TOP 30 Island getaways in Holmes Beach, Florida

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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.

Anna Maria Island Beach Resort is a charming lodging located at 105 39th Street in Holmes Beach, Florida. Situated on the beautiful Anna Maria Island, this resort offers guests a relaxing and luxurious beachfront experience. With stunning views of the Gulf of Mexico, guests can enjoy pristine white sandy beaches and crystal clear waters right at their doorstep. The resort features comfortable accommodations, a swimming pool, and easy access to a variety of dining and shopping options. Whether you're looking for a romantic getaway or a fun family vacation, Anna Maria Island Beach Resort is the perfect destination for a memorable stay in sunny Florida.

Islands West Resort is a charming lodging establishment located at 3605 Gulf Drive in Holmes Beach, Florida. Situated on the beautiful Gulf Coast of the United States, this resort offers guests a peaceful and relaxing retreat surrounded by stunning ocean views and pristine beaches. The resort features comfortable accommodations, friendly staff, and a range of amenities to ensure a memorable stay for all guests. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, Islands West Resort is the perfect destination for your next trip to Florida.

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.

Anna Maria Beach Resort is a charming lodging located at 6306 Gulf Drive in Holmes Beach, Florida. This beachfront resort offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With stunning views of the Gulf of Mexico, guests can unwind in comfortable accommodations and enjoy the natural beauty of Anna Maria Island. The resort's convenient location allows for easy access to nearby attractions, restaurants, and activities, making it the perfect destination for a memorable beach vacation. Whether you're looking to soak up the sun on the sandy shores or explore the island's quaint shops and galleries, Anna Maria Beach Resort provides the ideal setting for a truly unforgettable getaway.

Haley's at Anna Maria Island Inn is a charming lodging establishment located at 8102 Gulf Drive in Holmes Beach, Florida, United States. Situated on beautiful Anna Maria Island, this cozy inn offers comfortable accommodations and personalized service for a relaxing and enjoyable stay. Guests can enjoy easy access to the beach, as well as nearby shopping, dining, and recreational activities. With its tranquil atmosphere and convenient location, Haley's at Anna Maria Island Inn is the perfect choice for a memorable getaway on 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.

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.

White Sands Beach Resort on Anna Maria Island is a charming lodging option located at 6504 Gulf Drive in Holmes Beach, Florida. This beachfront resort offers guests a peaceful and relaxing retreat with stunning views of the Gulf of Mexico. With comfortable accommodations, a sparkling swimming pool, and easy access to the sandy shores, White Sands Beach Resort is the perfect destination for a beach getaway. Enjoy the laid-back atmosphere and warm hospitality of this beautiful resort on Anna Maria Island.

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.

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.

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.

Anna Maria Island Accommodations is a premier real estate and travel agency located at 3018 Avenue C in Holmes Beach, Florida. Specializing in vacation rentals and property management, our team is dedicated to providing top-notch accommodations and exceptional service to our clients. Whether you are looking for a beachfront villa, a cozy cottage, or a luxury condo, we have a wide range of options to suit your needs. Our knowledgeable staff is here to help you find the perfect vacation rental for your stay on beautiful Anna Maria Island. Contact us today to start planning your dream getaway!

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.

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.

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.

Anna Maria Island is a charming institution located at 5315 Gulf Drive in Holmes Beach, Florida, United States. This unique establishment offers a variety of services including food, real estate agency, restaurant, and travel agency. Whether you are looking to enjoy a delicious meal, find your dream home, or plan a vacation getaway, Anna Maria Island has something for everyone. With its picturesque location and exceptional offerings, it is the perfect destination for those seeking a memorable experience on the beautiful Gulf Coast.

Calico Anna Maria Island is a premier real estate and travel agency located in Holmes Beach, Florida. Situated at the address 4001 5th Avenue, this institution specializes in helping clients find their perfect vacation rental or dream home on the beautiful Anna Maria Island. With a team of knowledgeable and experienced agents, Calico offers personalized services to meet the unique needs of each client. Whether you are looking for a beachfront property, a cozy cottage, or a luxury villa, Calico Anna Maria Island is your go-to destination for all things real estate and travel on this picturesque island.

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!

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 Anna Maria Island Lodging, your perfect getaway destination located in the heart of Holmes Beach, Florida. Nestled at 101 66th Street, our charming accommodations offer a serene escape on the beautiful Anna Maria Island, renowned for its pristine beaches and crystal-clear waters. Our lodging options are designed to provide you with a comfortable and relaxing stay, featuring a variety of amenities to cater to your every need. Whether you're planning a romantic retreat, a family vacation, or a solo adventure, Anna Maria Island Lodging offers the ideal setting for a memorable experience.

The Driftwood Motel is a charming lodging establishment located at 5108 Gulf Drive in Holmes Beach, Florida, United States. Nestled just steps away from the beautiful Gulf Coast, this cozy motel offers comfortable accommodations and a relaxing atmosphere for guests to enjoy. With its convenient location near the beach and local attractions, the Driftwood Motel is the perfect place for a peaceful getaway in paradise. Whether you're looking to relax by the pool or explore the nearby shops and restaurants, this charming motel has everything you need for a memorable stay on Anna Maria Island.

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.

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.

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.