TOP 10 Private island rentals in Holmes Beach, Florida

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 Dolphin Tours is a top-rated travel agency located at 5325 Marina Drive in Holmes Beach, Florida. Offering a variety of boat tours, snorkeling trips, and pontoon rentals, this institution provides the perfect opportunity to explore the beautiful waters surrounding Anna Maria Island. Get up close and personal with bottlenose dolphins as you cruise along pristine beaches and crystal clear waters on a public or private tour. Watch the stunning sunset aboard The Salty Dolphin or embark on a private Island Adventure boat tour to learn about the island's rich history and enjoy the best snorkeling in the area. For those looking for a unique experience, the institution offers private pontoon boat rentals and tours on The Tiki, a 30-foot floating tiki boat with a water slide and Bluetooth sound system. Customize your cruise to include sandbar hopping, swimming, snorkeling, or wildlife watching. With experienced captains providing guided dolphin eco-tours, sunset tours, and trips to Egmont Key, you're sure to have an unforgettable experience on the water. Don't miss out on the opportunity to see dolphins, manatees, sea turtles, and other tropical wildlife up close. Book a tour with Anna Maria Island Dolphin Tours today for a fun and educational adventure on the water!

Island Hoppers Boat Tours offers private boat tours and dolphin tours on Anna Maria Island, located at 752 Manatee Avenue West in Holmes Beach, Florida. Embark on a memorable adventure with experienced guides who will take you on a journey to discover the beauty of the Gulf Coast. Enjoy the stunning views and wildlife sightings as you cruise through the crystal-clear waters. Whether you're looking for a relaxing day on the water or an exciting dolphin watching experience, Island Hoppers Boat Tours has something for everyone. Book your tour today and create lasting memories with your loved ones.

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.

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.

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.

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.

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.

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.

AMI Escapes Boat Tours is located at 6398 Marina Way in Holmes Beach, Florida. It is Anna Maria Island's most popular adventure boat tour, offering private and all-inclusive experiences customized for each group. Guests have the opportunity to visit secluded islands, beaches, and sandbars such as Egmont Key, Passage Key, Jewfish Key, and Beer Can Island. The tours include amenities such as paddle boards, snorkeling gear, fishing poles, and underwater scooters, with no set schedule so guests can enjoy the experience for as long as they desire. In addition to island hopping, the tours also offer stops at local restaurants and opportunities for swimming, snorkeling, and paddle boarding. The institution also offers dolphin tours, snorkeling trips with underwater scooters, and sunset cruises with a premium Bluetooth sound system. With comfortable boats, complimentary water and soft drinks, and the option to bring adult beverages on board, AMI Escapes Boat Tours provides a luxurious and customizable boating experience for visitors to Anna Maria Island, Longboat Key, and Bradenton Beach.

Egmont Key Adventures is a unique institution located at 5500 Marina Drive in Holmes Beach, Florida. This establishment is a combination of a clothing store, store, and travel agency, offering a wide range of products and services for outdoor enthusiasts and travelers. From stylish apparel and gear for your next adventure to booking exciting travel experiences, Egmont Key Adventures has everything you need to make your trip unforgettable. Visit us today and start planning your next great escape!

Crysten's AMI Boat Tours, located at 3230 East Bay Drive in Holmes Beach, Florida, offers an unparalleled private boat tour experience. Our all-inclusive boat rentals take you along the crystal clear waters of Anna Maria Island, providing breathtaking sunset cruises, vibrant snorkeling expeditions, enchanting water wildlife tours, and all-inclusive sandbar experiences. Departing daily from Holmes Beach and Bradenton Beach, we guarantee unforgettable moments on the water. Our snorkeling trips include gear and allow you to explore the underwater wonders of AMI, from exotic fish to baby octopuses and seahorses. Perfect for all ages, this adventure is truly unforgettable. Our full day aquatic adventure charter offers endless fun in the sun, with customized experiences available upon booking.

Welcome to Villa #1 Sailfish by AMI Locals, your perfect getaway on beautiful Anna Maria Island. Nestled at 3605 Gulf Drive, Holmes Beach, Florida, this charming two-bedroom, two-bath villa is a mere two-minute stroll from the pristine Gulf of Mexico beaches. Part of the picturesque Island West Resort, Villa #1 Sailfish offers a delightful blend of comfort and convenience, ideal for families, couples, and friends traveling together. Highlights of Villa #1 Sailfish include: