The 5 Best Anna Maria Island Beachfront House Rentals

Last updated: 10/3/2022 Anna Maria Island is a hidden gem barrier island that is located off the coast of Bradenton, Florida. The island is at the South end of Tampa Bay, the opposite side of Tampa/Clearwater. That’s pretty fitting, because the “vibe” here is opposite of those areas as well. On Anna Maria Island, bikes and golf carts are the most common form of transportation; in Clearwater it’s cars and traffic jams. Anna Maria Island isn’t home to any high rise hotels or condo’s (trading those for secluded beach cottages and homes), a stark contrast to the the towns on the other side of the bay. There are some fantastic beachfront Anna Maria Island house rentals available on VRBO, and hopefully this list gives you some ideas of what to look for.

5. 3BR Beachfront Anna Maria House Rental with a Private Beach

This 3BR Anna Maria beach house rental is located on the quiet North side of the island. If you are looking for a rental that is close to the water, this is about as close as it gets. If you step off the back deck, your toes hit the sand. Take another 20 steps and they are in the water. The second level deck goes end to end across the entire house, and is a great place to take in a sunrise over the blue waters of the Gulf.

We love the location of this home. The famous Waterfront Restaurant ( a 5 minute walk down the beach, with amazing food and drinks on the water. Whether you want to travel around the island by bike, golf cart or car, this central location makes everything about 5 minutes away. With 5 bedrooms and a pullout couch, this rental is rated to sleep 8 guests. Another perk of this house is it is one of the rare pet friendly Anna Maria Island rentals. If we are nitpicking for a downside to this rental it would be that if you do have 8 guests, the 2 bathrooms can feel a little cramped at times.

Average VRBO Review Score: 4.8/5.0 (100+ reviews) Check Availability and Rates: 3BR Anna Maria Beachfront Rental House-VRBO Listing

4. Luxury 4BR Anna Maria Beach Villa with Private Pool

This 4BR Anna Maria Island beach villa is located just a few blocks down Bay Boulevard from the first house on this list. This is a really high end property at a great price per bedroom. If you take the beautiful heated pool into consideration, it’s an even better value. That isn’t too say this house isn’t expensive, it most definitely is, but 4 rooms at a beachfront 5 star hotel would almost always be significantly more expensive. This villa is beautifully decorated with modern styling.

The private beach access off the pool gives you an expansive stretch of white sand beach. The calm waters off the beach are perfect for taking kayaks out or just going for a swim. This Anna Maria Villa is rated to sleep 8 comfortably, with enough living room space for everyone to stretch out at the end of a long beach day. The kitchen is equipped with high end appliances with plenty of seating for cooking for a group. This is a great option for those looking for a high end 4 bedroom Anna Maria beachfront villa.

Average VRBO Review Score: 4.9/5.0 (30+ reviews) Check Availability and Rates: 4BR Luxury Anna Maria Beachfront Villa Rental-VRBO Listing

3. 2BR Anna Maria Island Beachfront Cottage on Holmes Beach

Anna Maria Island Cottage Rental

This beachfront cottage is located at the southern end of Anna Maria Island on Holmes Beach. This cottage is definitely smaller than the two rentals so far on this list, but it is also the first with perfect reviews. The “old Florida” feel of this cottage makes it a perfect choice for a family or even just a couple. The hammock overlooking the beach is a perfect place to relax. The tall palm trees in the backyard offer natural shade to cool off.

Anna Maria Island Beachfront Cottage

The location of this cottage is fantastic. The Anna Maria Island Cafe and Beach Bar ( is right down the street. They offer live music and great food and drink directly on the beach. There are many other great restaurants in this area as well. This cottage isn’t over the top fancy, but cozy beachfront cottages like this are a part of Florida that is quickly disappearing. High rises have taken over, but there are still a few hidden gems like this out there if you look hard enough.

Average VRBO Review Score: 5.0/5.0 (40+ reviews) Check Availability and Rates: 2BR Anna Maria Beachfront Cottage Rental-VRBO Listing

2. Nest on the Beach, a 5BR Anna Maria Island Beach House

Anna Maria Beach Rental

Nest on the Beach is a 5 bedroom all suite Anna Maria Island beach house. This house is located on the far North tip of Anna Maria Island. This spot on the tip of the island gives you panoramic views of the ocean from any of the 3 levels of the house. The ground level has a beautiful heated pool and giant hot tub. Part of the pool is covered by the 2nd floor covered patio. This is really nice because you can choose between cooling off in the shade or soaking up the sun without even getting out of the pool. The outdoor shower off the pool and beach access even has a rainfall shower to rinse off the sand.

Anna Maria Island Home

The 5 bedrooms are all suites overlooking the beach, with attached bathrooms. This is an ideal layout for an adults trip. No more drawing straws for who gets the master bedroom! It was a really hard choice between Nest on the Beach and the house that took our top spot. The VRBO reviews for this property are spotless, with many return guests. You absolutely cannot go wrong with this house or the next if your group requires one of the biggest Anna Maria houses on the beach.

Average VRBO Review Score: 5.0/5.0 (60+ reviews) Check Availability and Rates: 5BR All Suite Anna Maria Beach House Rental-VRBO Listing

1. Halcyon House, The Highest Rated Anna Maria Island Beach House Rental Available

Anna Maria Island Beachfront Rental

This 4 bedroom, 4 bathroom beach house is one of the highest rated properties we’ve ever seen, not just in Florida, but the entire United States. With over 150 verified reviews, the average VRBO review score is a nearly impossible 5.0/5.0. That is an absolutely incredible feat, and one that the owner, Kelly, takes great pride in. She makes sure every guest has a fantastic experience, and it shows. This home was even featured in Coastal Living Magazine. This is one of the best overall Anna Maria Island beachfront house rentals available.

Anna Maria Island Beach House

With incredible views of the beach from pretty much every room in the house, you will have a hard time picking which one to relax in after a day on the beach. This house is located directly on Bean Point, on the North end of Anna Maria Island. You owe it to yourself to view the VRBO listing for this property to see more pictures of this incredible beach house.

Average VRBO Review Score: 5.0/5.0 (150+ reviews) Check Availability and Rates: 4BR Halycon House, Anna Maria Island-VRBO Listing

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