TOP 30 Best Island paradise vacation rentals in Holmes Beach, Florida

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.

Welcome to Coconut Rentals - Golf Cart Rentals Anna Maria Island, your premier destination for exploring the beautiful Anna Maria Island with ease and style. Conveniently located at 5338 Gulf Drive, Holmes Beach, Florida, our business offers a unique blend of car rental services and local charm, making us a must-visit attraction for both tourists and residents alike. At Coconut Rentals, we specialize in providing top-quality golf cart rentals, perfect for navigating the island's scenic roads and discovering its hidden gems. Our fleet of modern and well-maintained golf carts ensures a comfortable and enjoyable ride, allowing you to soak in the breathtaking coastal views and vibrant island life.

Harbor Lane Court offers luxurious vacation rentals on the beautiful Anna Maria Island in Florida. Located at 4509 Gulf Drive in Holmes Beach, this lodging institution provides guests with a serene and comfortable stay just steps away from the stunning Gulf of Mexico. Enjoy spacious accommodations, modern amenities, and a prime location for exploring the island's charming shops, restaurants, and attractions. Immerse yourself in the laid-back island lifestyle and create unforgettable memories at Harbor Lane Court.

Welcome to Holmes Beach, a premier tourist attraction located at 4000 Gulf Drive, Holmes Beach, Florida. Nestled on the stunning Anna Maria Island, our location offers an idyllic escape for visitors seeking sun, sand, and sea. Holmes Beach is renowned for its pristine beaches, crystal-clear waters, and breathtaking sunsets, making it a perfect destination for relaxation and recreation. Whether you're looking to unwind on the soft sandy shores, explore the vibrant marine life, or indulge in water sports, Holmes Beach has something for everyone. Our area is rich with local charm, featuring a variety of dining options, boutique shopping, and cultural experiences that capture the essence of Florida's Gulf Coast.

Umbrella Beach Resort is a charming lodging establishment located at 3805 Gulf Drive in Holmes Beach, Florida, United States. Nestled along the pristine shores of the Gulf of Mexico, this resort offers guests a tranquil and relaxing beachfront getaway. With spacious and well-appointed accommodations, stunning ocean views, and a range of amenities including a pool, beach access, and on-site dining options, Umbrella Beach Resort is the perfect destination for those seeking a peaceful escape by the sea. Whether you're looking to unwind on the beach, explore the local attractions, or simply soak up the sun, this resort provides a welcoming and comfortable retreat for all travelers.

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.

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.

Coconuts Beach Resort is a charming lodging destination located at 100 73rd Street in Holmes Beach, Florida, United States. Nestled along the beautiful shores of the Gulf of Mexico, this resort offers guests a relaxing and tropical getaway. With cozy accommodations, stunning ocean views, and a laid-back atmosphere, Coconuts Beach Resort is the perfect place to unwind and enjoy a peaceful beach vacation. Whether you're looking to soak up the sun on the sandy shores, take a dip in the crystal-clear waters, or explore the nearby attractions, this resort has everything you need for a memorable stay. Come experience the beauty and tranquility of Coconuts Beach Resort on your next trip to Florida.

Welcome to Holmes Beach, Florida, a stunning natural feature located at 310 58th Street in the heart of Holmes Beach, Florida. Nestled on the beautiful Anna Maria Island, this picturesque location offers a serene escape for nature lovers and beachgoers alike. With its pristine white sandy beaches, crystal-clear turquoise waters, and breathtaking sunsets, Holmes Beach is the perfect destination for relaxation and outdoor activities. Whether you're looking to sunbathe, swim, fish, or explore the diverse marine life, this natural paradise provides an unforgettable experience for visitors of all ages. Embrace the tranquil atmosphere and discover the charm and beauty that make Holmes Beach a true gem on Florida's Gulf Coast. Come visit us and create memories that will last a lifetime.

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.

Mike Norman Realty on Anna Maria Island is a reputable real estate and travel agency located at 3101 Gulf Drive in Holmes Beach, Florida. Specializing in vacation rentals, property sales, and property management services, this institution is dedicated to helping clients find their perfect slice of paradise on the stunning Anna Maria Island. With a team of experienced agents and a deep knowledge of the local market, Mike Norman Realty offers personalized assistance and top-notch customer service. Whether you are looking to buy, sell, or rent a property on Anna Maria Island, this agency is your go-to destination for all your real estate needs.

Beach Life At The Pointe Apartment 2 is a charming accommodation located at 105 36th Street in Holmes Beach, Florida. This cozy apartment offers a relaxing and comfortable stay just steps away from the beautiful beaches of the Gulf Coast. With a fully equipped kitchen, spacious living area, and private balcony, guests can enjoy all the comforts of home while soaking up the sun and sea breeze. Whether you're looking to unwind on the beach, explore the local shops and restaurants, or simply relax in the tranquility of the island, Beach Life At The Pointe Apartment 2 is the perfect retreat for your beach getaway.

