TOP 10 Vacation cottage rentals in Holmes Beach, Florida

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A Paradise Vacation Rentals is a premier real estate and travel agency located at 5201 Gulf Drive in Holmes Beach, Florida. Our agency specializes in providing luxurious vacation rental properties for those seeking a paradise getaway on the beautiful Gulf Coast of Florida. With a wide selection of beachfront condos, waterfront villas, and cozy cottages, we offer the perfect accommodations for every traveler. Our dedicated team of professionals is committed to providing exceptional service and ensuring that your vacation experience is nothing short of extraordinary. Book your dream vacation with A Paradise Vacation Rentals and make unforgettable memories in paradise.

Island Real Estate Vacations on Anna Maria Island is a premier real estate and travel agency located at 3909 East Bay Drive in Holmes Beach, Florida. With a wide range of vacation rental properties available, they provide visitors with the perfect accommodations to enjoy all that this beautiful island has to offer. Whether you're looking for a beachfront villa, a cozy cottage, or a luxurious condo, Island Real Estate Vacations has something for everyone. Their knowledgeable staff is dedicated to ensuring a seamless and memorable vacation experience for all guests. Experience the beauty and tranquility of Anna Maria Island with Island Real Estate Vacations.

Four Beach Lovers is a charming lodging establishment located at 2908 Avenue East in the picturesque town of Holmes Beach, Florida. This cozy retreat is perfect for those who have a deep love for the beach and all it has to offer. With comfortable accommodations and a welcoming atmosphere, Four Beach Lovers is the ideal spot for a relaxing getaway by the sea. Whether you're looking to soak up the sun, take a leisurely stroll along the shore, or simply unwind with a good book, this institution is the perfect place to indulge your love for the beach. Come experience the beauty and tranquility of Holmes Beach at Four Beach Lovers.

Mello on the Beach is a charming lodging and real estate agency located at 105 39th Street in Holmes Beach, Florida. Situated just steps away from the beautiful sandy beaches of the Gulf Coast, this institution offers a variety of vacation rentals and properties for sale in the area. Whether you're looking for a relaxing beach getaway or considering investing in a piece of paradise, Mello on the Beach has everything you need to make your dream a reality. Experience the best of Florida living at Mello on the Beach.

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.

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.

Salty Mermaid Real Estate & Vacation Rentals is a premier real estate agency and travel agency located at 5306 Holmes Boulevard in Holmes Beach, Florida. Specializing in beachfront properties and luxury vacation rentals, Salty Mermaid offers a wide range of options for those looking to buy, sell, or rent in this beautiful coastal community. With a team of experienced agents and personalized service, Salty Mermaid is your go-to destination for all your real estate and vacation needs in Florida.

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.

Holmes Beach Latitude Attitude is a premier real estate and travel agency located at 4001 Gulf Drive in the charming town of Holmes Beach, Florida. Our team of experienced professionals are dedicated to helping clients find their dream vacation rental or investment property in this beautiful coastal community. Whether you're looking to buy, sell, or rent, we have the expertise and resources to make your real estate experience seamless and successful. Additionally, our travel agency services can help you plan the perfect getaway to this idyllic beach town. Let Holmes Beach Latitude Attitude guide you to the perfect property or vacation rental that suits your needs and budget.

Beach House Real Estate is a premier institution located at 5309 Gulf Drive in Holmes Beach, Florida, United States. Specializing in lodging, real estate, and travel services, Beach House Real Estate offers a wide range of beachfront properties for sale or rent. Whether you are looking for a vacation rental, a new home by the beach, or assistance with planning your next travel adventure, our experienced team is here to help. With a prime location on the Gulf Coast, Beach House Real Estate is your one-stop destination for all your beachfront property and travel needs.

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.

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!

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.

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.

SeaBreeze Vacation LLC is a full-service real estate and travel agency located at 5372 Gulf Drive in Holmes Beach, Florida, United States. Our Reservation Specialists are available 9 AM-Midnight EST, 7 days a week to help you find the perfect vacation home on Anna Maria Island. We offer a variety of homes for couples, families, and large groups, with amenities such as pet-friendly options, properties with docks, and golf cart rentals for easy island exploration. When you book directly with SeaBreeze Vacation, you can enjoy the best rates with no hidden fees. Our flexible cancellation policy allows you to cancel bookings up to 14 days before check-in and receive a refund. Our staff, who are either island locals or longtime transplants, are always available to assist with any needs or maintenance during your stay.

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.

Vacation Cottages Anna Maria Island offers charming and comfortable cottage rentals in the picturesque Holmes Beach, Florida. Located at 206 Haverkos Court, our real estate and travel agency specializes in providing guests with the perfect vacation getaway. Whether you're looking for a romantic retreat or a family-friendly escape, our cottages are the ideal choice. With easy access to the stunning Anna Maria Island beaches and a variety of local attractions, our rentals provide the perfect home base for your next vacation. Book your stay with us today and experience the beauty and relaxation of Holmes Beach!

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.

Buddy's Beach House is a charming vacation rental located on Anna Maria Island in Holmes Beach, Florida. This beachy chic property is just 2 blocks away from the ocean, making it the perfect getaway for those looking to relax and unwind by the water. The house sleeps 4 guests and features two bedrooms with queen size beds, luxurious linens, and comfortable mattresses. The property also includes 1.5 bathrooms and a fabulous outdoor shower for rinsing off after a day at the beach.

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!

Beach Retreats Vacation Rentals & Property Management is a premier real estate and travel agency located at 5306 Holmes Boulevard in beautiful Holmes Beach, Florida. Our agency specializes in providing luxurious vacation rentals and top-notch property management services for discerning clients looking to experience the ultimate beach getaway. Whether you are seeking a cozy beachfront cottage or a spacious waterfront villa, our team of experts is dedicated to helping you find the perfect accommodations for your dream vacation. With a focus on exceptional customer service and attention to detail, Beach Retreats Vacation Rentals & Property Management is committed to ensuring that your stay in Holmes Beach is unforgettable. Contact us today to start planning your next beach retreat!

My Big Fat Beach House is a real estate and travel agency located at 301 72nd Street in Holmes Beach, Florida. Our family-owned business offers the perfect backdrop for creating unforgettable memories with your loved ones. Located on Anna Maria Island, our beach house is the ideal vacation destination with warm gulf waters and white sand beaches just steps away. You can enjoy the comforts of our home while we are away, creating memories that will last a lifetime.

Tidal Daze Vacation Home is a charming real estate and travel agency located at 203 72nd Street in Holmes Beach, Florida, United States. Our agency specializes in providing luxurious vacation homes for rent in the beautiful coastal town of Holmes Beach. With stunning views of the ocean and easy access to the beach, Tidal Daze Vacation Home offers the perfect retreat for those looking to relax and unwind. Whether you're planning a family vacation or a romantic getaway, our friendly staff is dedicated to helping you find the perfect rental property to suit your needs. Book your dream vacation with Tidal Daze Vacation Home today and experience the ultimate beachfront escape.

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.

Welcome to AMI Beaches Real Estate, your trusted partner in finding your dream home or investment property on the stunning Anna Maria Island. Conveniently located at 5309 Gulf Drive, Holmes Beach, Florida, our dedicated team of real estate professionals is committed to providing personalized and comprehensive services tailored to meet your unique needs. At AMI Beaches Real Estate, we specialize in a wide range of real estate services, including residential sales, vacation rentals, and investment opportunities. Whether you are looking to buy, sell, or rent, our extensive knowledge of the local market and unwavering dedication to client satisfaction ensures a seamless and rewarding experience.

MI Happy Place Island Resort is a charming lodging located at 301 42nd Street, Holmes Beach, Florida, United States. Our resort offers a full size pool that is heated and chilled as needed to ensure a great vacation experience. Whether you are planning a family reunion, a romantic beach wedding, a corporate function, or just a fun getaway, our resort is the ideal setting for all occasions. The recently renovated and remodeled units at MI Happy Place Island Resort offer casual elegance and a beachy, fun decor that welcomes you to relax in style. Each unit comes with a full kitchen, luxurious bath linens, and incredibly comfortable beds. You can choose to spend your days lounging by the pool and having a barbecue, both of which are included with your stay.

Angelinos Sea Lodge is a charming lodging establishment located at 2818 Avenue East in Holmes Beach, Florida. This institution offers cozy accommodations with stunning ocean views, perfect for a relaxing beach getaway. In addition to providing lodging services, Angelinos Sea Lodge also operates as a real estate agency, helping guests find their dream beachfront property in the area. As a travel agency, they can assist visitors with planning their vacation, from booking flights to organizing excursions and activities. Whether you're looking for a place to stay or seeking assistance in purchasing a beachfront property, Angelinos Sea Lodge has you covered.

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.