The 30 Best Relaxing getaways in Holmes Beach, Florida

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Sunset Inn is a charming lodging facility located at 3010 Gulf Drive in Holmes Beach, Florida, United States. This cozy inn offers comfortable and well-appointed rooms, perfect for a relaxing stay by the beach. Guests can enjoy stunning sunsets from the inn's outdoor terrace or take a short walk to the nearby sandy shores. With its convenient location and welcoming atmosphere, Sunset Inn is the ideal choice for a peaceful getaway in beautiful Holmes Beach.

Bamboo Apartments is a beach-front lodging institution located at 3802 Gulf Drive in Holmes Beach, Florida, United States. Our central location on Anna Maria Island is just steps away from the free Island Trolley stop, making it convenient to explore the area. We are within walking distance to a grocery store, drugstore, playground, and various restaurants and shops. Local rental agencies can deliver bikes for those who want to explore the island on two wheels. Our Beach-front Cottage Duplex and Apartments have received 5-star reviews across the board. Guests can read our reviews on social networks and listing sites to learn more about our accommodations. To reach us from Tampa Airport, guests can take I-275 South, through St. Petersburg, and cross the Sunshine Skyway Bridge before heading to Bradenton/Palmetto on US 19. From there, they can head West on SR 64 Manatee Avenue until they reach the Manatee County Beach, where they can turn left on Gulf Drive to find Bamboo Apartments one block south on the right.

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.

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.

Anna Maria Island Coffee Shack is a charming cafe located at 5500 Marina Drive in Holmes Beach, Florida. This cozy spot offers a variety of delicious coffee drinks, freshly baked pastries, and light snacks. The welcoming atmosphere and friendly staff make it the perfect place to relax and enjoy a cup of coffee with friends or grab a quick bite to eat. In addition to their tasty menu items, Anna Maria Island Coffee Shack also features a small store selling unique gifts and souvenirs. Whether you're a local looking for your morning pick-me-up or a tourist exploring the island, this cafe is a must-visit destination.

Anchor Inn is a cozy beachfront bar located at 3007 Gulf Drive in Holmes Beach, Florida. With a laid-back atmosphere and stunning views of the Gulf of Mexico, this institution is the perfect spot to unwind and enjoy a cold drink with friends. Whether you're looking to relax after a day at the beach or catch the game on one of their big screen TVs, Anchor Inn has something for everyone. Come experience the relaxed vibe and friendly service that makes this bar a favorite among locals and visitors alike.

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.

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.

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.

LaPlage 5 is a luxurious beachfront resort located at 6422 Gulf Drive in Holmes Beach, Florida, United States. This stunning property offers guests a perfect blend of relaxation and sophistication, with spacious accommodations and top-notch amenities. Enjoy breathtaking views of the Gulf of Mexico from your private balcony, take a dip in the sparkling pool, or unwind on the pristine sandy beach just steps away. Indulge in gourmet dining options, rejuvenate at the spa, or explore the charming shops and restaurants in the area. LaPlage 5 is the ultimate destination for a memorable beach getaway 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.

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.

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.

Island Vacation Properties is a premier real estate and travel agency located at 3001 Gulf Drive in Holmes Beach, Florida, United States. Specializing in luxury vacation rentals, they offer a wide range of properties on beautiful islands for travelers seeking a relaxing and memorable getaway. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious condo, Island Vacation Properties has the perfect accommodation for your next island vacation. Their team of experienced agents are dedicated to providing exceptional service and helping clients find their dream rental property. Book your island escape with Island Vacation Properties and experience the ultimate vacation experience.

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.

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.

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.

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!

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.