Anna Maria Island, on the west coast of Florida, is an island with the Gulf of Mexico and Tampa Bay as its neighbours - an island that attracts many visitors who come for its relaxed vibe, broad beaches with snow-white sand, and crystal blue waters. Once you are here, you can choose to stay in either of its three cosy towns: Bradenton Beach in the south, Anna Maria in the north, or Holmes Beach in between.
If you’re in Anna Maria, you’ll find so many things to do, including browsing at Pine Avenue, the shopping district of this small resort city. Lined with galleries, restaurants, and eateries, it has everything you need. Pop into the Anna Maria Island Historical Society Museum, a restored 1920s cottage, or step onto the nearby City Pier that dates back to 1911. If you stay in Bradenton Beach City, have fun shopping at the Bridge Street Market, which sells food, art, and jewellery. For a leisurely night, go to the dive bars at Holmes Beach and chill out with local surfers. On Anna Maria Island, outdoor sports, like fishing, kayaking, hiking, and bike riding, are all great activities to do! It’s easy to get here - just book a ticket to Sarasota Bradenton International Airport and drive or bike to either of the three towns. Here are a number of vacation rentals available! Not comfortable leaving your pets behind? Check out our list of pet-friendly Vrbo vacation rentals on Anna Maria Island, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Modern condo with a heated pool (from USD 243)
This modern condo has beautiful interiors with a marine vibe. You can bring your pets for a fee of 250 USD and spend quality time with them here. Grab your towel and walk to Bean Point Beach, just 0.6 mi (0.97 km) away. You can participate in fun activities such as boating, kayaking, scuba diving, and jet skiing.
After an exciting day, make coffee and catch up on some television shows or movies on the DVD Player. You can also jump into the heated pool and soothe your body.
Top guest reviews
Cleanliness:
place was updated and cleanoverall clean and well equipped kitchenhouse well stocked and cleanHost:
it was also helpful to have the laundry area as wellRead more reviewsLocation:
we enjoyed the location of the condo as it was very close to the ocean and the downtown area
2. Luxury condo with an amazing view (from USD 250)
Imagine waking up to a beautiful beach view; this luxury condo will make it true with its convenient amenities. You can have fun under the sun all day since Manatee Public Beach is less than a mile away. So get ready for exciting activities such as scuba diving, parasailing, snorkeling, and dolphin watching.
Take your pet to the beach and play catch on the white sand. You can watch your favorite movie on the television or browse on social media using Wi-Fi after a tiring day out. If you’re a home food lover, you can make your favorite dishes in the well-stocked kitchen. There is also a private pool in the building.
Top guest reviews
Amenities & Room:
the pool was first class and view from the patio at sunset was beautifulloved the decor and my son loved having his own bedroom bathroom and tvRead more reviewsLocation:
literally steps to the beach amazing pool and so walkable to many restaurantsgreat location and property in anna maria iskand
3. Gorgeous beachfront cottage with a fully equipped kitchen (from USD 209)
Bask in the beautiful gushing waves on the Gulf of Mexico by staying in this romantic cottage. It’s a gorgeous, old-fashioned cottage surrounded by jasmine and bougainvillea. You can try different recipes in the fully equipped kitchen and eat while watching the television.
This cottage allows up to two cats or dogs with a fee of 100 USD per pet, and they must be less than 20 lbs (9.07 kgs). Watch the sunrise over the ocean from Bradenton Beach while your dog runs along the beach with a ball. Guests can also swim in the heated pool gazing at the massive ocean.
Top guest reviews
Cleanliness:
extremely clean and tidythe unit was clean and i appreciated all of the communication from the ownerRead more reviewsHost:
we utilized the wonderful guide to the island the owner put together
4. Beautiful beachfront cottage (from USD 300)
During your stay here, you can bring your pet with an extra charge of 50 USD; two pets must be less than 50 lbs (22.68 kgs). Put your feet up and gaze at the beautiful beach while eating delicious fish fry made in the fully equipped kitchen. Guests can participate in fun activities such as kayaking, fishing, jet skiing, and more.
Capture the island’s beauty surrounded by the beach and bay and upload them on social media using free WiFi. You can enjoy a peaceful walk on the beach after having dinner.
Top guest reviews
Cleanliness:
nice clean place - great locationsuper clean well updated and great locationwasher/dryer in good clean shape nice towels…Host:
host was very responsiveRead more reviewsLocation:
just a short walk to a beach access great little space
5. Luxurious manor with Gulf views (from USD 2800)
This grand and luxurious manor is perfect for the ultimate beach getaway. It boasts 9 bedrooms and 9 full bathrooms. The areas inside the house as well as the spacious porch provide plenty of room for up to 22 guests and their pets. It also provides modern amenities, including a cable TV, pool table, video games, and Wi-Fi. The best part of this rental, however, is the private heated pool with a waterfall.
Located on the waterfront, this rental rewards guests with panoramic views of the Gulf from its rooftop deck. Guests can also enjoy views of the sunsets or occasional glimpses of dolphins swimming in the distance. The property also has its own 2 elevators. Nearby places include the Fish Hole Adventure Golf and Historic Bridge Street Pier, both just 0.7 mi (1.1 km) away.
Top guest reviews
Amenities & Room:
and a bathroom on ground floor would be niceluckily she was not injured and the table was not damagedan updated picture showing the pool table would be helpfulCleanliness:
the home was clean when we arrivedthe house is fantastic well appointed spacious and cleanit was clean and move-in ready when we got there on the first daypools were great clean and in use throughout the day and eveninghouse is massive so requires a huge undertaking to keep clean beach stunning a lot of stairsHost:
management was helpful and responsive but not after 430pmeven the maintenance and cleaning staff (we met on their way out) were very friendly and helpfulRead more reviewsLocation:
perfect location had a fabulous timeit is a perfect place in a perfect locationthe location was equally fantastic right on a very beautiful gulf beach with perfect sand and waterthe house was beautiful and comfortable and close to the waterotherwise a great week shops restaurants and bars are all within walking distance
6. Well-furnished retreat with a private pool (from USD 1325)
Named the Beachbreeze, this luxury home is located just within walking distance of the beach. It offers 6 bedrooms and 5 bathrooms, ideal for a group of up to 12 guests plus pets. Aside from the usual amenities, this property has a game room with a pool table, a ping-pong table, a foosball, and some video games that are perfect for all-around fun. There is a private pool as well.
Outside, the fenced yard provides a great playing ground for pets. The rooftop deck and balconies also deliver stunning island views. In addition to Manatee Public Beach just 0.3 mi (0.5 km) away, other notable places nearby also include Anna Maria Museum and National Park and Historic Green Village which are both just 2.2 mi (3.5 km) away.
Top guest reviews
Amenities & Room:
nice heated pool and hot tubgreat pool hot tub and outdoor bar/grillhouse was fantastic pool area had been a bit overlooked when we arrivedthis is a very comfortable house with 6 good size bedrooms and lots of bathroomsHost:
the owner stopped by both upon check in and check out he is very friendly and sociableRead more reviewsLocation:
the location is ideal easy walk to beach quiet street near restaurants and island shuttle busthe location is simply perfectthe house and location were perfectnice easy walk to the beachalso the house is within walking distance of several delicious bars and restaurants
7. Waterfront home with a private boat dock (from USD 336)
This waterfront home is just as lovely as its name, Anna Maria. It is fully furnished and spacious enough to accommodate up to six guests. For a fee, pets are also welcome to stay. Anna Maria offers three bedrooms and two full baths. Guests can enjoy access to the well-equipped kitchen, dining area, garage, and screened-in pool. Amenities also include a Wi-Fi connection, a TV, and a ping-pong table for entertainment.
There is a private boat dock as well, perfect for anglers who are looking for a great catch. This property is also close to Bayfront Park, Rod and Reel Pier, and Pine Avenue. Other notable places nearby are Bean Point Beach, Anna Maria City Pier, Anna Maria Island Museum and National Park, and Historic Green Village, which are all just 0.3 mi (0.5 km) away.
Top guest reviews
Read more reviewsCleanliness:
clean well kept fun family friendlythe house was spacious with nice rooms and very clean
8. Spacious retreat with a heated pool and spa (from USD 736)
Beautiful and luxurious, this rental provides plenty of room to accommodate up to 12 guests. It offers 5 bedrooms and 4 full bathrooms. Spaces like the well-equipped kitchen, dining area, and balcony are accessible to guests. For a fee, small dogs can be accepted in this rental. Other amenities include a Wi-Fi connection, a TV, and a game room complete with a pool table, foosball, and video games. There is a private pool and spa on the property as well.
The fenced yard outside provides a secure area where your pets can play around. The rooftop deck also features stunning views of the island and the gulf. Guests can visit Bean Point Beach, Island Players, and Palmetto Avenue Beach, which are all just 0.1 mi (0.2 km) away.
Top guest reviews
Amenities & Room:
backyard pool and hot tub was a great a great place to chill after beachCleanliness:
the house itself was very clean and spaciousHost:
family friendly house with an updated feel and room to spread outRead more reviewsLocation:
the location was absolutely perfectwe enjoyed the locationthis house was at a great location
9. Mediterranean-style cottage with a pool and tiki table (from USD 359)
Featuring Mediterranean-inspired interiors, Calypso Cottage provides an ideal accommodation for up to six guests. It offers three bedrooms and three full bathrooms. For a fee, small dogs are also welcome to stay in this rental. There is a game room that is complete with a ping-pong table and video games. Guests are free to use the private pool as well as the spa with a swim-up tiki table.
