TOP 30 Relaxing beach vacation in Anna Maria, Florida

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Once Upon A Beach Vacation Rentals is a charming real estate agency located at 411 Pine Avenue in the beautiful beach town of Anna Maria, Florida. Our agency specializes in providing top-notch vacation rental properties for visitors looking to experience the ultimate beach getaway. Whether you're seeking a cozy beachfront cottage or a luxurious seaside villa, our dedicated team is here to help you find the perfect accommodations for your dream vacation. With our convenient location and personalized service, Once Upon A Beach Vacation Rentals is your go-to destination for a memorable and relaxing beach vacation in sunny Florida.

Anchor Down Real Estate & Rentals on Anna Maria Island offers top Bradenton & Anna Maria Island vacation rentals. Located at 9801 Gulf Drive in Anna Maria, Florida, this institution serves as a lodging, real estate, and travel agency. With a "No Worry Guest Guarantee" from reservation to check-out, Anchor Down Vacation Rentals provides the finest homes on the Florida Gulf Coast. Guests can enjoy spacious accommodations, beautiful outdoor areas, and excellent customer service. Whether you're looking for a family gathering, a romantic getaway, or a relaxing vacation, Anchor Down Vacation Rentals has the perfect property for you. Book today and experience the beauty of Anna Maria Island with Anchor Down!

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.

Tropic Isle at Anna Maria Island Inn is a charming lodging establishment located at 101 22nd Street North in Bradenton Beach, Florida. Situated on the beautiful Anna Maria Island, this inn offers guests a peaceful and relaxing retreat with easy access to the beach and local attractions. The accommodations are comfortable and well-appointed, providing a cozy home away from home for travelers. With its tropical atmosphere and friendly staff, Tropic Isle at Anna Maria Island Inn is the perfect destination for a memorable vacation in sunny Florida.

Anna Maria Island Beach Resort is a charming lodging located at 105 39th Street in Holmes Beach, Florida. Situated on the beautiful Anna Maria Island, this resort offers guests a relaxing and luxurious beachfront experience. With stunning views of the Gulf of Mexico, guests can enjoy pristine white sandy beaches and crystal clear waters right at their doorstep. The resort features comfortable accommodations, a swimming pool, and easy access to a variety of dining and shopping options. Whether you're looking for a romantic getaway or a fun family vacation, Anna Maria Island Beach Resort is the perfect destination for a memorable stay in sunny 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.

Haley's at Anna Maria Island Inn is a charming lodging establishment located at 8102 Gulf Drive in Holmes Beach, Florida, United States. Situated on beautiful Anna Maria Island, this cozy inn offers comfortable accommodations and personalized service for a relaxing and enjoyable stay. Guests can enjoy easy access to the beach, as well as nearby shopping, dining, and recreational activities. With its tranquil atmosphere and convenient location, Haley's at Anna Maria Island Inn is the perfect choice for a memorable getaway on Florida's Gulf Coast.

The Blue Dolphin Inn by Island Vacation Properties is a charming lodging located at 780 Jacaranda Road in Anna Maria, Florida, United States. This cozy inn offers comfortable accommodations and a peaceful atmosphere for guests looking to relax and unwind. With its convenient location near the beach and local attractions, the Blue Dolphin Inn is the perfect destination for a beach getaway or a weekend retreat. Experience warm hospitality and personalized service at this lovely property during your stay in Anna Maria.

The Pelican Post at Anna Maria Island Inn is a charming lodging located at 202 1st Street North in Bradenton Beach, Florida. This cozy inn offers comfortable accommodations and a peaceful atmosphere for guests looking to unwind and relax. With its convenient location near the beach and various attractions, The Pelican Post is the perfect choice for a memorable stay on Anna Maria Island. Whether you're seeking a romantic getaway or a family vacation, this welcoming inn provides all the comforts and amenities you need for a pleasant stay in sunny Florida.

The Retreat at Anna Maria Island Inn is a charming lodging establishment located at 2305 Gulf Drive North in Bradenton Beach, Florida. Situated on the beautiful Anna Maria Island, this inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With cozy accommodations, stunning ocean views, and a convenient location near the beach, shops, and restaurants, The Retreat is the perfect destination for a weekend getaway or extended vacation. Whether you're looking to unwind by the pool, explore the island's natural beauty, or simply relax in your comfortable room, The Retreat at Anna Maria Island Inn has everything you need for a memorable stay.

Anna Maria Island Beach Sands is a charming lodging institution located at 601 Gulf Drive North in Bradenton Beach, Florida. Situated right on the beautiful shores of Anna Maria Island, this beachfront property offers guests stunning ocean views and easy access to the pristine sandy beaches. The accommodations are cozy and comfortable, perfect for a relaxing getaway by the sea. With its convenient location, guests can enjoy a variety of water activities, shopping, dining, and exploring the local attractions. Whether you're looking for a romantic escape or a fun family vacation, Anna Maria Island Beach Sands provides the perfect setting for a memorable stay in sunny Florida.

Beach Bums Recreational Rentals & Gift Shop is a charming store located at 427 Pine Avenue in Anna Maria, Florida. This one-stop shop offers a wide range of recreational rentals such as beach chairs, umbrellas, bikes, kayaks, and paddleboards for visitors looking to enjoy the beautiful beaches of Anna Maria Island. In addition to rentals, the gift shop features a variety of beach-themed souvenirs, local artwork, and unique gifts perfect for commemorating your vacation or finding the perfect present for a loved one. Whether you're looking to relax on the beach or bring home a piece of Anna Maria Island, Beach Bums Recreational Rentals & Gift Shop has something for everyone.

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.

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.

Welcome to Smuggler's Cove Beach Resort, a charming lodging destination located at 1501 Gulf Drive North in Bradenton Beach, Florida. Situated in the heart of the United States, our resort offers a tranquil and picturesque setting for guests to relax and unwind. With easy access to the beautiful Gulf of Mexico, guests can enjoy a variety of water activities such as swimming, snorkeling, and kayaking. Our cozy accommodations provide a comfortable and inviting atmosphere, perfect for a romantic getaway or a family vacation. Come experience the beauty of Bradenton Beach at Smuggler's Cove Beach Resort.

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.

Anna Maria Life Vacation Rentals is a real estate and travel agency located at 9908 Gulf Drive in Anna Maria, Florida, United States. Your beach house is waiting for you at Anna Maria Island Vacation Rentals! Escape the hustle and bustle of everyday life and unwind on this beautiful island that offers endless activities and stunning beaches. With the convenient free island trolley service, exploring all that Anna Maria Island has to offer is a breeze. Whether you want to relax on the beach or try thrilling water sports like parasailing, this island has something for everyone. Guests have praised Anna Maria Life Vacation Rentals for their professionalism and excellent customer service. They make vacation planning easy and stress-free, ensuring that your stay on Anna Maria Island is unforgettable. By booking directly with Anna Maria Life Vacation Rentals, you can avoid third-party booking fees and receive personalized recommendations for your trip. The knowledgeable team at Anna Maria Life Vacation Rentals is always available to answer any questions and help you make the most of your vacation experience.

Adams Beach Apartments is a charming seaside retreat located at 204 Spring Lane in Anna Maria, Florida, United States. Nestled just steps away from the pristine white sands and crystal-clear waters of the Gulf of Mexico, this idyllic property offers guests a tranquil and relaxing getaway. The apartments are beautifully furnished and equipped with all the amenities needed for a comfortable stay, including fully equipped kitchens, spacious living areas, and private balconies or patios with stunning ocean views. Guests can also enjoy the on-site swimming pool, barbecue area, and easy access to a variety of local shops, restaurants, and attractions. Whether you're looking for a romantic escape, a family vacation, or a solo adventure, Adams Beach Apartments provides the perfect home away from home for your next beach getaway.

Vacation Anna Maria is a premier real estate and travel agency located at 107 Pine Avenue in Anna Maria, Florida. Specializing in luxurious vacation rentals and property management services, Vacation Anna Maria offers guests a wide array of stunning beachfront properties to choose from. Whether you're looking for a cozy beach cottage or a spacious waterfront villa, our dedicated team is committed to helping you find the perfect vacation rental for your stay on Anna Maria Island. With exceptional customer service and local expertise, Vacation Anna Maria is your go-to destination for a memorable and relaxing getaway in the beautiful Sunshine State.

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.

Ocean Walk by Anna Maria Vacations is a premier real estate and travel agency located at 117 Willow Avenue in Anna Maria, Florida. This institution offers a wide range of vacation rental properties, from cozy beachfront cottages to luxurious waterfront villas. With unmatched customer service and attention to detail, Ocean Walk by Anna Maria Vacations ensures that every guest's stay is unforgettable. Whether you're looking for a relaxing beach getaway or an adventurous outdoor excursion, this agency has the perfect accommodation for you. Experience the beauty of Anna Maria Island with Ocean Walk by Anna Maria Vacations.

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.

Vacation Cottages Anna Maria Island offers charming and comfortable cottage rentals in the picturesque Holmes Beach, Florida. Located at 206 Haverkos Court, our real estate and travel agency specializes in providing guests with the perfect vacation getaway. Whether you're looking for a romantic retreat or a family-friendly escape, our cottages are the ideal choice. With easy access to the stunning Anna Maria Island beaches and a variety of local attractions, our rentals provide the perfect home base for your next vacation. Book your stay with us today and experience the beauty and relaxation of Holmes Beach!

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.

Buddy's Beach House is a charming vacation rental located on Anna Maria Island in Holmes Beach, Florida. This beachy chic property is just 2 blocks away from the ocean, making it the perfect getaway for those looking to relax and unwind by the water. The house sleeps 4 guests and features two bedrooms with queen size beds, luxurious linens, and comfortable mattresses. The property also includes 1.5 bathrooms and a fabulous outdoor shower for rinsing off after a day at the beach.

Vacasa Anna Maria is a real estate and travel agency located at 3004 Avenue C in Holmes Beach, Florida, United States. Specializing in vacation rentals on Anna Maria Island, they offer a variety of homes for every getaway. With 65 pet-friendly properties, you can bring your furry friend along for the trip. Additionally, 199 of their rentals have internet access, allowing you to stay connected during your stay. The professional housekeeping team ensures that each home is clean and stocked with amenities, so all you have to do is relax and enjoy your vacation. Whether you're looking for a beachfront bungalow or a cozy cottage, Vacasa Anna Maria has the perfect place for your stay on Anna Maria Island.

Located at 304 63rd Street in Holmes Beach, Florida, the Tarpon House on Anna Maria Island is not your average vacation rental. This institution, which combines elements of a real estate agency and a travel agency, offers a truly luxurious experience for guests. Boasting one of the largest private pools and hot tubs on the island, the Tarpon House is a backyard oasis like no other. The property is filled with entertainment options, including a ping pong table, foosball table, putting green, pool basketball hoop, and a Tiki Hut stocked with games and toys for all ages. Designed and furnished by Judy C. Whitlock, this vacation home features 4 bedroom en-suites, including 3 King beds and a bunk room for the kids. The kitchen is fully equipped with all the appliances you could need, and there are two separate dining areas, a large island/living area, and even a gaming room for added fun. With plenty of space for large families and groups, the Tarpon House is the perfect choice for a multigenerational vacation.