Vacation Rentals

Escape to Your Exclusive Tropical Retreat! Indulge in the privacy of your own backyard oasis, complete with a sprawling pool and a dedicated Beach Volleyball Court. Open the back gate and find yourself steps away from the pristine Gulf Beaches. This ground-floor haven offers unparalleled convenience, featuring a brand-new kitchen, four modern bathrooms, four inviting bedrooms, and the added luxury of two outdoor showers. Plus, a delightful array of toys and amenities awaits your enjoyment, including bikes, paddle boards, kayaks for exploration. Bring your furry companions along, as pre-approved pets are warmly welcomed to bask in our newly manicured, clean turf. Whether you're barbecuing on the grill, or lounging on the patio to catch stunning sunsets or sunrises, this is the perfect setting for your getaway. Nestled on the sought-after North End of Anna Maria Island, where playful dolphins dance in the waves and year-round award-winning sunsets paint the sky, you'll be captivated by the beauty that surrounds you. Sink your toes into the sugar sand beach, explore charming local shops, and savor the flavors of exceptional restaurants. A short bike or golf cart ride takes you to Pine Ave, where shopping and an array of award-winning dining options await. Whether you're in the mood for retail therapy or a gourmet meal, you'll find it all just moments away. Embark on an unforgettable journey to our private Fanta-Sea – a haven where relaxation and adventure unite seamlessly. Secure your spot now and embark on the vacation of a lifetime. Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver.  Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Discover Serendipity: Your Pet-Friendly Beachfront Haven on Anna Maria Island Beachfront Bliss Awaits You Indulge in the enchantment of beachfront bliss at Serendipity, an exceptional 4-bedroom home perfectly positioned on the coveted North End of Anna Maria Island. This tranquil escape beckons you to unwind and relish in a symphony of swimming, relaxation, and endless memories. Immerse yourself in captivating sunsets from your expansive deck or venture just steps away to the world-renowned Bean Point beach. With the added convenience of an elevator connecting all floors, your comfort is our top priority. Elegance Meets Comfort: Floor Plan & Beds Serendipity presents a floor plan designed for both elegance and comfort: Master Bedroom: King Bed with En-suite Bathroom Bedroom 2: King Bed Bedroom 3: King Bed Bedroom 4: King Bed Hall Bathroom: Tub/Shower Combination Half Bathroom: Conveniently Accessible from the Hall Ground Floor: A Welcoming Half Bathroom with Outdoor Shower Beachfront Hot Tub Imagine unwinding beneath the starlit sky in your own beachfront hot tub, soothing your senses and enhancing the magic of your stay. A Glimpse of Paradise: No Pool Yet, But a New One Is in the Works While the allure of a private pool is on the horizon, we're thrilled to share that plans are in motion for the creation of a brand-new pool, poised to elevate your future stays to new heights. In the meantime, embrace the direct beach access and the soothing embrace of the ocean. Endless Adventures Await Our commitment to delivering an unforgettable experience extends to an array of amenities awaiting your discovery. Embark on island explorations with the provided 4 adult bikes, navigate the tranquil waters with 2 stand-up paddleboards (SUPs), or set out on tandem excursions with the included kayak. (Signed Waivers for All Adults Required) Pet-Friendly Paradise We understand that your furry companions are part of the family. Serendipity warmly welcomes pre-approved pets to share in the serenity with you. A signed pet agreement and a pet fee ensure the comfort and cleanliness of all guests. Secure Your Slice of Paradise Serendipity isn't just a vacation rental; it's an invitation to experience the quintessential Anna Maria Island lifestyle. From the allure of sunsets to the caress of warm sand, create lasting memories in this idyllic haven. Book Your Escape Today Don't miss out on this unparalleled opportunity. Reserve your stay now and embrace the serenity that awaits, for both you and your cherished companions. Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Welcome to Mintfish, your calm, canal front oasis. This getaway home marries natural elements with luxury to create the perfect vacation spot for you, your friends, and your family (even the furry members!). The ground-level, single-floor home makes relaxation accessible for anyone and everyone. Recent remodels have brought the 4 bedrooms and 4 bathrooms into pristine condition… The only thing missing is you.  Nestled in the north end of Anna Maria Island, Mintfish provides close proximity to Gulf beaches, beautiful sights, and perfect weather. However, most of its magic lies on its own property. You can take in the views of the island from the comfort of your own private, heated pool. When you’re done with the pool, you can take a stroll down the dock to take in the sunrise or sunset. When mealtime rolls around, the chef of the group can fire up the outdoor gas grill for a glorious outdoor dinner. Or, the group can jump into a rented golf cart and head to Anna Maria City Pier or Pine Avenue, where you’ll find award-winning restaurants and bars. If you’d like to take an active turn on your vacation, you can explore the island and the surrounding water via kayak or paddle board. Take a dive into the water and you just might be lucky enough to catch sight of a manatee or a dolphin enjoying the sea. After a day full of activity, you can unwind and relax your muscles in the hot tub on the property. However you choose to spend your vacation, the Mintfish is sure to provide everything you need for a serene oasis in the heart of charming Anna Maria Island.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Welcome to your Gulfside, bohemian escape! Serendipity Gulf’s minimalistic, peaceful approach to decor strips away all the unnecessary to leave you with a serene oasis out to the beach that lies just beyond the back door. The clean, white decor within the home leaves plenty of opportunity for your eyes to travel out the back sliding glass doors to the ocean just beyond. Your group can snuggle into the dining nook for a cozy breakfast before heading out the back door to the beach. At the end of the day, all you have to do is make the quick walk back up to the house to take a quick shower, grab a glass of wine, and settle into either the lanai chairs or the brand-new hot tub in the evening. As the sun melts over the island, your worries will melt away, too. As night falls, your group will retreat into their own space in the 3 bedrooms within the house or the 1/1 separate cottage.  Located in the north end of Anna Maria Island, this home offers not only a tranquil ambiance but proximity to many local gems on the island. With the house comes paddle boards, kayaks, and bikes for you and your group to enjoy. Wheel a kayak down to the beach and paddle out in hopes of catching sight of a dolphin or two, or take out the paddle board for a quick morning workout on the ocean. If you aren’t feeling like firing up the gas BBQ that the house has, load up into the bikes and head down to Pine Avenue to enjoy award-winning local restaurants with your group.  From sunrise to sunset, the tranquility that Anna Maria Island has to offer is unmatched. There’s no better place to soak it all in than the bohemian chic Serendipity Gulf house. Stripping away all the extras and leaving you with just the peace of a beautiful home and the picturesque ocean, it’s impossible to not have a dream like vacation.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Luxury and the beach intersect at a point titled Serendipity Deux. This gorgeous 4 bedroom home offers all the allure of an extravagantly decorated space while giving you premium beach access and an ideal location. The Master Suite is located on the first level and comes outfitted with a king bed, tub and shower, and plush decor. On the home’s second level, you’ll find the remaining 3 bedrooms, each with king beds, as well. An elevator provides access throughout the home, and most of the main features are located on the first level - including a family room, dining room, and kitchen with high-end, luxurious finishes.  While the house itself carries a high level of magic, the experience doesn’t end there. When you check into paradise at Serendipity Deux, you’ll also be provided access to bikes, a kayak, and paddle boards. In addition to these possible activities, the beach itself is mere footsteps outside of the home. Everything about the home provides convenience packed up and tied with a luxurious bow.  Your group would be remiss to come to Anna Maria Island and not fully explore. When you’ve soaked up the home’s features, you can venture out to Rod & Reel Pier, Pine Avenue, or Bean Point. The 7-mile-long island holds countless hidden gems and local spots that are sure to make you feel right at home. When you’re sure that you’ve experienced all the charm the island has to offer, your group can come back and sink back into the lap of luxury at Serendipity Deux.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Welcome to paradise! This beachfront blends modernity with relaxation to give your group a heavenly experience. Located in a prime location on the North End of Anna Maria Island, Cloud 9 has everything that your group needs for a perfect vacation. Each of the 4 bedrooms is professionally decorated and complete with King Beds, TVs, and En-Suite Bathrooms to make sure that your comfort is the top priority.  Ready for dinner? The Chef’s Kitchen has a 48-inch gas range ready to create mouthwatering meals. Alternatively, there is a Gas BBQ on the lower pool deck for the evenings that are too nice to not grill out. Pop open a bottle of wine from the wine cooler and enjoy it as you watch the sunset over the ocean on your private covered porch.  Your group will have easy beach access and a simple stroll to Bean Point in this private, residential neighborhood. After spending your day at the beach, come back and enjoy a movie on any one of the TVs in the space. If you’re still itching for more activity, your group can take out the bikes, kayaks, or paddle boards that all come included with Cloud 9. You’ll never have a worry, as we or our assistant are available to assist you 24/7. All you have to do is show up and find yourself on Cloud 9. Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver.  Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Welcome to your very own piece of luxury! Floor-to-ceiling windows, a backyard oasis, and the beach across the street. What more could you want? With four bedrooms, two bathrooms, and an elevator to the main level of the house, relaxation is accessible for everyone. While you and your party are inside the house, you can cook a delicious meal while gazing out the windows at a beautiful sky view. After dinner, grab a drink and cozy up around the stunning indoor fireplace as you take in the statement pieces that fill the home. The ambiance doesn’t stop indoors, though.  When you walk out into the backyard, you will be transported into your own zen oasis. A lush variety of trees provide shade for you and your group as you gather around in the Adirondack chairs. And just across the street… the beach awaits. Come with as little as yourself and a towel, or bring one of the available paddleboards to explore the ocean. Itching to explore more? Grab one of the bikes and take a ride around Anna Maria Island’s 7 miles.  SKY offers you a prime location for all that Anna Maria Island has to offer. During your stay, you can explore the pier and drive down to Pine Avenue, where award-winning restaurants and local shops wait for you. When you’re done exploring, though, you’ll have the delight of coming back home to SKY - your dream luxury retreat.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Beachfront paradise awaits you at the TripleTail. Located in a prime location - just one block from Pine Avenue and the City Pier, the 4 bed/4 bath home offers everything you need for the perfect vacation. On the ground floor, you’ll find a beachfront king bedroom, along with a second king bedroom, kitchen, dining room, and family room. Upstairs, two more king bedrooms and bathrooms, as well as a sitting area, ensure the comfort of your entire group for the length of your vacation.  The best part, however, begins when you step outdoors. The back deck gives perfect views of the water, where you can watch dolphins frolic and the waves roll in. Take a dip in your private pool or grab a drink and unwind in the hot tub that faces the ocean. On top of all of this, the beach itself is just steps away once you step out the door. In no time, you’ll find yourself immersed in the beauty of the Gulf beach’s white sands and blue water. The house also comes equipped with bikes, a kayak, and paddle boards to make sure that nothing stands in the way of you enjoying your trip. Land and sea are both explorable to you with these modes of transportation, which is perfect since Anna Maria holds charm in every inch of its 7-mile strip. The quaint magic that the island holds will captivate you, and you just might find yourself never wanting to leave TripleTail.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Welcome to your vacation home that has been kissed by the Florida sun. When you and your group check into Sunkissed, you’ll be taken aback by the views of the ocean, the private pool, and the sunset melting into the skyline. With 2 large bedrooms and two chairs that convert into twin beds, your family will be cozy and comfortable for your entire vacation here on Anna Maria Island.  The open floor plan gives you an uninhibited view of Egmont Key and the Skyway Bridge through the large picture windows at the back of the house. When you step out into the front yard, you’ll step into a lush landscape of green, tropical plants and your very own private, heated pool. And even though that alone would make for an excellent vacation, the magic doesn’t stop there. Just out the back of the house is a beautiful view and beach access for you and your group.  SunKissed has everything you could possibly need for a dream-worthy trip, from a BBQ grill to bikes, a kayak, and paddle boards. Take them out for a spin to explore the island - both land and sea. As you kayak through the water, you may be lucky enough to catch sight of a pod of dolphins or local wildlife. You can explore the expanse of the island with a rented golf cart, taking it to Rod & Reel Pier or Pine Avenue. Whatever you choose to make your vacation count, SunKissed makes it available at your fingertips.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Waterfront 3/3 on the north end of Anna Maria Island. Tropical Paradise, hidden gem with an elevator, dock and peaceful water views. The waterway is locally named the "Fish Highway". Take the elevator up to a secret lookout tower with views of Tampa Bay and the Canal. One block from Pine Avenue and 2 houses from the bayside beach. Bikes, SUP, Kayak included as well as a 4 passenger golf cart. (Signed Waivers Required for all Amenities. Golf Cart limited to adults 25+ with a valid DL, Auto Insurance and signed waiver) There are two king bedrooms. One bedroom has a connected shower bathroom. The other bathroom is accessible from the hall and has a tub. The third bedroom is on the ground floor and has two twin beds and a half bathroom. Pre-approved pets are welcome. There is a pet fee and a pet agreement required

LimeFish’s luxurious, bohemian aura makes it the perfect vacation spot. The open floor plan features 3 remodeled bedrooms, and 4 bathrooms, and is the perfect accommodation for your group. With a sleeper sofa in the living room and bunks in one of the bedrooms, you can fill the house with your family and friends for the beach trip of a lifetime.  After you check into the beautiful accommodations, the world is your oyster. Make your way out back to the covered outdoor kitchen and fire up the outdoor gas grill. You can set the tables for the ideal sunset dinner and settle in for a dreamy sunset. If cooking isn’t calling your name, load up into a rented golf cart and make your way to Pine Avenue, where you’ll find countless award-winning, local spots.   During your stay, you can park yourself on a beach chair and soak in the sun all day, every day. You can watch the dolphins jump in the waves from the deck as the tide goes in and out. Take a dip in the private pool before lounging under the sea grape trees for an afternoon nap. Or you can take your vacation more actively, with access to kayaks and stand-up paddleboards. The only thing left to do is book your LimeFish paradise vacation! Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Come seize the day at Sea La Vie, located on the north end of gorgeous Anna Maria Island. This home welcomes you and your group with unique finishes and handpicked furniture to make sure that your vacation stands out among all the others. Complete with 3 bedrooms and 3.5 bathrooms, Sea La Vie has room for your entire party to relax comfortably. On the main level, you’ll find two guest suites, a living room, a dining area, a powder bath, and a laundry room to make sure that your vacation is as convenient as possible. On the third level, you’ll be swept into paradise by the master suite’s natural light, luxurious bathroom, and private covered terrace inviting you to take in all the sights of the island. However, the master suite isn’t the only one with a view. Off the back of the house, your group will fall in love with the spacious, screened-in lanai that looks down on the resort-style pool area. If those views aren’t enough for you, simply take the stairs up to the 360-degree view on the rooftop deck, where you can breathe in the sunrise and sunset over the Gulf and the bay.  When you’re finally able to pry yourself away from the views and the luxury of Sea La Vie itself, you’ll find yourself amazed at the endless possibilities for activity. At the house, you’ll find a pool that rivals the best resort pools. The saltwater pool features not one, not two, but three waterfall features and a spa. And of course, if you’re coming to Anna Maria Island, you likely are coming for the beach. Luckily for your group, beach access is mere steps away from your front door. Grab one of the paddleboards or the kayak and take it out to the beach to explore, or grab some bikes and take a bike ride alongside the beach.  The fun doesn’t stop there, though. Your group can pile into a rented golf cart and explore the island at any point during your vacation. While you’re staying at the Sea La Vie, you’ll be just minutes away from some of the best gems the island has to offer. Make your way to Pine Avenue and enjoy some of the unique and delicious restaurants that line the street, or head to Rod & Reel Pier. The good news for your group is that, wherever you are, Anna Maria Island is full of both popular and hidden gems to explore. There is no better home base for your explorations than Sea La Vie, so start making your plans today.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Welcome to the coveted Marina Drive! Located in the heart of Holmes Beach on Anna Maria Island, Paradise Point offers a dream beach vacation complete with unrivaled views, private balconies, and just a short walk to the beach. Bring your friends and family to stay in this 3 bedroom oasis in a prime location on the island. With newer stainless steel appliances, balconies that offer a peek into canal basins and wildlife views, and a brand new pool, Paradise Point gives a uniquely homey and residential experience of the gorgeous Anna Maria Island. As your group settles into the home, you can take a cup of coffee or glass of wine out onto one of the multiple balconies that are attached to the house - whether it’s the private master suite balcony or the back balcony that overlooks the pool. The master suite holds two walk-in closets, a walk-in shower, separate sinks, and a soaking tub to relax in at the end of a long day at the beach.  During the day, your party doesn’t even have to leave the residence to soak in the warm Florida sun. Take a dip in the new pool while surrounded by lush greenery and comfortable lounging chairs. After the pool day, you can all load up into a rented golf cart and make the drive to dinner at any one of the award-winning Pine Avenue restaurants. If you’re looking for a relaxing vacation and a taste of what beach living is like, Paradise Point is calling your name.  Note: All Guests Age 18+ must sign an Amenity & Equipment Waiver. Pre-approval of all pets required - Pet Fee per pet, Signed Waiver, and proof of vaccinations required.

Welcome to Waves - Your Perfect Anna Maria Island Getaway! Experience the ultimate beach retreat at Waves, a luxurious 4-bedroom, 3-bathroom vacation home located on the picturesque Anna Maria Island. Nestled just across the street from the sun-kissed sands and azure waters of the beach, this property offers not only breathtaking views of the water but also the convenience of easy beach access just steps away. As you step into Waves, you'll be greeted by the feeling of modern coastal elegance. Recently remodeled from head to toe, this home boasts contemporary design, upscale amenities, and a relaxing ambiance that promises to make your stay unforgettable. The open-concept living area is perfect for spending quality time with family and friends. Sink into plush sofas while enjoying a movie night on the large flat-screen TV, or simply unwind with your loved ones and relish the soft sea breeze flowing in from the nearby Gulf of Mexico. Large windows bathe the room in natural light, and the sight of the water just outside is a constant reminder of the paradise that awaits you. Prepare culinary delights in the fully-equipped gourmet kitchen, complete with top-of-the-line stainless steel appliances, granite countertops, and ample space for the aspiring chefs in your group. The adjoining dining area offers seating for everyone, creating an ideal setting for shared meals and memorable conversations. The bedrooms at Waves are designed to provide the utmost comfort and privacy. The master suite features a king-size bed, an en-suite bathroom with a luxurious walk-in shower, and direct access to a private balcony with panoramic water views. The three additional bedrooms are equally inviting, featuring cozy beds and charming decor that perfectly complement the beach ambiance. Beyond the property, you'll find an array of activities and attractions to explore on Anna Maria Island. From water sports and fishing charters to boutique shopping and art galleries, there's something for everyone in this delightful beach community. Book your stay at Waves today and immerse yourself in the perfect blend of luxury, tranquility, and beachside bliss. Whether you're seeking a family vacation, a romantic getaway, or a fun-filled retreat with friends, Waves promises to be the vacation home where beautiful memories are made. Key Features: 4 bedrooms, 3 bathrooms, bikes, SUP, Kayak included Spectacular views of the water Across the street from the beach with easy access Completely remodeled with modern coastal elegance Open-concept living area with large windows and abundant natural light Fully equipped gourmet kitchen with top-of-the-line appliances Master suite with en-suite bathroom and private balcony Close to a variety of activities and restaurants on Anna Maria Island

**Luxurious Canal-Front Retreat on Anna Maria Island - Your Perfect Short-Term Rental Escape!** Welcome to your dream vacation destination on beautiful Anna Maria Island! Nestled on the serene canals of this picturesque island's north end, our newly renovated 4-bedroom home offers the ideal retreat for your next getaway. Whether you're a boating enthusiast, a lover of water sports, or simply seeking relaxation and luxury, this canal-front oasis has it all. **Property Highlights:** * **Location:** North End of Anna Maria Island * **Bedrooms:** 4 * **Bathrooms:** 3 * **Accommodates:** 8 guests **Bedroom Configuration:** - Master Bedroom: King-sized bed with ensuite bathroom - Bedroom 2: King-sized bed - Bedroom 3: King-sized bed - Bedroom 4: Two twin-sized bunk beds **Key Features:** * **Waterfront Bliss:** This home boasts a prime canal-front location on the north end of the island with room for a boat (about 7/8 feet clearance during normal tides), allowing you to easily explore the Gulf of Mexico at your leisure. Bring your own boat or rent one locally for an unforgettable adventure on the water. * **Newly Renovated:** Experience the epitome of comfort and style in this recently renovated home. High-end finishes, modern amenities, and tasteful decor ensure a luxurious stay. * **Outdoor Paradise:** Relax in the lanai while overlooking the canal, or take a dip in the private pool (pool in the works) for the ultimate in relaxation. Enjoy dining with the provided barbecue, and soak in the warm Florida sun on comfortable loungers. * **Water Sports Galore:** Explore the tranquil canals with the two paddle boards or kayak. Or, take the bicycles out for a scenic ride around the island to discover its charming shops, restaurants, and pristine beaches. * **Gourmet Kitchen:** The fully-equipped kitchen is a chef's dream, featuring updated appliances, granite countertops, and ample space to prepare delicious meals. A spacious dining area is perfect for enjoying family dinners. * **Entertainment:** The living room is equipped with a flat-screen TV for cozy movie nights, and high-speed Wi-Fi keeps you connected throughout your stay. * **Location, Location, Location:** Anna Maria Island is known for its laid-back charm, stunning beaches, and vibrant local culture. You'll be just minutes away from all the island has to offer, including boutique shopping, dining, and water activities. **Your Dream Vacation Awaits!** Escape to this canal-front paradise on Anna Maria Island's north end and make unforgettable memories with your loved ones. Whether you're seeking relaxation, adventure, or a mix of both, this luxurious home has everything you need for the perfect getaway. Book now and experience the best of Florida living!