The property also has a fenced yard where pets can play around. It is located on a low-traffic street near shopping spots and restaurants. Guests can also head down to Manatee Public Beach, Anna Maria Sound, and Bradenton Beach Marina, which are just 0.1 (0.2 km), 0.2 mi (0.3 km), and 2.2 mi (3.5 km) away, respectively.
Top guest reviews
Amenities & Room:
a lot of amenities and the beds were very comfortableCleanliness:
house was very clean and niceand it was also very clean which was important to usthe location was great and the house itself was very clean and wonderful to stay atthe home was beautiful and clean and had the basics of everything we neededHost:
the staff was great and helped us along the wayRead more reviewsLocation:
the location was pretty goodgreat walking location to beach and storeseasy walk to the beachwe couldn't have found a more perfect location for our stay
10. Ground-level duplex with beach access (from USD 378)
This ground-level duplex is ideal for up to six guests and two pets. It offers three bedrooms and three full bathrooms. Beach chairs, essentials, and a wagon are provided for guests. Should guests want kayaks to water sports gear, there are multiple rental companies available nearby.
In addition to a two-car driveway and a fenced yard, this rental also boasts a large heated pool with beach entry. There is a waterfall and swim-up Tiki hut as well. The beach is just 0.3 mi (0.5 km) away. There are also plenty of restaurants and shopping nearby.
Top guest reviews
Amenities & Room:
the ac pumped really cold air the couches were comfy and the pool and pool area were amazingnice to have the heated poolthe furnishings are beautiful and the kitchen has everything you can possibly needperfect set up with comfortable beds and furnishings pool right out the back doorthe kitchen cabinets are very well stocked with anything you would need pots and pans bowls small appliancesCleanliness:
very clean and updated decorthe property was very clean and well stocked with everything you needthe beach decor was high end clean and just as advertisedeverything was sparklingly clean and the bedrooms and bathrooms were beautifulhouse was clean and had everything you would need for a comfortable vacationHost:
property management responsive and friendlyowners management always friendly and promptly helpfulthe owners ensured we were well prepared & checked on usowners allowing our dog was a must for us and we appreciate thatRead more reviewsLocation:
great location on the island to restaurants and shoppingi loved the location as it was near everything and really close to the beachlocation is great with several restaurants within walking distance and plenty others just a short ride awaylove the location and the housecute house great location minutes to walk to the beach
11. Charming cottage with private pool (from USD 229)
This is described as a dream vacation cottage. Indeed, this charming cottage is decorated in different shades of blue and has cream-coloured furniture, in line with the beach theme. Your dog is welcome at this rental for a small fee. The cottage is only 200 steps from the beach. Outside, there is a pool with lounge chairs, perfect for watching the sunset, under the swaying palms.
A beautiful vacation home with Wi-Fi, cable TV, and a washer and dryer, you’ll definitely feel like you’re in a dream vacation house here. Hop on the free Island Trolley to shop on Pine Avenue, where you’ll find the best boutique, vintage, and local shops on Anna Maria.
Top guest reviews
Amenities & Room:
personally is one bedroom had 2 twin beds rather than a queen bed But for families with children the twin beds would be idealvery well equipped private close to the beachThe only down side for our stayLoved the privacy and short walk to the beach Nice private poolIt was fine until I got out:)Cleanliness:
Up to date and very cleanHost:
the road was not heavily traveled homeAnd the back outdoor area with the pool was wonderfulespecially the close proximity to the beachso glad we could bring our dog tooWe loved everything about our stayRead more reviewsLocation:
There are several restaurants nearby and ice creams shopsThe location is near to the beach and in a quiet areasteps to the beach quiet north end neighborhoodThe house was located in the perfect spot for us right near the ocean and not a busy streetWe liked Anna Maria and the house
12. Poolside apartment with views of the gulf (from USD 200)
This one-bedroom retreat has a fenced backyard, perfect for your dog to roam around. There is also a heated pool, with lounge chairs and patio tables around the pool. The air-conditioned house has all-new cabinets, flooring, shower, and finishes. Amenities include heating, a washer and dryer, Wi-Fi, and cable TV.
There are four units for rental here. From the apartment, you can watch sunsets and sunrise from your front yard. Or, walk just a few minutes to the sandy white beaches and the shops and restaurants. There is a gas grill and barbecue area for outdoor cooking.
Book your dream vacation on Anna Maria Island, Florida
If sunny beaches and windy sea breezes tick your getaway boxes, then pack your suitcase. If you are not able to keep your furry buddies at home, bring them along. Book your dream vacation in one of our adorable apartments or even a luxury Airbnb.
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