Top 13 Vrbo Rentals on Anna Maria Island Near the Beach - Trips To Discover (2024)

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Adorable Vintage Anna Maria Cottage

This villa sleeps five people and has two bedrooms and one bathroom for your trip to Anna Maria Island. It is a ground-level rental within walking distance of Gulf beaches. It’s a duplex unit with a shared, heated pool and chaise loungers, as well as a BBQ grill. The Vrbo rental is centrally located on the island and in a walkable area from the free trolley stop and restaurants. You’ll be in a quiet area on the island and love having your own space to soak up the Florida sunshine.

Two-Bedroom, Two-Bathroom, Ground-Level Home with Heated Pool

Here’s a highly rated Vrbo rental that is great for a week-long stay on Anna Maria Island. It sleeps four people and has two bedrooms and two bathrooms. The home offers a full kitchen, dining area, living room, and laundry room. There are TVs in each of the bedrooms and in the living room. You’ll love the heated pool with a large sun shelf, especially if you have young children. The patio at the home also offers a gas grill, lounge chairs, dining tables, and a shed with beach items. You can access the free trolley at the stop at the end of the street.

Blue Pelican

The Blue Pelican is an 850-square-foot house for rent in Holmes Beach and on Anna Maria Island. It is just three blocks from the beach and has two bedrooms and two bathrooms. At this rental home, you’ll have a private, heated pool and outdoor shower. There are also pool loungers, Adirondack chairs, and an outdoor patio dining table with an umbrella. Beach towels and chairs are provided too.

Gulf View Retreat

If you’re looking for a house rental on Anna Maria Island, this Vrbo listing is a popular choice. It is a 1,580-square-foot house that sleeps eight people and has three bedrooms and four bathrooms. You’ll be on the top floor of a two-story home. There’s a new pool with a large sun shelf and sitting shelves at the home. The rental also includes beach supplies, two kayaks, a paddleboard, open decks with Gulf of Mexico views, a big yard, and a fire pit. Inside the home, you’ll find high-speed Wi-Fi, cable TV, and a “crows’ nest” third-floor balcony for enjoying the sunsets and starry night skies. If you have a larger group, you can rent out the first floor of the home separately too and accommodate up to 18 people with six bedrooms and two sleeper sofas in the common areas.

Dog-Friendly, Lovely Pool Home

You’ll be just 250 steps from the beach when you stay at this pool home on Anna Maria Island. It is located at 202 56th Street, #1, in Holmes Beach. The Vrbo property sleeps six people and has three bedrooms and two bathrooms. You’ll have access to a shared saltwater pool, shared BBQ grill, and shared laundry machines here. There are three king-size beds in the home, and the Vrbo host provides guests with beach supplies. This is a dog-friendly rental when you pay an additional fee of $150. There is a two-dog limit per stay.

House with Private Pool, Walk to Beach

With about 1,500 square feet of space, three bedrooms, and three bathrooms, this house is available for rent on Anna Maria Island. The rental is a ground-level duplex with a private, heated pool and beach entry. There’s also a waterfall, swim-up bar, outdoor shower, tiki hut, and tropical landscaping in the outdoor area. From the cottage, you can walk to the free island trolley, shops, restaurants, and the beach. Families love staying here because of all the little extras that make the vacation rental feel like home.

Naut 2 Shabby Bungalow

With about 700 square feet of space, this vacation rental home sleeps four people on Anna Maria Island. The rental has one bedroom and one bathroom. It’s a cute bungalow on the north end of the island and a block from City Pier. The sandy beaches are just four blocks away. This property has the added bonus of a separate three-bedroom, two-bathroom rental at the front of the property that you can also rent for a larger group. The Vrbo host provides guests with beach gear, a grill, and a ping pong table.

Best Little Beach House on Anna Maria Island

Two people will love staying in this 650-square-foot house that has one bedroom and one bathroom on Anna Maria Island. The home has been totally renovated and is a one-minute walk (five houses down) from the white, sandy beaches. This is not a duplex home like many of the rentals on Anna Maria Island are, but rather a private, one-bedroom house with its own private pool. The house is decorated with coastal furnishings and comes with a fully equipped kitchen, beach supplies, and luxury bedding.

Sweet Escape Beach Cottage

Four people can stay at this quaint 1930s beach cottage that is full of personality on Anna Maria Island. The home has two bedrooms and one bathroom, as well as a kitchen and all the basic beach supplies you’ll need for your vacation. With this vacation rental, you’ll have a large yard with trees for shade. There’s also an outdoor fire pit, BBQ grills and off-street parking for two cars. The beach is just a three-minute walk (400 feet away) from the vacation rental home.

Two-Bedroom, Two-Bathroom Duplex, Steps from the Beach

This 800-square-foot house is available to rent on Vrbo to accommodate four people on a trip to Anna Maria Island. The home has two bedrooms and two bathrooms in a half-elevated duplex unit that’s just steps from the beach. The sleeping arrangements are a queen-size bed in the master bedroom and two twin-size beds in the second bedroom. It also offers a brand-new kitchen and comfortable furniture. You’ll be just behind Gulf Boulevard at Bradenton Beach on Anna Maria Island when you book this rental property.

House in Beautiful Bean Point Location

Another Anna Maria Island option is this 900-square-foot cottage rental that sleeps six people. The home has two bedrooms and one bathroom on the ground floor. From here, it’s just 200 feet to the beach. The Vrbo host provides guests with bicycles, which is a perfect way to head out to one of the local restaurants or visit historic Pine Avenue. There are many shops, art galleries, and museums within just a 10-minute bike ride too. The Vrbo hosts are also open to discussing vacation rental trades with other property owners in preferred destinations.

Salty Snapper Beach House

The Salty Snapper Beach House is a 2,200-square-foot rental house that sleeps eight people on Anna Maria Island. It has three bedrooms and three bathrooms, as well as a pool table, wet bar, and 55-inch TV in the upstairs game room. The home is equipped with a modern kitchen, gorgeous dining room, and laundry room. You’ll have a fenced backyard here to relax as you sit in the hammock, play cornhole, and grill some dinner. Another big perk of this rental is the large rooftop deck that offers views of the beach and bay. The beach is just steps away from the Gulf of Mexico. It’s also nice to use the multi-purpose path across the street with a rental bike or on a Segway tour.