TOP 30 Best Luxury property in Holmes Beach, Florida

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.

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!

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.

Coldwell Banker Realty is a premier real estate agency located at 100 North Tamiami Trail in Sarasota, Florida. Our office is conveniently situated near the Ritz and Westin, making it easily accessible for all of Sarasota. With over 150 agents, we have a strong customer service reputation and make a significant impact on the real estate market in Sarasota and Manatee Counties. Our office serves a wide range of areas including Sarasota, Bradenton, Bradenton Beach, Lakewood Ranch, Longboat Key, Siesta Key, Venice, Nokomis, Osprey, Anna Maria, and Holmes Beach. We offer a variety of properties including luxury homes, condominiums, new construction, resales, commercial properties, condo-hotels, and fractional ownership. Our experienced agents have received national recognition for their dedication and production.

Welcome to Coldwell Banker Realty - Siesta Key, your premier real estate agency located in the heart of the vibrant and picturesque village of Siesta Key, Sarasota, Florida. Nestled at 5145 Ocean Boulevard, our office enjoys a prime location that captures the essence of this tropical paradise, renowned for its stunning beaches, exceptional dining, lively music, and eclectic shopping experiences. Our Siesta Key office is a hub of activity, attracting a diverse clientele from local residents to international visitors, all drawn by the allure of our prominently displayed property listings. With over 70 dedicated and experienced independent sales associates, we are committed to providing unparalleled customer service, ensuring you find the perfect property to match your lifestyle.

Tiffany Place Condo is a luxurious beachfront condominium located at 7000 Gulf Drive in Holmes Beach, Florida. This stunning property offers breathtaking views of the Gulf of Mexico and is just steps away from the pristine white sandy beaches. The condo features beautifully appointed units with modern amenities, spacious layouts, and private balconies overlooking the ocean. Residents can enjoy access to a swimming pool, tennis courts, and a fitness center, as well as convenient proximity to shopping, dining, and entertainment options. Experience the ultimate beachfront living at Tiffany Place Condo.

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.

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.

Villa #2 Shrimp is a vibrant and beautifully decorated studio located at 3605 Gulf Drive in Holmes Beach, Florida. This lodging option is just a 2-minute walk to the beach and is dog-friendly. Guests can enjoy a shared pool, BBQ grill, and close proximity to restaurants and grocery stores. The bungalow has a kitchenette with stainless steel appliances, a cozy bistro table for two, and a comfortable outdoor seating area surrounded by tropical landscaping. The main bathroom features a sparkling walk-in shower and the unit includes a king bed. The property is part of the Islands West Resort, which offers several other villas for rent. Guests can easily explore Anna Maria Island with a trolley stop nearby. Managed by AMI Locals, this property is perfect for a relaxing vacation in a residential area. Previous guests have praised the location, pool, and overall experience, making it a highly recommended choice for a getaway.

The Casitas Coral Reef is a real estate and travel agency located at 1123 Crescent Street in Sarasota, Florida, United States. Specializing in Florida Beach House Rentals in Sarasota and Holmes Beach, the agency offers luxurious accommodations for up to 12 guests at The Casitas at Siesta Key and a beautiful retreat for 6 at The Tree House at Anna Maria Island in Holmes Beach. With stunning views and easy access to the number 1 beach in the USA, guests can expect a relaxing vacation packed with all the amenities they need. Established in 2018, The Casitas Coral Reef takes pride in providing comfortable and well-maintained vacation rentals for guests to enjoy. During the pandemic, the agency follows strict state guidelines regarding COVID-19 to ensure a safe and sanitized environment for guests. Whether it's a weekend getaway or a week-long vacation, The Casitas Coral Reef is dedicated to making your dream vacation a reality.

Welcome to Coldwell Banker Realty, your premier real estate agency located at 595 Bay Isles Parkway, Longboat Key, Florida. Nestled in the heart of the Charthouse, our prestigious Coldwell Banker PREVIEWS Sales Center is dedicated to providing exceptional service in the global luxury market. With a strong reputation built on personal, quality service, we offer comprehensive resources and innovative marketing programs to meet all your real estate needs. Our full-service real estate office specializes in exceptional properties across Longboat Key, St. Armand's Circle, Lido Key, Bird Key, Siesta Key, Casey Key, and Sarasota. Whether you are buying or selling, you will benefit from our unparalleled national and local strength in advertising, marketing, referrals, and technology.

Cypress Winds Apartment Homes is a charming community located at 6904 Manatee Avenue West in Bradenton, Florida. Situated just minutes from Holmes Beach, this prime location offers easy access to beautiful beaches, shopping centers, and business districts. The renovated kitchens in our spacious 1, 2, and 3 bedroom apartments feature stainless steel appliances and wood-style flooring. Each apartment also includes a screened lanai and ceiling fans for your comfort. Our community is surrounded by acres of lush tropical landscaping, with amenities such as two cobblestone-lined swimming pools, picnic and barbecue areas, a sand volleyball court, playground, and off-leash dog park. Whether you're looking to relax by the pool or enjoy a game of volleyball, Cypress Winds has everything you need to feel at home.

Sandy Point Condominiums by A Paradise Vacation Rentals is a premier real estate and travel agency located at 3607 East Bay Drive in Holmes Beach, Florida. Offering luxurious and spacious condominiums for vacation rentals, Sandy Point Condominiums provides guests with a paradise-like experience on the beautiful shores of Florida. With top-notch amenities and a prime location, guests can enjoy a relaxing and unforgettable getaway at this exclusive property. Experience the ultimate vacation escape at Sandy Point Condominiums by A Paradise Vacation Rentals.

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.

Welcome to A Paradise Realty, your premier destination for real estate and travel services in the heart of Holmes Beach, Florida. Conveniently located at 5201 Gulf Drive, our agency is dedicated to making your dreams of living or vacationing in paradise a reality. Whether you are looking to buy, sell, or rent a property, our experienced team of real estate professionals is here to guide you every step of the way. In addition to our exceptional real estate services, we also offer comprehensive travel planning to ensure your stay in Holmes Beach is nothing short of extraordinary. From finding the perfect vacation rental to arranging unforgettable local experiences, A Paradise Realty is your one-stop shop for all your property and travel needs.

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.

Welcome to AMI Real Estate, your trusted partner in finding the perfect property in the beautiful Holmes Beach, Florida. Conveniently located at 5306 Holmes Boulevard, we specialize in offering personalized real estate services to meet your unique needs. Whether you're looking to buy, sell, or rent a property, our team of experienced agents is dedicated to providing exceptional service and expert guidance throughout your real estate journey. Our deep knowledge of the local market ensures that we can help you find the ideal home or investment property on Anna Maria Island and the surrounding areas. At AMI Real Estate, we pride ourselves on our commitment to integrity, professionalism, and customer satisfaction. Contact us today to explore the vibrant lifestyle and stunning properties that Holmes Beach has to offer. Let us help you make your real estate dreams a reality.

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.

Villa Paradise is a luxurious beachfront institution located at 5608 Holmes Boulevard in Holmes Beach, Florida, United States. This stunning property offers guests a paradise-like experience with its spacious and beautifully decorated accommodations, breathtaking views of the Gulf of Mexico, and top-notch amenities. Whether you're looking to relax by the pool, soak up the sun on the white sandy beaches, or explore the nearby shops and restaurants, Villa Paradise has everything you need for a perfect vacation getaway. Come and experience the ultimate in luxury and comfort at Villa Paradise.

Laplage 9 is a luxurious beachfront vacation rental located at 6426 Gulf Drive in Holmes Beach, Florida. This stunning property offers guests a serene and stylish retreat with breathtaking views of the Gulf of Mexico. With spacious accommodations, modern amenities, and a prime location just steps from the sandy shores, Laplage 9 is the perfect destination for a relaxing getaway on Anna Maria Island. Whether you're looking to soak up the sun, explore the local attractions, or simply unwind in paradise, Laplage 9 has everything you need for a memorable vacation experience.

Azure Bliss Vacation Rental is a top-notch real estate and travel agency located at 304 60th Street in the beautiful Holmes Beach, Florida. Our agency specializes in providing luxurious vacation rentals for those looking to escape to paradise. With a wide selection of properties ranging from beachfront villas to cozy condos, we offer the perfect accommodations for every traveler's needs. Our dedicated team is committed to ensuring that each guest has a memorable and stress-free stay, making us a trusted choice for vacation planning in the area. Whether you're seeking a romantic getaway or a family-friendly retreat, Azure Bliss Vacation Rental has the perfect property waiting for you. Book your dream vacation with us today and experience the ultimate relaxation and comfort in sunny Florida!

Welcome to Becky Sirigotis, Realtor – Your Trusted Waterfront Expert and Curated Lifestyles Concierge, located at 6000 Marina Drive, Holmes Beach, Florida. Specializing in the vibrant Sarasota area, including Anna Maria Island and its sister islands, we offer a comprehensive, client-focused approach to real estate. Our services leverage local market insight, advanced negotiation expertise, and customized strategies to meet the unique needs and goals of both buyers and sellers. Sarasota and its surrounding islands blend vibrant arts and serene beach living, making it an ideal destination for those seeking a dynamic yet peaceful Gulf Coast lifestyle. From the cultural richness of Sarasota, home to the renowned Ringling Museum and a lively arts scene, to the tranquil beaches and charming local eateries on Anna Maria Island and Longboat Key, this area offers a perfect mix of cultural and coastal tranquility.

Welcome to Mel & Barbara Neely Real Estate, your trusted partner in finding the perfect home or investment property in the beautiful Holmes Beach, Florida. Located at 3001 Gulf Drive, our agency is dedicated to providing personalized and professional real estate services to both buyers and sellers in the vibrant community of Holmes Beach and the surrounding areas. With years of experience and a deep understanding of the local market, Mel & Barbara Neely Real Estate is committed to helping you navigate the complexities of real estate transactions with ease and confidence. Whether you're looking for a charming beachfront cottage, a spacious family home, or a lucrative investment opportunity, our team is here to guide you every step of the way.

Welcome to Premier Real Estate, your trusted partner for all your real estate needs in the beautiful coastal community of Holmes Beach, Florida. Situated in the heart of Anna Maria Island, our agency specializes in providing exceptional service and expertise to help you find your dream home or investment property in this picturesque paradise. At Premier Real Estate, we understand that buying or selling property is more than just a transaction; it's a life-changing experience. That's why our team of dedicated and experienced real estate professionals is committed to delivering personalized service tailored to your unique needs and preferences. Whether you're looking for a charming beachfront cottage, a luxurious waterfront estate, or a cozy condo with stunning views, we have the local knowledge and industry expertise to guide you every step of the way.

Welcome to Molly Taylor, Realtor - Mike Norman Realty, your trusted partner in finding the perfect home in the beautiful coastal community of Holmes Beach, Florida. Conveniently located at 3101 Gulf Drive, we specialize in helping you navigate the vibrant real estate market of Anna Maria Island and its surrounding areas. Whether you're looking for a charming beachfront cottage, a luxurious waterfront estate, or a cozy family home, Molly Taylor offers personalized service and expert guidance to make your real estate journey seamless and enjoyable. With an in-depth knowledge of local market trends and a commitment to client satisfaction, Molly is dedicated to turning your property dreams into reality. Contact us today and discover why so many clients choose Molly Taylor, Realtor - Mike Norman Realty, for their real estate needs on Florida's stunning Gulf Coast.