Top Anna Maria Island Luxury Vacation Rentals You Need to Visit

If you’re ready to treat yourself to the relaxing vacation you know you deserve, you’re going to want to spend time in one of our Anna Maria Island luxury vacation rentals! Whether you’re planning a fun trip with your friends or are coming to AMI to celebrate an occasion like a wedding, birthday, or reunion, you want to enjoy your time here in style.

That’s why we’ve got all kinds of luxurious rentals filled with top-of-the-line amenities, all within walking distance of some of the island’s best attractions. Here are a few of our most popular Anna Maria Island vacation rentals to consider! 

The Bayfront

Enjoy your own little slice of paradise right on the bay. This 6-bedroom, 4-bathroom home is suitable for up to 15 guests and provides the perfect setting for creating lifelong memories. Relax in your private bayside pool, or spend time in the fresh salty breeze on your own private dock. We think this rental would be the perfect place for an extended family gathering, as there’s something for everyone to do and there’s so much space! Kids will enjoy Wii and X-box stations on 60” flatscreen TVs while adults can mix and mingle in the two gourmet kitchens, screened-in deck, and spacious living spaces on each floor. At the end of the day, enjoy meals together around an oversized dining table while watching dolphins play in the bay. It doesn’t get much better than this..

The Beach Front

Pass through the entrance of this elegant beachfront home to find unsurpassed luxury and serenity. This three-bedroom, two-bathroom direct Gulf front vacation property is one of a select group of just five beachfront condos, close to Bradenton Beach. Walkout onto your own beachfront balcony to watch the dolphins playing in the morning or to witness the most spectacular sunsets over the Gulf of Mexico. Then step down onto the powdery sands of Anna Maria Island to confirm that you are in paradise.

Mandalay Bay

Large groups are sure to enjoy Mandalay Bay. This property has enough room for up to 20 guests between its 7 bedrooms and 5.5 bathrooms! Inside this stunning 6,500-square-foot home, you’ll have everything you need for an unforgettable stay. Get competitive with your XBOX gaming system or foosball table, cook up a meal in one of your two (yes, two!) gourmet kitchens, or relax in front of one of the numerous flat-screen TVs. You can then step outside to enjoy your rooftop deck with panoramic views of Anna Maria Island, set sail from your private boat dock, or take a soak in your private heated pool! 

The Blue Crab

Don’t need something quite that big? The Blue Crab is perfect for smaller groups of 8 people or less, boasting 4 bedrooms and 4.5 baths. This property is located in the heart of Holmes Beach, right in the middle of the island, which is ideal for those who want to take advantage of all AMI’s best attractions! Your home includes all kinds of luxurious features like an in-home washer and dryer, professional landscaping outside, a private heated pool and spa, and an indoor-to-outdoor swim-up bar! This home was just constructed in 2018 and was custom-built, so you know you’re in for a once-in-a-lifetime experience! 

Blue Water View

Blue Water View is one of our most popular mid-size properties, perfect for groups of 12 people with its 6 bedrooms and 5 bathrooms. You definitely can’t miss this home, thanks to its vibrant, teal-colored exterior! Once you step inside, you’ll see all kinds of amazing features like the open concept living space and stainless-steel appliances, and granite countertops in the kitchen. Outside, you’ll enjoy incredible amenities like your very own heated pool and spa with a swim-up tiki hut, tons of tropical landscaping, a gas BBQ grill, and a poolside lanai with a bar, TV, and pool stereo! 

Anna Maria Grand Beach House

Got a huge group? You can keep everyone all in one place at the Anna Maria Grand Beach House, which offers 9 bedrooms and 9 bathrooms to accommodate a whopping 22 people! It’s hard to find a property that’s more luxurious than this. This brand-new home contains wireless Internet, more than a dozen flat-screen TVs, an XBOX gaming system, a fully equipped kitchen, and even two elevators! When you step outside, there’s even more to enjoy, including a breathtaking view from your rooftop deck! You’ll also find your very own private heated pool with a waterfall, spa, and swim-up bar. 

The Blue Horizon

Another of our largest properties is The Blue Horizon, which has 9 bedrooms and 7.5 bathrooms to suit an incredible 21 guests! This property accommodates so many people because there are 6 bedrooms in the main house and an additional 3 bedrooms in the guest house, perfect for big families who want a bit of privacy. Everyone in your group can enjoy features like the beautiful beachfront location, a private heated pool and a hot tub that fits up to 10 people, and lush tropical landscaping that truly transports you. It’s hard to find somewhere better to enjoy with your friends and family! 

Summer Paradise

Even though this property is named Summer Paradise, guests enjoy this 6-bed, 6.5-bath home no matter the season! Groups of up to 12 people will feel right at home here since this 4,500-square-foot home is easily one of our most exquisite properties. Inside, you can enjoy an expansive kitchen and dining room, luxurious bedrooms and bathrooms, and even a theater area! Outside, you’ve got a lagoon-style pool with a waterfall, water slide, hot tub, and cold plunge. Dine in the covered lanai living area, get a panoramic view from the rooftop deck or walk just two doors down to the beach.