TOP 30 Florida keys vacations in Anna Maria, Florida

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.

The Anna Maria Motel Resort is a charming lodging option located at 808 North Bay Boulevard in Anna Maria, Florida. This quaint resort offers comfortable accommodations in a picturesque setting, perfect for those looking to relax and unwind in the Sunshine State. With easy access to the beach and nearby attractions, guests can enjoy a peaceful and rejuvenating stay at this lovely resort. Experience the laid-back atmosphere and warm hospitality of Anna Maria Motel Resort during your next getaway to Florida.

Rent The Keys is a lodging, real estate, and travel agency located at 3018 Gulf Drive in Holmes Beach, Florida. Start your vacation now by booking Florida Keys luxury vacation rentals through RentTheKeys.com. Discover the value and savings of staying in vacation rental homes or condominiums with amenities such as heated pools, gourmet kitchens, and custom-designed properties on the best beaches in the world. Explore the various keys on the Gulf Coast of Florida, including Siesta Key, Anna Maria Island, Lido Key, Longboat Key, and Casey Key. Experience island living on Anna Maria Island and Siesta Key with miles of white sandy shores and crystal-clear waters. RentTheKeys also offers Sarasota Florida Keys vacation rentals.

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.

Mike Norman Realty on Anna Maria Island is a reputable real estate and travel agency located at 3101 Gulf Drive in Holmes Beach, Florida. Specializing in vacation rentals, property sales, and property management services, this institution is dedicated to helping clients find their perfect slice of paradise on the stunning Anna Maria Island. With a team of experienced agents and a deep knowledge of the local market, Mike Norman Realty offers personalized assistance and top-notch customer service. Whether you are looking to buy, sell, or rent a property on Anna Maria Island, this agency is your go-to destination for all your real estate needs.

Anna Maria Yacht Charters LLC is a premier travel agency located at 4208 129th Street West, Cortez, Florida, United States. Known as the region's most reliable and fun boat charters, they offer an unforgettable experience cruising the waters from Anna Maria Island to Sarasota Bay. With a maximum capacity of 6 passengers, their yacht certified boat provides ample room and comfortable seating for guests to enjoy a variety of activities. From dolphin tours with occasional manatee sightings to island hopping adventures, Anna Maria Yacht Charters LLC offers a customizable experience tailored to enhance your time on the water. Guests can enjoy snorkeling at Egmont Key, exploring Passage Key's pristine waters, and relaxing on the beautiful beaches of Jew Fish Key.

Florida Sail in St. Petersburg, FL, offers exclusive private sail charters for those looking to experience the beauty of the water in a personalized way. Located at 400 Treasure Island Causeway in Treasure Island, Florida, this travel agency provides worry-free packages that include everything you need for a day of sailing and exploration. From snorkeling in crystal-clear waters to relaxing on pristine beaches, Florida Sail offers customizable day sails that cater to your preferences. With experienced captains, fuel, docking, snorkels, snacks, and beverages all included, you can enjoy a seamless sailing experience while taking in the sights of the bay and potentially spotting wild dolphins.

Welcome to Anna Maria General Store, your one-stop destination for all your needs on beautiful Anna Maria Island. Nestled at 307 Pine Avenue, Anna Maria, Florida, our charming store offers a delightful blend of convenience and local charm. Whether you're a resident or a visitor, you'll find an array of essentials and unique finds to enhance your island experience. Our store proudly stocks a wide selection of groceries, fresh produce, and everyday essentials to keep your pantry well-stocked. We also feature a curated collection of locally-made products, souvenirs, and beach accessories, making it easy to find the perfect memento of your time on the island.

