Charming rental cottages in Anna Maria, Florida

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.

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.

Sunrise Garden Resort on Anna Maria Island by Vacasa is a charming lodging option located at 512 Spring Avenue in Anna Maria, Florida, United States. Whether you are planning a romantic getaway, a family vacation, or a solo retreat, this resort offers a variety of vacation rentals to suit your needs. Guests can enjoy the convenience of internet access in 16 of the vacation rentals, allowing them to stay connected during their stay. Additionally, pet owners can bring their furry friends along, as 16 of the homes at Sunrise Garden Resort are dog-friendly (be sure to check individual listings for any restrictions).

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.

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.

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.

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.

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.

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.

Lazy Palm Cottage is a little piece of paradise located in Holmes Beach on Anna Maria Island, Florida. This classic 1930's beach cottage has been beautifully renovated to offer all the modern comforts needed for a fabulous vacation. With 3 bedrooms and 2 baths, the split floor plan comfortably sleeps 6 guests. The cottage is bright and spacious, with over 1500 sq ft of indoor living space and an additional 380 sq ft of covered outdoor porches. Guests can enjoy the large open living area, lower family room leading to the private pool, and another sitting room off the kitchen. The fully equipped kitchen features dual sinks, an extra refrigerator for drinks, and an ice maker. Outside, guests can relax by the heated private pool, on the poolside patio with chaise lounges, or under the covered patio with ceiling fans. An outdoor shower and propane gas grill are also available for guests to use.

Blue Turtle Cottage is a charming vacation rental located on Anna Maria Island in Holmes Beach, Florida. Just a minute walk to the beautiful white sandy beaches, this cottage offers a perfect tropical escape. The fully equipped kitchen, cozy living room, and private bedrooms ensure a comfortable stay for guests. The private backyard features a sparkling pool, outdoor dining area, and BBQ grill for relaxing evenings. With easy access to the beach and nearby amenities, guests can enjoy the laid-back atmosphere of Anna Maria Island. The property also offers personalized service and assistance to make your stay memorable. Whether you're looking for adventure or relaxation, Blue Turtle Cottage is the perfect destination year-round. Explore the island, dine at local restaurants, or simply unwind by the pool - the choice is yours. Book your stay at Blue Turtle Cottage for a truly unforgettable vacation experience on Anna Maria Island.

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.

Anna Maria Island is a charming institution located at 5315 Gulf Drive in Holmes Beach, Florida, United States. This unique establishment offers a variety of services including food, real estate agency, restaurant, and travel agency. Whether you are looking to enjoy a delicious meal, find your dream home, or plan a vacation getaway, Anna Maria Island has something for everyone. With its picturesque location and exceptional offerings, it is the perfect destination for those seeking a memorable experience on the beautiful Gulf Coast.

Welcome to Anna Maria Life Real Estate, your premier resource for all things Anna Maria Island. Located at 9908 Gulf Drive, Anna Maria, Florida, we specialize in connecting clients with the finest properties on this enchanting island. Whether you're buying your first home, looking for an investment property, or selling, we are here to ensure a seamless and fulfilling real estate journey. Anna Maria Island is a unique blend of breathtaking beauty and coastal charm, featuring pristine beaches, vibrant sunsets, and a relaxing pace of life. Our comprehensive listings include charming coastal cottages, modern estates, and beachfront properties, each reflecting the island's enchanting essence. We understand that buying a property here is more than just a transaction; it's about embracing a lifestyle.

Welcome to Green Real Estate-Anna Maria, your trusted partner in finding the perfect home and unforgettable travel experiences on the beautiful Anna Maria Island. Conveniently located at 9906 Gulf Drive, Anna Maria, Florida, our unique blend of real estate and travel services offers a comprehensive approach to island living and exploration. As a premier real estate agency, we specialize in helping you discover your dream property, whether it's a charming beachfront cottage, a luxurious coastal estate, or a cozy vacation rental. Our team of experienced and dedicated real estate professionals is committed to providing personalized service, ensuring that you find the perfect home that fits your lifestyle and needs.

Welcome to Galletto Team at Island Real Estate of Anna Maria Island! Conveniently located at 6101 Marina Drive in the charming Holmes Beach, Florida, our dedicated team of real estate professionals is committed to helping you find your dream home or investment property on the beautiful Anna Maria Island. With years of local expertise and a passion for exceptional customer service, we specialize in a wide range of real estate services, including buying, selling, and property management. Our intimate knowledge of the island and its unique neighborhoods allows us to offer personalized guidance tailored to your specific needs and preferences. Whether you're looking for a cozy beach cottage, a luxurious waterfront estate, or a lucrative rental property, the Galletto Team is here to make your real estate journey smooth and successful.

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.

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.

Bay Breezes at Bayside Bungalow is a charming lodging option located at 201 South Bay Boulevard in Holmes Beach, Florida. This vacation retreat offers two bedrooms and one bathroom, tastefully decorated in a coastal theme for a perfect beach getaway. Guests can enjoy a private patio with stunning water views across the bay, as well as a shared pool, BBQ area, and easy access to both Gulf and Bay beaches. The interior features a relaxing seating area with a large TV, a well-equipped kitchen, and comfortable bedrooms with premium mattresses. The resort-style heated swimming pool and outdoor living spaces provide ample opportunities for relaxation and enjoyment. With a maximum of one car allowed for parking and pet-friendly accommodations, Bay Breezes at Bayside Bungalow is the ideal choice for a memorable vacation experience in Bradenton Beach, Florida.

Bayside Cutie at Bayside Bungalow is a charming lodging option located at 201 South Bay Boulevard in Holmes Beach, Florida. This one-bedroom, one-bathroom getaway offers a private patio area for enjoying the Florida sunshine. Guests can take advantage of the shared pool, BBQ area, and proximity to both the Bay beach and Gulf beach. The interior of the living space exudes a warm, beachy atmosphere, with a comfortable sofa, TV, and fully equipped kitchen. The primary bedroom features chic furnishings and an ensuite bathroom with a walk-in shower. Additional sleeping space is available on the sleeper sofa in the living room. Bayside Bungalow is part of a unique bayside duplex with resort-style amenities, including a heated swimming pool, laundry room, and outdoor living area with BBQ grills and a cabana. Guests can also explore the nearby restaurants and boutiques. Whether you're looking for a relaxing retreat or a fun-filled beach vacation, Bayside Cutie at Bayside Bungalow has something for everyone.

Villa #4 Sand Dollar is a charming lodging located at 3605 Gulf Drive in Holmes Beach, Florida, United States. This cozy villa offers a relaxing retreat just steps away from the beautiful beaches of Anna Maria Island. The villa is tastefully decorated and fully equipped with modern amenities to ensure a comfortable stay for guests. With its convenient location, guests can easily explore the island's attractions, shops, and restaurants. Whether you're looking for a romantic getaway or a family vacation, Villa #4 Sand Dollar provides the perfect accommodation for your stay in sunny Florida.

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.

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.

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.

Shady Mango is a unique institution located at 417 Pine Avenue in the charming town of Anna Maria, Florida, United States. As a dual-purpose establishment, Shady Mango serves as both a real estate agency and a travel agency, offering a one-stop shop for all your property and vacation needs. Whether you're looking to buy or sell a home in the sunny paradise of Anna Maria Island, or seeking assistance in planning your dream getaway to this beautiful destination, Shady Mango is here to help. With a team of experienced professionals and a commitment to exceptional customer service, Shady Mango is your go-to destination for all things real estate and travel in Anna Maria.

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.