TOP 30 Relaxing beach vacation in Holmes Beach, Florida

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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.

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.

Alamanda Villa is a charming lodging institution located at 102 39th Street in the beautiful beach town of Holmes Beach, Florida, United States. This cozy villa offers a peaceful and relaxing atmosphere for guests looking to unwind and enjoy a beach getaway. With its convenient location near the ocean, guests can easily access the sandy shores and enjoy the warm Florida sun. The villa offers comfortable accommodations and modern amenities to ensure a pleasant stay for all visitors. Whether you're looking for a romantic retreat or a fun family vacation, Alamanda Villa is the perfect choice for your stay in Holmes Beach.

Heron Hideaway at Driftwood #1 is a charming lodging option located at 5108 Gulf Drive in Holmes Beach, Florida, United States. This cozy retreat offers a peaceful and serene atmosphere, perfect for a relaxing getaway. The accommodations are beautifully decorated and fully equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning views of the surrounding area, including the nearby beach and wildlife. Whether you're looking for a romantic escape or a family vacation, Heron Hideaway at Driftwood #1 is the perfect choice for your next trip to Florida.

Escape to an island paradise at Palm Tree Villas, located at 207 66th Street in Holmes Beach, Florida. Our charming lodging institution offers a relaxing getaway surrounded by lush palm trees and just steps away from the beautiful beaches of Anna Maria Island. Enjoy spacious villas equipped with modern amenities, a private pool, and a serene tropical garden. Whether you're looking for a romantic retreat or a family vacation, Palm Tree Villas is the perfect destination for your island getaway.

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.

Bluegreen Resort Sixty-Six is a charming lodging establishment located at 6600 Gulf Drive in Holmes Beach, Florida, United States. This resort offers guests a relaxing and luxurious retreat with stunning views of the Gulf of Mexico. The accommodations are spacious and beautifully decorated, providing a comfortable and inviting atmosphere for guests to unwind and recharge. The resort also features a range of amenities including a swimming pool, fitness center, and on-site dining options. Whether you're looking for a romantic getaway or a fun-filled family vacation, Bluegreen Resort Sixty-Six is the perfect destination for your next trip to Florida.

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.

Jessie's Island Store is a charming convenience store located at 5424 Marina Drive in Holmes Beach, Florida. This cozy store offers a variety of food items, snacks, and everyday essentials for locals and tourists alike. Whether you need a quick bite to eat, a refreshing beverage, or some last-minute supplies for your beach day, Jessie's Island Store has you covered. Stop by and experience the friendly service and laid-back atmosphere that makes this store a beloved destination for residents and visitors in the area.

Joie Inn is a charming lodging establishment located at 3501 Gulf Drive in Holmes Beach, Florida, United States. Offering a cozy and comfortable retreat for guests, Joie Inn provides a peaceful and relaxing atmosphere for those looking to unwind and enjoy a leisurely vacation. With thoughtfully appointed rooms and friendly service, guests can expect a delightful stay at this inviting inn. Perfectly situated near the beach and other local attractions, Joie Inn is the ideal destination for a memorable getaway in beautiful Florida.

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 #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.

Villa #3 Seahorse is a charming lodging establishment located at 3605 Gulf Drive in Holmes Beach, Florida, United States. This cozy villa offers a relaxing tropical atmosphere with stunning views of the Gulf of Mexico. Guests can enjoy a peaceful getaway with easy access to the beach, as well as nearby dining and shopping options. The villa features comfortable accommodations, a fully equipped kitchen, and a private outdoor patio for guests to unwind and soak up the sunshine. Whether you're looking for a romantic retreat or a family vacation, Villa #3 Seahorse is the perfect destination for a memorable stay on Anna Maria Island.

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.