Welcome to Coconut Rentals - Golf Cart Rentals Anna Maria Island, your premier destination for exploring the beautiful Anna Maria Island with ease and style. Conveniently located at 5338 Gulf Drive, Holmes Beach, Florida, our business offers a unique blend of car rental services and local charm, making us a must-visit attraction for both tourists and residents alike. At Coconut Rentals, we specialize in providing top-quality golf cart rentals, perfect for navigating the island's scenic roads and discovering its hidden gems. Our fleet of modern and well-maintained golf carts ensures a comfortable and enjoyable ride, allowing you to soak in the breathtaking coastal views and vibrant island life.

Welcome to Anna Maria Beach Store, your one-stop destination for all your beach essentials and more! Conveniently located at 99 Spring Avenue in the heart of Anna Maria, Florida, our store offers a delightful shopping experience for both locals and visitors alike. Discover a wide array of high-quality beachwear, accessories, and unique souvenirs that capture the essence of our beautiful coastal town. Whether you're looking for stylish swimwear, comfortable flip-flops, or that perfect memento to remember your trip, Anna Maria Beach Store has something for everyone. Stop by today and let our friendly staff help you find exactly what you need for a perfect day at the beach. We look forward to serving you at Anna Maria Beach Store, where sunshine and smiles are always in stock!

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.

Welcome to Anna Maria Boat Company, your premier travel agency located at 12300 Manatee Avenue West, Bradenton, Florida. Nestled in the heart of the stunning Gulf Coast, we specialize in creating unforgettable aquatic adventures and bespoke travel experiences tailored to your desires. Whether you're seeking a serene day on the water, an exhilarating fishing expedition, or a unique island-hopping journey, our dedicated team is here to craft the perfect itinerary for you. With a passion for the sea and a commitment to exceptional service, Anna Maria Boat Company promises an unparalleled escape into the natural beauty of Florida's waterways. Discover the magic of the sea with us today!

Welcome to Coastal Key Realty, your premier real estate agency located at 6750 Gulf of Mexico Drive, Longboat Key, Florida. As a leading realtor in the vibrant areas of Anna Maria Island and Longboat Key, Amy Jones and her dedicated team are committed to providing personalized service and expert guidance for all your real estate needs. Whether you are looking to buy, sell, or invest, Coastal Key Realty offers the experience and expertise necessary to navigate the dynamic Florida real estate market. Our website showcases a diverse range of listings, each offering unique opportunities to find your perfect vacation home or permanent residence. From the picturesque community of Cedars Longboat Key to the luxurious Key Royale golf community on Anna Maria Island, we provide comprehensive guides to help you make informed decisions.

Located on Pine Avenue in Anna Maria, Florida, AMI Beach & Dog Supply is a pet store that offers a wide range of products for your furry friends. From frozen treats to beach gear, we have everything your dog could need. We also carry dog-themed items for dog lovers and professionals, including gear for service and working canines. You can shop online or visit our store for pickup or free delivery on Anna Maria Island and Longboat Key. We are dedicated to supporting professional canine groups and offer fundraising initiatives to help fund equipment and training. Stop by with your pup and say hello - we love meeting new furry friends!

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.

ABC Baby and Beach Equipment Rentals is a premier rental service located at 2239 15th Street in Sarasota, Florida. We specialize in providing high-quality baby supplies and beach gear for rent in Sarasota, Siesta Key, Lakewood Ranch, Anna Maria Island, and Bradenton. Our delivery and pick-up process is convenient and hassle-free, with deliveries made before standard check-in times and returns scheduled after check-out. We offer free delivery on orders over $150 to most zip codes, with no additional service charges.

Captain Fin's Sightseeing and Boat Tours is a popular tourist attraction and travel agency located at 1325 Gulf Drive South in Bradenton Beach, Florida, United States. Specializing in sunset cruises, dolphin excursions, sandbar trips, shelling adventures, and Egmont Key charters, Captain Fin's offers a unique way to explore the beautiful intercoastal waterways of Anna Maria, Longboat Key, and Sarasota Bay. With over 45 years of experience on the waters of Anna Maria Island and Tampa Bay, Captain Fin's ensures a memorable and enjoyable experience for all guests. Don't miss the opportunity to relax and watch the stunning sunset while sipping on your favorite beverage, or to collect shells along the secluded beaches of Egmont Key. Book your sightseeing and boat tour with Captain Fin's today for an unforgettable adventure on the waters of Florida's Gulf Coast.

