TOP 10 Vacation cottage rentals near me in Anna Maria, Florida

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!

Sato Real Estate & Vacation Rentals is a premier real estate agency and travel agency located at 519 Pine Avenue in Anna Maria, Florida. Specializing in vacation rentals, they offer a wide range of properties to choose from for your next getaway. With a team of experienced agents, Sato Real Estate & Vacation Rentals is dedicated to providing top-notch customer service and helping clients find their dream vacation rental or investment property in the beautiful surroundings of Anna Maria. Whether you are looking for a beachfront villa, a cozy cottage, or a luxury condo, Sato Real Estate & Vacation Rentals has something for everyone. Plan your next vacation or investment with Sato Real Estate & Vacation Rentals and experience the best of Anna Maria, Florida.

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.

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.

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.

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.

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.

Duncan Real Estate & Vacation Rentals is a premier real estate and travel agency located at 310 Pine Avenue in Anna Maria, Florida. With a wide range of properties available for both long-term and vacation rentals, as well as homes for sale, Duncan Real Estate & Vacation Rentals is dedicated to helping clients find the perfect property to suit their needs. Whether you are looking for a beachfront vacation rental or a permanent residence in the beautiful Anna Maria area, our experienced team of agents is here to assist you every step of the way. Contact us today to start your search for your dream home or vacation getaway.

Serendipity Anna Maria is a real estate and travel agency located at 101 South Bay Boulevard in Anna Maria, Florida, United States. Our dedicated team follows our core values of “C.A.R.E.” to ensure that your vacation experience is unforgettable. From exploring the local museums, churches, and markets with a guide to planning the perfect golf getaway, we are here to make sure your stay on Anna Maria Island is relaxing and fun. Our luxurious vacation homes in Anna Maria Island and Park City are designed to provide a cozy and comfortable experience. Whether you choose to stay in one of our properties in Florida or Utah, we guarantee that you will have a trip to remember. Let Serendipity Anna Maria take care of the details so you can focus on enjoying your vacation to the fullest.

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.

Anna Maria Island Accommodations is a premier real estate and travel agency located at 3018 Avenue C in Holmes Beach, Florida. Specializing in vacation rentals and property management, our team is dedicated to providing top-notch accommodations and exceptional service to our clients. Whether you are looking for a beachfront villa, a cozy cottage, or a luxury condo, we have a wide range of options to suit your needs. Our knowledgeable staff is here to help you find the perfect vacation rental for your stay on beautiful Anna Maria Island. Contact us today to start planning your dream getaway!

Portfolio Vacations is a boutique property management and travel agency located at 2501 Gulf Drive North in Bradenton Beach, Florida. As a locally owned and operated company on Anna Maria Island, we pride ourselves on providing our guests with a 5-star experience every day. Our small size allows us to pay attention to every detail, ensuring that we know each property inside and out. With a plethora of vacation rentals on the island, we understand that you have options, but we believe that you will see the difference when booking with us. Choose Portfolio Vacations for your next vacation and let us help you create lasting memories on Anna Maria Island.

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 Vacations is a premier real estate and travel agency located in Holmes Beach, Florida. Situated at 3018 Avenue C, this institution specializes in providing top-notch vacation rental properties on Anna Maria Island. Whether you are looking for a beachfront condo, a cozy cottage, or a luxurious villa, Anna Maria Vacations has a wide selection of accommodations to suit every traveler's needs. With exceptional customer service and a commitment to creating unforgettable vacation experiences, Anna Maria Vacations is the perfect choice for your next getaway to this beautiful destination.

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.

Cindy Quinn PA is a renowned real estate professional at Sato Real Estate, located on Anna Maria Island in Florida. With over 25 years of experience, Cindy is consistently ranked in the top 1% of Florida Realtors and holds prestigious designations such as the Million Dollar GUILD and Certified Luxury Home Marketing Specialist. Her strong work ethic, integrity, and passion for helping clients achieve their real estate goals have earned her a stellar reputation in the industry. Specializing in the Anna Maria Island and Bradenton communities, Cindy is well-connected and has a deep understanding of the local market trends, schools, and political issues that impact real estate. She is committed to providing superior client service with attention to detail, urgency, and a reputation for quality and kindness that clients can rely on.

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.

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.

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.