Cottage holiday rentals in Anna Maria

Very responsive, helpful hosts and a wonderful location with lots to offer.

We absolutely loved it here. It was very clean and had everything we needed. Hot tub was a great amenity. The shed full of beach needs was amazing! Definitely would stay here again!

Cozy, comfortable, yet two stories with plenty space to stretch out, scenic view with a hot tub, nice balcony view for coffee in the morning. Can’t go wrong.

This is our third stay on AMI at this exact property, and - I don’t know how Craig does it - but every trip to Kiwi Cottage gets even better! The house, pool and grounds are beautiful. We are a family of 4 and brought two friends of our daughters’ this year, and even with more people, the house and pool felt spacious and comfortable. The girls and their friends absolutely loved the location, and paired ice cream with beach sunsets every night this past week. We also rented their golf cart, which was super convenient for dinners (Harry’s on Father’s Day was a favorite) and exploring the island (especially bc it fits 6 people)! Always an amazing week on AMI at Kiwi Cottage! We’re already talking about next time. Craig is a great host and extremely friendly and responsive! He’s always available for questions and recommendations - we feel so lucky that we found this listing years ago, and can’t wait to come back again.

Anna was extremely helpful and accommodating for our last-minute trip with the kids. Her place was super cute and very clean and well kept and we would be happy to recommend it to friends and family or return ourselves. Thank you so much, Anna!

The house was cute, cozy and beautifully decorated. Laura was very responsive when communicating. Our family of 4 stayed for 3 nights and enjoyed the outdoor space and game room a lot. Plenty to do and lacked nothing. Just be warned about the mosquitoes if you plan on spending long periods of time in back patio area. Bug repellent was provided, however we were still eaten alive. This however did not ruin our overall experience. I would totally recommend this location to anyone and would definitely like to visit again.

My boyfriend and I had a wonderful 5 night stay at Amy's for my first visit to Florida. The space was clean, the bed was comfortable, the kitchen was well stocked and the outside space was a peaceful area to spend our mornings. The hot tub in the evening was a perfect way to end the day of exploring. Short driving distance to the beach and other lovely neighbourhoods. We would absolutely recommend, and would be happy to stay again.

Small but cozy place. Perfect location to walk to the beach or to get something to eat.

Really cute place! And close to everything in downtown Gulfport Florida. Great small flooring community with a great community vibe!

We LOVED staying at Christopher’s. The apartment was exactly what we needed. The neighborhood is adorable and so close to downtown. Christopher was an absolute gem of a host who went above and beyond to make sure we had a great stay. So grateful! Would return.

Had a great stay ! Fishing was fun and right across the street Would stay again for sure !

We absolutely love staying at this property! It is our third time booking. The cottage is always impeccably clean and in a very safe area. It is stocked with everything you need. We love Coral Cottage! And Barbara is very friendly and so responsive. Dunedin is an amazing, quaint little town with so many wonderful food choices. Cafe' Alfresco is our personal favorite. Barbara's cottage is just a couple blocks from downtown Dunedin and only a 15 minute drive to Honeymoon Island State Park or Clearwater beach. I always pick up a piece of jewelry as a memento when we go on a trip. Just kitty-corner from the Airbnb is a charming jewelry store filled with beautiful, unique pieces that are reasonably priced. Romantique Jewelers. Just ask for Kimber, she's a doll! Don't hesitate to book this property for your next trip!!!

Cozy place perfect for a family. Neighborhood was quiet. The beach was a flat 5ish minute walk away.

Very nice place. Close to all the major attractions in the area. My family enjoyed the stay!

You can truly tell that these owners put their all in to what they do. The suite was so clean and nicely decorated and they went the extra mile to include everything you might need. They even included a sweet treat at check in which we enjoyed. We will definitely be back again!

Beautiful little house, only a 1 block walk to the beach. Many restaurants, bars, shopping areas all within walking distance. The sound of the pickle ball players and laughter in the park while sitting on the back patio was a very nice touch! Overall fantastic experience, we will be back!!

Host was responsive, friendly, and willing to allow our family to stay and check-in rather late in the evening when we had to vacate our prior arrangements unexpectedly. Her place was clean, matched description and photos, and exceeded expectations.

Everything about our stay was as near to perfection as possible.The cottage interior is decorated in a modern minimalistic way to make the small cottage feel more spacious. Everything was clean, and we thought Lisa had thought of everything detail. She quickly responded to our two questions. When I need a place in St. Pete again, hers will be the first choice. Yhanks for making it a very relaxing place to be.

We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️

Location was perfect the beach was a block away, John’s Pass was just 5 minutes away aswell as the opposite way multiple shops about 10 minutes away. Lynne had nearly everything provided what you’d need for a beach getaway. Ice chest, sunscreen, chairs, snacks, umbrella, paddle ball game and more. There was even some cooking condiments in the fridge already aswell as chips. Only one thing we were suprised with is sharing the backyard area along with the host. Other than that it was a phenomenal stay and our host was very attentive.

Cute place for a get away. Communication was top notch. Sent many recommendations prior to trip which helped to plan our stay. Highly recommend this place!

This was our second year of spending a month at Aileen's place. Again, it was so perfect for my husband and I. We did have guests stay for a couple of nights and the air mattress is REALLY nice! Everything about the space is so wonderful. Clean, cute, everything you would need for a month. It is also close to so many beaches (Fort Desoto Park ( our favorite), St. Pete's beach, and Anna Maria Island beaches. It's close to all that Bradenton, St. Petersburg and Sarasota have to offer. We felt right at home the day we arrived and it was hard to say good-bye. We definitely hope to visit again!

This was our second summer in a row staying at the cottages. We always have a blast.

Enjoyed a nice get away for two at a great location that offered relaxed and warming vibes. thank you!