ABC Baby and Beach Equipment Rentals is a clothing store located at 5700 Midnight Pass Road in Siesta Key, Florida. We specialize in providing baby and beach gear rentals for families visiting Sarasota, Siesta Key, Lakewood Ranch, Anna Maria Island, and Bradenton. Our delivery and pick-up process is convenient and easy, with deliveries made before standard check-in times and returns done after check-out. We offer free delivery on orders over $150 in most zip codes, with no service charges.

Pirate Monkey Boat Rentals, located at 1005 Riverside Drive in Palmetto, Florida, is a top tourist attraction offering boat rentals in the stunning waters of Palmetto, Bradenton, Anna Maria Island, and Tampa Bay. Whether you're looking for a relaxing day on the water, thrilling fishing expeditions, or simply want to soak up the sun with your loved ones, Pirate Monkey Boat Rentals has the perfect vessel for you. Our membership discount program offers deeper discounts for high frequency renters, making us a great alternative to boat clubs. Located at Regatta Pointe Marina in Palmetto, FL, we serve the boating community of Palmetto, Bradenton, Anna Maria Island, and Lower Tampa Bay.

Suncoast Cleaning Errand Services, LLC is a family owned and operated business located at 1505 North Knollwood Drive in Bradenton, Florida. We specialize in Residential, Vacation, Commercial Cleaning, Property Management, and Errand Services. Our goal is to make life more enjoyable for our clients by taking care of tasks they don't have time for or simply don't want to do. We serve Sarasota, Bradenton, Lakewood Ranch, Longboat Key, and Anna Maria Island. Our team is licensed, insured, and all employees undergo level 2 background checks for your peace of mind. Let us handle the cleaning and errands so you can focus on what truly matters.

Blissful Bay at Bayside Bungalow is a charming lodging option located at 201 South Bay Boulevard in Holmes Beach, Florida. This three-bedroom, two-bathroom condo is beautifully decorated with a beachy theme, perfect for a relaxing getaway. Situated just across the street from the Bay beach, guests can enjoy easy access to the water as well as nearby restaurants and boutiques. The open living space features comfortable seating and a rustic dining room table, while the kitchen is fully equipped with essential dishware and appliances. The primary bedroom offers a cozy king-sized bed and ensuite bathroom, while both guest rooms boast picturesque water views. The property also includes a resort-style heated swimming pool, BBQ area, and laundry room. With its convenient location and comfortable amenities, Blissful Bay at Bayside Bungalow is the perfect choice for a memorable stay on Anna Maria Island.

Villa #2 Shrimp is a vibrant and beautifully decorated studio located at 3605 Gulf Drive in Holmes Beach, Florida. This lodging option is just a 2-minute walk to the beach and is dog-friendly. Guests can enjoy a shared pool, BBQ grill, and close proximity to restaurants and grocery stores. The bungalow has a kitchenette with stainless steel appliances, a cozy bistro table for two, and a comfortable outdoor seating area surrounded by tropical landscaping. The main bathroom features a sparkling walk-in shower and the unit includes a king bed. The property is part of the Islands West Resort, which offers several other villas for rent. Guests can easily explore Anna Maria Island with a trolley stop nearby. Managed by AMI Locals, this property is perfect for a relaxing vacation in a residential area. Previous guests have praised the location, pool, and overall experience, making it a highly recommended choice for a getaway.

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.

