TOP 30 Rental spaces 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.

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).

ABC Baby and Beach Equipment Rentals is a premier rental service located at 2239 15th Street in Sarasota, Florida. We specialize in providing high-quality baby supplies and beach gear for rent in Sarasota, Siesta Key, Lakewood Ranch, Anna Maria Island, and Bradenton. Our delivery and pick-up process is convenient and hassle-free, with deliveries made before standard check-in times and returns scheduled after check-out. We offer free delivery on orders over $150 to most zip codes, with no additional service charges.

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.

Welcome to Island Tides Vacation Rental, your premier destination for unforgettable getaways on the stunning Gulf Coast. Located at 1110 Via De Luna Drive, Pensacola Beach, Florida, our business combines the expertise of a real estate and travel agency to offer you the finest selection of vacation properties. Whether you're seeking a serene escape or a family adventure, we have the perfect accommodations to suit your needs. Explore our diverse portfolio of 33 meticulously curated properties, each offering unique experiences and luxurious amenities. From the pet-friendly charm of Aloha by the Sea, with its breathtaking views and wrap-around porch, to the opulence of Aqua Palms, featuring a private heated pool and spacious lawn, your ideal vacation home awaits.

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.

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.

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.

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.

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.

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.

Kokomo Charters is a luxury travel agency located at 5 Bayfront Drive in Sarasota, Florida. We specialize in providing private boat charters in the Sarasota area, including Siesta Key, Anna Maria Island, Lido Key, Casey Key, and Longboat Key. Our visitors consistently praise us as the highlight of their vacation, while locals book us regularly to impress their guests. Our fleet includes the beautiful 37-foot Sea Ray "Top Shelf" and the massive 50-foot three-story yacht "Memory Maker." Both vessels are yacht certified and offer a luxurious and upscale boating experience unlike any other in the market. Each charter is completely customized to your preferences, ensuring an unforgettable day for you and your crew.

Welcome to Between The Tides, your premier destination for real estate and travel experiences in the heart of Florida's Gulf Coast. Nestled at 3721 116th Street West, Bradenton, Florida, our unique agency offers a blend of accommodation and adventure, perfect for those looking to explore the stunning beauty of Anna Maria Island, Bradenton, and the historic charm of Cortez. Discover the allure of coastal living with our charming 1 Bed/1 Bath property, thoughtfully designed to provide both comfort and convenience. With a Queen bed, Sofa Sleeper, child-size bunks, and a futon in the Lanai, this cozy retreat accommodates up to six guests. Enjoy the open layout with a work/desk area, a fully equipped kitchen, and a spacious Lanai that extends to a breezy back patio, creating a perfect space for relaxation.

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: