Featured Anna Maria Rental Homes Perfect For A Fall Beach Vacation

Anna Maria Island is an incredible vacation destination any time of year, but it especially comes alive in the fall time. Luckily, our Anna Maria rental homes are right in the middle of all the action, giving you access to all the best beaches, food, shopping, and events that the fall season brings. Here are a few of our favorite listings available this fall.

Gulf Breeze Condo Unit D

Looking for a last-minute fall vacation before the Holidays and cold weather are upon us?

Imagine waking up to the sound of waves crashing against the coastline and the smell of the crisp, salty morning air. You can enjoy your morning beverage from the comfort of your own private balcony while overlooking the blue Gulf waters. This incredible 2 bedroom, bathroom property offers you all the amenities you could need for your island vacation.

Direct Beach View

Direct Beach View is located across the street from the beaches of Anna Maria Island. This gorgeous 5 bedroom and 4.5 bathroom luxury property have some of the best views of the Gulf because of its premier location on the north end of the island. This fantastic property is complete with a private heated pool and spa along with many other amenities to make your Anna Maria Island as lovely as it can be.

Once Upon A Tide

Once Upon A Tide is a custom-designed home featuring 4 bedrooms and 3.5 bathrooms that exudes sophistication and lavish amenities. The tropical landscape shades the private pool just enough to make it a perfect location to enjoy the day. If you decide to venture away from this fantastic location, you can explore the infamous Bean Point beach which is only about a mile away. Staying at such a premiere location on Anna Maria Island means that the possibilities are endless for your impromptu Thanksgiving getaway.

Casa Muratti

Looking to host a Christmas vacation on Anna Maria Island? Consider an Anna Maria Island vacation rental to have the most sensational Christmas getaway possible. This home has 4 bedroom and 3.5 bathrooms, so it’s large enough for your entire group. Styled with a touch of Mediterranean flair, you can literally walk to the coastline while staying here.

If you get tired of the beach, you can always enjoy your own private heated pool. This Anna Maria Island vacation rental puts you within walking distance of several boutiques, island shops, and several restaurants. Why not ring in the new year on Anna Maria?

Tuna Cottage

This quaint 1-bed, 1-bath rental is perfect for a cozy getaway. Enjoy creature comforts like wireless internet and TV, and take in your incredible view of the water as you drink your morning coffee or your evening wine. You also have access to a deep water dock, front deck, and community BBQ grill.

Blue Oasis

Blue Oasis is a 2-bed, 2-bath home in the heart of Holmes Beach, perfect for a family getaway. The property has been newly upgraded with state-of-the-art fixtures and appliances, and you will love the convenience of the Professional Linen Service Program. You’ll also have access to a private heated pool and tons of beach equipment for your use.

Aqua Bay

This 3-bed, 3-bath home is great for parties of eight. The canal-front rental provides an incredible view, and you will love retreating to the rooftop deck at night and sitting in front of the fire. Indulge in the tropical landscape, full kitchen, and private heated pool, and take your very own beach cart down to the water!

Coastal Serenity

In the city of Anna Maria, Coastal Serenity is a 4-bed, 3.5-bath home perfect for larger parties. You’re just a short walk away from Pine Avenue, where you will find all the best shops and restaurants. At home, enjoy amenities like multiple TVs and game consoles, a private heated pool and spa, and an oversized rooftop deck with breathtaking views of the water.

The Big Yellow House

The Big Yellow House can sleep up to 14 guests with over 3,000 square feet of the best amenities. Enjoy a fully equipped kitchen as well as a kitchenette, laundry facilities on-site, wireless internet, and our Professional Linen Service Program. You also have incredible views of the water from all around.

Beach Side Vista

With 6 bedrooms and 4 bathrooms, this Bradenton Beach home can suit your entire group. Enjoy the perfect dose of privacy in this home, equipped with two kitchens, two living rooms, and two sets of washers and dryers. You’re less than a minute away from the beach and just a short walk to the local shops and restaurants. You even have open-air decks and a private heated pool to enjoy!

Things to Do This Fall at the Beach

Once you’ve secured your Anna Maria Island lodging, you’ll want some fun things to do during the day. Anna Maria has tons of fun fall events, such as Bayfest, an annual arts festival held every October. You’ll also find fun attractions like the Robinson Nature Preserve, the Coquina Boardwalk, and multiple farmers’ markets in the area. You’re also just a short drive or trolley ride away from Sarasota, opening up even more great opportunities for sightseeing and fun. The possibilities are truly endless when you stay on Anna Maria Island!

There’s nothing better than escaping the hustle and bustle of everyday life with a fun vacation to Anna Maria Island. Our team is knowledgeable and ready to help you plan the getaway of your dreams! We hope you’ll join us for all the fun this fall. For more information on spending the fall season in Anna Maria Island and all of our available AMI vacation rentals, contact us today!

Recommended Rentals

1 & 2 Bedroom Vacation Rentals

Beachfront Vacation Rentals

Dog Friendly Vacation Rentals