TOP 30 Relaxing beach vacation homes for rent 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!

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.

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.

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.

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.

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.

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.

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.

Bay Vista at Bayside Bungalow is a luxurious lodging option located at 201 South Bay Boulevard in Holmes Beach, Florida. This second-floor condo offers stunning views of the bay from its 180-degree wrap-around windows, allowing guests to watch sailboats, dolphins, and beautiful sunrises. The unit features three bedrooms, two bathrooms, and a fully equipped kitchen with stainless steel appliances. Guests can relax in the cozy living area or enjoy meals at the rustic dining table. The property also offers shared amenities such as a resort-style heated swimming pool, BBQ area, and cabana. With its convenient location near Gulf and Bay beaches, restaurants, and boutiques, Bay Vista at Bayside Bungalow is the perfect vacation destination for a relaxing and enjoyable stay in Bradenton Beach, Florida.

Nautilus Condominiums is a luxurious real estate and travel agency located at 7100 Gulf Drive in Holmes Beach, Florida, United States. Our stunning beachfront condos offer breathtaking views of the Gulf of Mexico and provide the perfect setting for a relaxing vacation or a permanent home. With top-notch amenities and a prime location, Nautilus Condominiums is the ideal choice for those looking to experience the beauty and tranquility of Anna Maria Island. Contact us today to learn more about our available properties and start planning your next getaway in paradise.

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.

OHasis Getaway is a real estate and travel agency located at 211 Elm Avenue in Anna Maria, Florida, United States. Just steps away from the stunning Gulf side beaches of Anna Maria Island, our locations are perfect for a relaxing escape. We take pride in providing Midwestern care to ensure your OHasis Getaway is prepared for you to simply enjoy island life. Our properties offer luxurious comfort in soothing island style, allowing you to unwind and recharge. With beautiful sunrises and sunsets, lush flora, and soft sugar sand beaches, you'll feel like you're in paradise. Enjoy amenities such as private pools, outdoor grills, entertainment systems, and fully stocked kitchens with Starbucks coffee beans provided.

Welcome to Villa #1 Sailfish by AMI Locals, your perfect getaway on beautiful Anna Maria Island. Nestled at 3605 Gulf Drive, Holmes Beach, Florida, this charming two-bedroom, two-bath villa is a mere two-minute stroll from the pristine Gulf of Mexico beaches. Part of the picturesque Island West Resort, Villa #1 Sailfish offers a delightful blend of comfort and convenience, ideal for families, couples, and friends traveling together. Highlights of Villa #1 Sailfish include: