping, dining, museums, spas, and the famous white sand beaches of Anna Maria Island are all within walking or biking distance. Owners Heidi and John Banyas created Cortez Florida Vacations after designing their own fairytale wedding space in the village. They aim to provide excellent service and help guests create lasting memories in this piece of old Florida paradise. Whether you're looking for a quiet getaway or a venue for a special event, Cortez Florida Vacations has something for everyone.

Anna Maria Beach Vacations is a real estate and travel agency located at 787 North Shore Drive in Anna Maria, Florida, United States. Experience stunning sunsets and breathtaking views of the Gulf of Mexico from every room in this three-bedroom, two-bath ground level home. Handicap accessible with walk-in showers and no stairs to climb, this home offers easy access for all. Just four blocks from the Gulf Beach and two blocks from Tampa Bay Beach, this lovely island pool house features a mix of newer furnishings and vintage pieces. The kitchen is equipped with a coffee maker, microwave, and dishwasher. Situated directly at the water's edge in Northern Anna Maria Island, this beautiful 3 bedroom 2.5 bath home offers unforgettable views of Manatees and Dolphins playing in the crystal blue waters of Tampa Bay. All rentals are subject to 5.5% sales tax, 6.5% Manatee county tax, as well as cleaning and maintenance fees. Guests have praised their experience at Anna Maria Beach Vacations, mentioning the cleanliness, comfort, and fully stocked amenities of the home. The location on the island is perfect for relaxing and enjoying the beautiful surroundings. Whether watching the surf, sunsets, or lightning storms over the Gulf, guests have found their stay to be a wonderful and memorable experience.

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.

MI Happy Place Island Resort is a charming lodging located at 301 42nd Street, Holmes Beach, Florida, United States. Our resort offers a full size pool that is heated and chilled as needed to ensure a great vacation experience. Whether you are planning a family reunion, a romantic beach wedding, a corporate function, or just a fun getaway, our resort is the ideal setting for all occasions. The recently renovated and remodeled units at MI Happy Place Island Resort offer casual elegance and a beachy, fun decor that welcomes you to relax in style. Each unit comes with a full kitchen, luxurious bath linens, and incredibly comfortable beds. You can choose to spend your days lounging by the pool and having a barbecue, both of which are included with your stay.

Located at 2710 Gulf Drive North in Holmes Beach, Florida, Cedar Cove Resort & Cottages offers a perfect blend of boutique beachfront luxury and classic "Old Florida" charm. Surrounded by lush coconut palms and vibrant orchids, this resort provides a tranquil setting for guests to relax and unwind. With 19 unique beachside suites, studios, and Key West-style cottages, each offering modern amenities and services, guests can truly embrace the laid-back island lifestyle. Guests rave about the friendly staff, pristine private beach, and convenient access to local restaurants and shops. The resort's location on Anna Maria Island allows for easy exploration of the seven miles of sun-kissed sand and turquoise waters along the Gulf of Mexico. The Anna Maria Island Trolley offers free transportation around the island, making it simple for guests to discover all that this beautiful destination has to offer.

Bay Breeze Cottages is a charming lodging institution located at 617 North Bay Boulevard in Anna Maria, Florida. Nestled in the heart of this picturesque coastal town, the cottages offer a peaceful retreat just steps away from the stunning beaches of the Gulf of Mexico. Guests can enjoy cozy accommodations with modern amenities, a private patio or balcony, and access to a sparkling outdoor pool. Whether you're looking for a romantic getaway or a fun-filled family vacation, Bay Breeze Cottages provides the perfect setting for a memorable stay in beautiful Anna Maria.

Palmetto Ave Beach is a serene park located at 100 Palmetto Avenue in Anna Maria, Florida. This beautiful beachfront destination offers stunning views of the Gulf of Mexico and white sandy shores perfect for sunbathing and picnicking. Visitors can enjoy a relaxing day by the water, swim in the crystal-clear ocean, or take a leisurely stroll along the shore. The park also features amenities such as restrooms, picnic tables, and shaded areas for a comfortable day out in the sun. Whether you're looking to unwind with a book or have a fun day with family and friends, Palmetto Ave Beach is the ideal spot for a peaceful beach day in Florida.

Villa #3 Seahorse is a charming lodging establishment located at 3605 Gulf Drive in Holmes Beach, Florida, United States. This cozy villa offers a relaxing tropical atmosphere with stunning views of the Gulf of Mexico. Guests can enjoy a peaceful getaway with easy access to the beach, as well as nearby dining and shopping options. The villa features comfortable accommodations, a fully equipped kitchen, and a private outdoor patio for guests to unwind and soak up the sunshine. Whether you're looking for a romantic retreat or a family vacation, Villa #3 Seahorse is the perfect destination for a memorable stay on Anna Maria Island.

Nautilus Condominiums is a luxurious real estate and travel agency located at 7100 Gulf Drive in Holmes Beach, Florida, United States. Our stunning beachfront condos offer breathtaking views of the Gulf of Mexico and provide the perfect setting for a relaxing vacation or a permanent home. With top-notch amenities and a prime location, Nautilus Condominiums is the ideal choice for those looking to experience the beauty and tranquility of Anna Maria Island. Contact us today to learn more about our available properties and start planning your next getaway in paradise.

