TOP 30 Beach vacation home rentals in Anna Maria, Florida

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Anna Maria Island Getaway is a premier real estate and travel agency located in Bradenton Beach, Florida. Our dedicated team is committed to helping you find the perfect getaway on the beautiful Anna Maria Island. Whether you're looking for a beachfront vacation rental, a cozy cottage, or a luxurious villa, we have a wide selection of properties to choose from. Our experienced staff is here to assist you every step of the way, from booking your accommodation to planning your itinerary. Come experience the beauty and tranquility of Anna Maria Island with us at Anna Maria Island Getaway.

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!

Reunion Vacation Homes is a lodging, real estate, and travel agency located at 7531 Osceola Polk Line Road in Davenport, Florida, United States. Specializing in bringing friends and family together in Orlando Vacation Home Rentals and Anna Maria Island Rentals, Reunion Vacation Homes offers a wide range of vacation rentals in select Orlando area resorts close to Disney® such as Reunion Resort, The Retreat at Champions Gate, Windsor at Westside, and more. With options ranging from 2-3 bedroom condos to 10-14 bedroom luxury villas, there is something for everyone. Whether you're looking for top villa rentals near Disney World® in Kissimmee & Davenport, or luxury mansions in Reunion Resort, Reunion Vacation Homes has you covered. With over 300 luxury villas and condos to choose from, guests can enjoy amenities such as private pools, golf course views, and proximity to major attractions.

Anna Maria Island Vacation Rentals is a premier real estate and travel agency located at 601 Gulf Drive North in Bradenton Beach, Florida. Specializing in luxury vacation rentals on the stunning Anna Maria Island, this agency offers a wide range of accommodations to suit every traveler's needs. From beachfront condos to cozy cottages, guests can expect top-notch service and amenities during their stay. Whether you're looking for a romantic getaway or a family-friendly retreat, Anna Maria Island Vacation Rentals has the perfect property for your next vacation. Experience the beauty and charm of Florida's Gulf Coast with a stay at one of their exceptional rental properties.

Island Real Estate Vacations on Anna Maria Island is a premier real estate and travel agency located at 3909 East Bay Drive in Holmes Beach, Florida. With a wide range of vacation rental properties available, they provide visitors with the perfect accommodations to enjoy all that this beautiful island has to offer. Whether you're looking for a beachfront villa, a cozy cottage, or a luxurious condo, Island Real Estate Vacations has something for everyone. Their knowledgeable staff is dedicated to ensuring a seamless and memorable vacation experience for all guests. Experience the beauty and tranquility of Anna Maria Island with Island Real Estate Vacations.

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.

Silver Surf Anna Maria Island is a charming lodging located at 1301 Gulf Drive North in Bradenton Beach, Florida. This cozy retreat offers a peaceful and relaxing atmosphere with stunning views of the Gulf of Mexico. The institution features comfortable and well-appointed rooms, perfect for a beach getaway or a romantic escape. Guests can enjoy amenities such as a swimming pool, free Wi-Fi, and easy access to the beach. Whether you're looking for a weekend retreat or an extended stay, Silver Surf Anna Maria Island provides a perfect home away from home on beautiful Anna Maria Island.

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.

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.

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.

AMI Beach Hut is a charming convenience store located at 9901 Gulf Drive in Anna Maria, Florida. This one-stop shop offers a variety of food items, snacks, drinks, and even liquor for your beach day essentials. Whether you need to grab a quick bite to eat or stock up on supplies for a day at the beach, AMI Beach Hut has you covered. Stop by and experience the convenience and friendly service that makes this store a favorite among locals and tourists alike.

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.

Anna Maria Island is a beautiful park located at 809 North Shore Drive in Anna Maria, Florida, United States. This serene and picturesque institution offers visitors a peaceful escape surrounded by stunning natural beauty. With its lush greenery, white sandy beaches, and crystal-clear waters, Anna Maria Island is the perfect spot for a relaxing day out in nature. Whether you're looking to sunbathe, swim, or simply take a leisurely stroll along the shore, this park has something for everyone to enjoy. Come and experience the tranquility and charm of Anna Maria Island for yourself.

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.

Osprey House Anna Maria is a premier real estate and travel agency located at 751 North Shore Drive in Anna Maria, Florida, United States. Our experienced team specializes in helping clients find their dream vacation rental or purchase their ideal beachfront property on the stunning Anna Maria Island. With a focus on personalized service and attention to detail, we strive to make the process of buying, selling, or renting a home as seamless and enjoyable as possible. Whether you are looking for a relaxing getaway or a permanent slice of paradise, Osprey House Anna Maria is here to help you every step of the way. Contact us today to start your journey towards owning a piece of this beautiful 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.

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!

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.

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.

Horizon Realty of Anna Maria is a reputable real estate agency located at 420 Pine Avenue in the charming coastal town of Anna Maria, Florida. Specializing in buying, selling, and renting properties in this beautiful area, our experienced team of agents is dedicated to providing top-notch service and expertise to our clients. Whether you are looking for a vacation rental, a new home, or an investment property, Horizon Realty of Anna Maria is here to help you navigate the real estate market with confidence and ease. Contact us today to start your real estate journey in this stunning beachside community.

SeaBreeze Vacation LLC is a full-service real estate and travel agency located at 5372 Gulf Drive in Holmes Beach, Florida, United States. Our Reservation Specialists are available 9 AM-Midnight EST, 7 days a week to help you find the perfect vacation home on Anna Maria Island. We offer a variety of homes for couples, families, and large groups, with amenities such as pet-friendly options, properties with docks, and golf cart rentals for easy island exploration. When you book directly with SeaBreeze Vacation, you can enjoy the best rates with no hidden fees. Our flexible cancellation policy allows you to cancel bookings up to 14 days before check-in and receive a refund. Our staff, who are either island locals or longtime transplants, are always available to assist with any needs or maintenance during your stay.

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.

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.

Beach Basket is a charming real estate and travel agency located at 111 Oak Avenue in Anna Maria, Florida. Specializing in vacation rentals, we offer a variety of beautiful properties on Anna Maria Island and the surrounding area. Our guests rave about the convenience and comfort of our accommodations, with amenities such as fully stocked kitchens, beach gear, and even outdoor showers. Whether you're looking for a cozy beach cottage or a secluded hideaway, we have the perfect property for your next getaway. Our dedicated team works hard to ensure that your stay is stress-free and enjoyable, while also taking great care of our property owners' homes. Experience the beauty of Anna Maria Island with Beach Basket - your home away from home in paradise.

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.