The Penthouses at Gulf Stream offer luxurious and spacious accommodations in the heart of Anna Maria, Florida. Located at 1501 Gulf Drive, this upscale lodging option provides stunning views of the Gulf of Mexico and easy access to the pristine beaches of the area. Each penthouse is elegantly furnished and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the convenience of nearby dining and shopping options, as well as outdoor activities such as fishing, kayaking, and beachcombing. Whether you're looking for a relaxing getaway or an adventurous vacation, the Penthouses at Gulf Stream are the perfect choice for your stay in Anna Maria.

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.

Casa Sierra Rental is a reputable real estate agency located at 205 36th Street in Holmes Beach, Florida, United States. We specialize in providing top-notch rental properties for vacationers looking to experience the beauty of Anna Maria Island. Our team is dedicated to helping clients find the perfect rental home that fits their needs and budget. Whether you are looking for a cozy beach cottage or a luxurious waterfront villa, Casa Sierra Rental has a wide selection of properties to choose from. Contact us today to start planning your dream vacation on Anna Maria Island!

Wish Upon A Starfish is a real estate and travel agency located at 411 80th Street in Holmes Beach, Florida, United States. This Key West style 3 bedroom home offers a peaceful and relaxing retreat on Anna Maria Island. With vaulted ceilings, an open floor plan, and a private heated pool, this paradise found is perfect for families looking for a beach getaway. The fully equipped kitchen, spacious front deck, and cozy living room provide all the comforts of home. The home is family-friendly, with amenities such as a pack n' play, high chair, and baby gates provided. Children will love the bunk bed room with its own private bathroom, while adults can relax in the Queen size guest bedroom with an adjustable bed.

Coldwell Banker Realty is a premier real estate agency located at 100 North Tamiami Trail in Sarasota, Florida. Our office is conveniently situated near the Ritz and Westin, making it easily accessible for all of Sarasota. With over 150 agents, we have a strong customer service reputation and make a significant impact on the real estate market in Sarasota and Manatee Counties. Our office serves a wide range of areas including Sarasota, Bradenton, Bradenton Beach, Lakewood Ranch, Longboat Key, Siesta Key, Venice, Nokomis, Osprey, Anna Maria, and Holmes Beach. We offer a variety of properties including luxury homes, condominiums, new construction, resales, commercial properties, condo-hotels, and fractional ownership. Our experienced agents have received national recognition for their dedication and production.

AMI Adventures Boat Tours is a travel agency located at 5325 Marina Drive in Holmes Beach, Florida, United States. We offer a variety of exciting activities such as Dolphin tours, Sunset Cruises, Fishing Charters, Parasailing, Banana boat rides, Jet ski Rentals and tours, and more. Owned and Operated by true Anna Maria Island Natives, we are dedicated to providing you with the best experiences our home has to offer. In addition to our regular tours and activities, we now offer Comedy Tours every Friday night for a unique and entertaining experience. Whether you're looking for a relaxing sunset cruise or a fast-paced banana boat ride, we have something for everyone in the family to enjoy. Book your adventure with AMI Adventures Boat Tours for a vacation that you'll never forget!

AMI Escapes Boat Tours is located at 6398 Marina Way in Holmes Beach, Florida. It is Anna Maria Island's most popular adventure boat tour, offering private and all-inclusive experiences customized for each group. Guests have the opportunity to visit secluded islands, beaches, and sandbars such as Egmont Key, Passage Key, Jewfish Key, and Beer Can Island. The tours include amenities such as paddle boards, snorkeling gear, fishing poles, and underwater scooters, with no set schedule so guests can enjoy the experience for as long as they desire. In addition to island hopping, the tours also offer stops at local restaurants and opportunities for swimming, snorkeling, and paddle boarding. The institution also offers dolphin tours, snorkeling trips with underwater scooters, and sunset cruises with a premium Bluetooth sound system. With comfortable boats, complimentary water and soft drinks, and the option to bring adult beverages on board, AMI Escapes Boat Tours provides a luxurious and customizable boating experience for visitors to Anna Maria Island, Longboat Key, and Bradenton Beach.