Mermaids Crossing Beach Vacation Rental on Anna Maria Island in Florida offers stunning vacation rental properties for visitors looking to enjoy a relaxing beach getaway. Situated at 207B 69th Street in Holmes Beach, this real estate and travel agency specializes in providing luxurious accommodations with breathtaking views of the Gulf of Mexico. Whether you're seeking a romantic escape or a fun-filled family vacation, Mermaids Crossing has the perfect rental for you. Experience the beauty of Anna Maria Island and make unforgettable memories at Mermaids Crossing Beach Vacation Rental.

AnnaMaria Island Beach Cottage is a charming and cozy beachfront property located at 2813 Avenue East in Holmes Beach, Florida. This beautiful cottage is managed by a reputable real estate and travel agency, offering guests a relaxing and luxurious vacation experience. With stunning ocean views, modern amenities, and a prime location just steps away from the sandy shores of AnnaMaria Island, this cottage is the perfect getaway for those looking to unwind and enjoy the beauty of the Gulf Coast. Whether you're seeking a romantic retreat, a family vacation, or a solo adventure, AnnaMaria Island Beach Cottage is the ideal destination for your next beach getaway.

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.

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.

Anna Cabana Resort by Island Vacation Properties is a charming lodging located at 3709 Gulf Drive in Holmes Beach, Florida, United States. This resort offers a relaxing and comfortable stay in a tropical paradise setting. Guests can enjoy spacious and well-appointed accommodations, a sparkling swimming pool, and easy access to the beautiful Gulf of Mexico beaches. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Anna Cabana Resort is the perfect destination. Experience the laid-back island lifestyle and create unforgettable memories at this wonderful resort.

Island Retreat Vacations is a premier real estate and travel agency located at 5354 Gulf Drive in Holmes Beach, Florida, United States. Specializing in luxury vacation rentals on beautiful islands, our agency offers a wide range of accommodations to suit every traveler's needs. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious condo, we have the perfect retreat for your next getaway. Our team of experienced agents is dedicated to providing exceptional service and ensuring that your vacation is unforgettable. Book your island retreat with us today and experience the ultimate in relaxation and luxury.

Beach Dreams is a travel agency located at 207 66th Street in Holmes Beach, Florida. Specializing in creating unforgettable beach vacations, Beach Dreams offers a wide range of services to help you plan the perfect getaway. From booking accommodations to arranging activities and excursions, their team of experienced travel agents are dedicated to making your dream beach vacation a reality. Whether you're looking for a relaxing beach retreat or an action-packed adventure by the sea, Beach Dreams is your go-to destination for all things beach-related. Start planning your next beach vacation with Beach Dreams today!

GulfCart Fishing Charters, located in Cortez, Florida, is a top tourist attraction and travel agency offering private fishing charters in the Anna Maria Island, Bradenton, Holmes Beach, Longboat Key, and Cortez Beach areas. Captain Eric Chaignet, with over twenty years of experience fishing the local waters, provides a first-hand perspective on where the fish are biting. Anglers can expect to catch a variety of fish such as Snapper, Grouper, Shark, Redfish, Mackerel, Tarpon, Snook, and Trout on their inshore and offshore fishing excursions. Customers rave about the 5 star experience with GulfCart Charters, praising Captain Eric's knowledge and expertise. Whether it's your first time fishing or you're a seasoned angler, Captain Eric ensures a fun-filled day on the water. With access to some of the most bountiful fishing destinations in Holmes Beach and Cortez Beach, GulfCart Charters promises an unforgettable fishing experience.

Fun Boat Tours is a premier travel agency located at 5501 Marina Drive in Holmes Beach, Florida. We offer exciting and memorable boat tours for all ages to explore the beautiful waters of the Gulf Coast. Our experienced guides will take you on an adventure to see dolphins, manatees, and other marine life up close. Whether you're looking for a relaxing sunset cruise or a thrilling snorkeling excursion, Fun Boat Tours has something for everyone. Book your next aquatic adventure with us and create unforgettable memories on the water.

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.

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.

AMI Locals is a premier real estate and travel agency located in Holmes Beach, Florida. Our team of dedicated professionals is committed to providing top-notch service in helping clients find their perfect vacation rental or dream home on Anna Maria Island. With a focus on personalized attention and local expertise, we strive to make the process of buying, selling, or renting property as seamless as possible. Whether you are looking for a beachfront villa or a cozy cottage, AMI Locals has the resources and knowledge to make your real estate dreams a reality. Contact us today at 3018 Avenue C to start your journey towards finding the perfect property in paradise.

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.

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.

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.

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!

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.

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.