Laplage 9 is a luxurious beachfront vacation rental located at 6426 Gulf Drive in Holmes Beach, Florida. This stunning property offers guests a serene and stylish retreat with breathtaking views of the Gulf of Mexico. With spacious accommodations, modern amenities, and a prime location just steps from the sandy shores, Laplage 9 is the perfect destination for a relaxing getaway on Anna Maria Island. Whether you're looking to soak up the sun, explore the local attractions, or simply unwind in paradise, Laplage 9 has everything you need for a memorable vacation experience.

Runaway Bay Condominium Association is located on the beautiful Anna Maria Island in Bradenton Beach, Florida. With 186 one- and two-bedroom units, our award-winning complex offers a premier island paradise experience. Nestled between Palma Sola Bay and the Gulf of Mexico, Runaway Bay features a fishing pier, private beach access, and six miles of pristine sandy beaches. Our modern condominiums are surrounded by lush tropical landscaping, lagoons, and fountains, creating a tranquil environment. Guests can enjoy the largest heated swimming pool on the island, a tennis/pickleball court, fitness room, sauna, clubhouse, Bocce ball court, shuffleboard court, and outdoor grills. The complex is conveniently located near dining options, historic Bridge Street, fishing spots, bike paths, shops, and golf courses.

Dans Florida Condos, LLC is a real estate and travel agency located at 1801 Gulf Drive North in Bradenton Beach, Florida, United States. Our charming vacation rental homes offer private beach access just steps away from the Gulf of Mexico. With two bedroom and two bath or one bedroom and one bath options, these condos are situated in the heart of Anna Maria within the Runaway Bay Condominium Community. Enjoy easy access to Historic Bridge Street, restaurants, coffee shops, bars, shopping boutiques, and miniature golf. Take a short walk to Anna Maria's own Golf Course or explore other courses along the coast. Pirate City, the Spring Training Headquarters of the Pittsburgh Pirates, is also nearby. Come stay with us at Dan's Florida Condos for a memorable beach vacation experience.

Palm Isle Village Resort is a luxurious real estate and travel agency located at 3201 Gulf Drive in Holmes Beach, Florida, United States. Our resort offers exquisite vacation rentals and properties for sale in the heart of Anna Maria Island. With stunning views of the Gulf of Mexico, our resort provides a peaceful and relaxing escape for travelers looking for a tropical paradise. Our dedicated team of professionals is committed to providing top-notch service and ensuring that every guest has a memorable stay. Whether you are looking for a short-term vacation rental or a permanent residence, Palm Isle Village Resort has the perfect property for you. Experience the beauty of Anna Maria Island with us today!

SailingAMI is a travel agency located at 12312 Manatee Avenue West in Bradenton, Florida, United States. Embark on a daily sightseeing sailing adventure aboard a classic 1972 35 ft. Bristol Yawl. This beautiful vessel offers up to 4 sails for a smooth cruising experience on Anna Maria Sound and the Gulf of Mexico. Enjoy stunning views of Anna Maria Island's beaches, mangrove islands, water birds, manatees, dolphins, turtles, and more. For more information on times, location, and pricing, please call (941)713-8000.

Happy Paddler Kayak Tours & EcoVentures is a family-owned travel agency located at 6844 Gulf of Mexico Drive in Longboat Key, Florida. Our team of water-loving naturalists and paddling instructors are dedicated to exploring and educating others about our watery world. We offer kayak and paddleboard rentals, as well as award-winning tours around Anna Maria Island, Longboat Key, Lido Key, and Sarasota. Join us for a Coastal Island Tour where you can kayak with manatees, dolphins, and a variety of ocean life. Explore the mangrove tunnels at Lido Key, a popular destination for families. Experience the stunning Florida Gulf Coast sunsets on our Sunset Kayak Tour. Or rent a kayak or paddleboard for a half-day and chart your own course through the crystal clear waters of Longboat Pass.

Welcome to Between The Tides, your premier destination for real estate and travel experiences in the heart of Florida's Gulf Coast. Nestled at 3721 116th Street West, Bradenton, Florida, our unique agency offers a blend of accommodation and adventure, perfect for those looking to explore the stunning beauty of Anna Maria Island, Bradenton, and the historic charm of Cortez. Discover the allure of coastal living with our charming 1 Bed/1 Bath property, thoughtfully designed to provide both comfort and convenience. With a Queen bed, Sofa Sleeper, child-size bunks, and a futon in the Lanai, this cozy retreat accommodates up to six guests. Enjoy the open layout with a work/desk area, a fully equipped kitchen, and a spacious Lanai that extends to a breezy back patio, creating a perfect space for relaxation.

Welcome to Villa #1 Sailfish by AMI Locals, your perfect getaway on beautiful Anna Maria Island. Nestled at 3605 Gulf Drive, Holmes Beach, Florida, this charming two-bedroom, two-bath villa is a mere two-minute stroll from the pristine Gulf of Mexico beaches. Part of the picturesque Island West Resort, Villa #1 Sailfish offers a delightful blend of comfort and convenience, ideal for families, couples, and friends traveling together. Highlights of Villa #1 Sailfish include: