There are lots of well-known vacation destinations in the Sunshine State, and then there’s Anna Maria Island. This is one of Florida’s best-kept secrets and a barrier island on the Gulf Coast that’s definitely worth checking out. When you plan your trip to this charming area, you can check out shops and galleries, enjoy local eateries and bars, and spend time on the lovely beaches. Then at the end of the day, stay at one of these fun Airbnb rentals to really settle into the island life and totally relax!
Dog-Friendly Oasis with Heated Pool
Vacationers with dogs love this house that is ideal for up to eight human guests. It has a pool, stocked kitchen, tropical landscaping, and is on the quiet northern end of the island. You can walk or bike from here to historic Pine Avenue. From this rental property, it’s a two-minute walk to the Seagrape Beach access and a six-minute walk to Cypress Avenue Beach access. Other amenities here are a 42-inch flat-screen TV, sleeper sofa, and built-in closet system.
Old Florida-Style Cottage with Private Pool
Dogs are welcome to join you at this Airbnb rental that has a private heated pool and is within walking distance from the beach. Known as the “Mangrove Cottage,” it is one house away from the Gulf of Mexico sand, so start your mornings with a walk on the beach. The home has an open floor plan, free Wi-Fi, laundry machines, and coastal colors for the décor. It is a pet-friendly space that also offers parking spaces for three cars in the car port and easy access to the free trolley. Up to six people can stay in this cottage with its two bedrooms and two baths in Anna Maria.
Turtle Cottage
One of the hottest Airbnbs in Anna Maria is this cottage that sleeps up to four people. It has one bedroom and one bath, and it’s on the quiet north end of the island. You’ll be just two short blocks from the beach here. The sunrises and sunsets can’t be beat when you stay in this 800-square-foot, open-floor-plan cottage. It has a private patio area with a washer and dryer, a heated pool and spa, and a private outdoor shower. The outdoor dining area is nice and has an electric grill and umbrellas. The sleeping arrangements here are a king-size bed in the bedroom and a sofa bed in the common space. Other amenity perks include Wi-Fi, free parking and a TV.
Canal-Front Cottage with Pool & Hot Tub
You’ll love this vacation rental cottage that’s close to the beach and accommodates six guests with two bedrooms and two en-suite bathrooms. There’s a private pool and hot tub to use here. You’ll enjoy the classic Florida architecture, modern décor, and tropical landscaping at this rental. The space also comes with a backyard for outdoor dining, a fully equipped kitchen, free Wi-Fi, and other convenient amenities.
Blue Heron Cottage
This is an adorable cottage in Anna Maria and one that works well for up to four people. It has one bedroom and 1.5 baths on the quiet north end of the island. It’s two short blocks from the beach and near the Fern Street/Alamanda Road intersection. The space is about 800 square feet in size and has an open floor plan. Your host here provides an electric grill, wagon, beach chairs, and umbrella. Other perks are Wi-Fi, TV, laundry, and free parking. You’ll love the sunsets at Bean Point Beach while staying here!
Steps to the Glorious Gulf
Rent this house on Airbnb for up to six people and you’ll have two bedrooms and two baths all to yourselves. It’s on a quiet street in north Holmes Beach and a three-story house that’s perfect for a beach vacation. Guests enjoy the well-stocked kitchen, TVs, Gulf views, beach chairs and towels, and a large master bedroom. Beach access is just two houses away from here, and you also won’t be far from restaurants, bars, and the supermarket.
Adorable One-Bedroom Condo with Shared Pool
For a great apartment option in Anna Maria, consider this one for up to four people. It has one bedroom and one bath, as well as a shared heated pool, patio area, and outdoor seating with BBQ grills. The laundry room is also shared. The kitchen is fully stocked here, and there’s a pull-out sofa to sleep two people. Guests who book this Airbnb enjoy the private patio area and being in a quaint space on the first floor. Dogs are allowed here with some weight and breed restrictions and for an additional pet fee.
Canal-Front Home with Heated Pool, Dock & Lanai
Here’s an Anna Maria vacation home that accommodates up to eight guests and that has a beautiful pool and hot tub. Guests stay in the three bedrooms and use the two baths here while also enjoying a private canal-front dock. The home is just two blocks from the beach, and the pool is heated. It’s on the quiet north end of Anna Maria Island and has abundant parking. It welcomes guests with a boat dock, Wi-Fi, and plenty of tropical charm.
2-Bedroom Beach Home
Here’s an updated family home that’s within two blocks to either side of the island. It’s near a small park and half a block from restaurants. You’ll love the location of this two-bedroom, two-bathroom house for up to six people and the enhanced cleaning and sanitation protocols practiced by the hosts. This home has two queen-size beds and a couch for sleeping. It also offers a laundry machine, a hot tub, Wi-Fi, a kitchen, a dedicated workspace, and free parking. Stay here to be in a safe and quiet neighborhood that’s two blocks from the beach.