Villa Florence is a charming institution located at 4104 6th Avenue in Holmes Beach, Florida, United States. This elegant villa offers a tranquil and luxurious retreat for guests looking to escape the hustle and bustle of everyday life. With its beautiful architecture, lush gardens, and stunning views of the surrounding area, Villa Florence provides a peaceful and relaxing atmosphere for visitors to enjoy. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Villa Florence has everything you need to make your stay unforgettable. Experience the beauty of Holmes Beach and indulge in the comfort and hospitality of Villa Florence.

Breakers 3 is a charming institution located at 103 45th Street in Holmes Beach, Florida. This beachfront property offers a serene and relaxing atmosphere for guests looking to unwind and enjoy the beautiful surroundings of the Gulf Coast. With spacious accommodations and top-notch amenities, Breakers 3 is the perfect destination for a memorable vacation experience. Whether you're looking to soak up the sun on the pristine beaches or explore the local attractions, Breakers 3 is the ideal choice for your next getaway in the United States.

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.

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.

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.

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.

View of the Gulf is a charming lodging establishment located at 7201 Gulf Drive in Holmes Beach, Florida, United States. Situated right on the stunning shores of the Gulf of Mexico, this institution offers guests breathtaking views of the crystal-clear waters and white sandy beaches. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can relax on the private balcony and enjoy the soothing sound of the waves or take a dip in the on-site pool. Whether you're looking for a romantic getaway or a fun-filled family vacation, View of the Gulf is the perfect place to unwind and create lasting memories by the sea.

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.

Lizzie Lu's Island Retreat is a premier real estate and travel agency located at 6000 Marina Drive in Holmes Beach, Florida. Our agency specializes in providing luxurious vacation rentals on the beautiful Anna Maria Island, offering guests a tranquil and unforgettable island experience. With a wide range of properties to choose from, ranging from cozy beachfront cottages to spacious waterfront villas, Lizzie Lu's Island Retreat is dedicated to providing top-notch accommodations and exceptional customer service. Whether you are looking for a relaxing getaway or a fun-filled family vacation, let Lizzie Lu's Island Retreat help you find the perfect rental for your stay 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.

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.

Palm Isle Village Resort is a luxurious real estate and travel agency located at 3201 Gulf Drive in Holmes Beach, Florida, United States. Our resort offers exquisite vacation rentals and properties for sale in the heart of Anna Maria Island. With stunning views of the Gulf of Mexico, our resort provides a peaceful and relaxing escape for travelers looking for a tropical paradise. Our dedicated team of professionals is committed to providing top-notch service and ensuring that every guest has a memorable stay. Whether you are looking for a short-term vacation rental or a permanent residence, Palm Isle Village Resort has the perfect property for you. Experience the beauty of Anna Maria Island with us today!

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.

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.

Wish Upon A Starfish is a real estate and travel agency located at 411 80th Street in Holmes Beach, Florida, United States. This Key West style 3 bedroom home offers a peaceful and relaxing retreat on Anna Maria Island. With vaulted ceilings, an open floor plan, and a private heated pool, this paradise found is perfect for families looking for a beach getaway. The fully equipped kitchen, spacious front deck, and cozy living room provide all the comforts of home. The home is family-friendly, with amenities such as a pack n' play, high chair, and baby gates provided. Children will love the bunk bed room with its own private bathroom, while adults can relax in the Queen size guest bedroom with an adjustable bed.

Tangerine House is a unique institution located at 112 77th Street in Holmes Beach, Florida. As a real estate agency, we specialize in helping clients find their dream homes in the beautiful coastal area of Florida. Our team of experienced agents is dedicated to providing top-notch service and expertise to assist buyers and sellers in navigating the real estate market. In addition to our real estate services, Tangerine House also operates as a travel agency, offering personalized vacation planning services for those looking to explore the stunning beaches and attractions of Florida. Whether you are in search of a permanent residence or a relaxing getaway, Tangerine House is here to help make your dreams a reality. Visit us today to start your journey towards finding the perfect home or planning your next unforgettable vacation.