Cottage holiday rentals in Treasure Island

I’ve found my new favorite staycation spot and where I will enthusiastically recommend to friends and family visiting the area. The space was thoughtfully designed, clean, and comfortable. I will miss my morning coffee on the patio amongst all the plants and birds, my daily work sessions in the small quiet office, and the evening dips in the hot tub. Thanks for your thoughtfulness in creating this space!

Our cottage wasn’t ready when we arrived but Captain Al was very responsive and accommodating! He provided us another cottage in a timely manner and generously took care of our dinner tab while we waited. It was very chilly in Florida during our stay and Captain Al brought us an additional space heater to use during our stay. The location is amazing and the cottages are very unique! We’d definitely come back!

Beautiful home, nice & spacious kitchen, and all beach amenities provided. Our family really enjoy our stay, perfect location with really short walk to the beach. Paula was a great host and quick to response. Thank you for our wonderful stay and we will be back.

The cottage was perfectly located in Safety Harbor, close to everything and had all the amenities to enjoy every experience the area has to offer.

First time staying at Capt Al’s cottages and we had a fantastic time! We had everything we needed, easy walking distance to beach, restaurants, and waterfront. The cottage was clean and well supplied, the common area tiki bar vibe was fantastic! We appreciated the use of all the beach chairs, sand toys, ect. Perfect for a family beach vacation!

Great stay for our family! The home is very clean and decorated with a beachy, fun vibe! Great bathroom, comfy beds and lots of places to hang out! The dryer was very helpful with wet towels and beach gear was great. Our favorite part of the home was the backyard. The plunge pool was so fun and we loved the game room and golf. Private yard and we enjoyed the birds over coffee each morning! Recommend for any family!

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!

Ame is a wonderful host! This is the cutest little house, stocked with everything you might need for a stay in sunny Florida! Clean as a whistle, too. Location was perfect, groceries, the beach, pizza and shopping all close by.

Place and location were great! And host was super communicative. It is small but that is expected based on the listing information. Would definitely go back!

Excellent place to stay - had everything promised and was perfect for 3 people. Loved the backyard

Michael’s Citrus Cottage was perfect for our 6 day stay in Dunedin! It had all the amenities we needed. The bed was extremely comfortable, and the shower was one of the best I have seen in all the Airbnbs I have been to. The location is perfect also. Less than a 10 min walk to many restaurants, to 7 microbreweries, and many stores to satisfy your shopping itch. I would stay at Michel’s place again should we travel to Dunedin again.

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.

The house was very nice, not huge, but very accurate with what the pictures showed, and it was actually a lot brighter inside than I expected based on the pictures. Everything was clean and with 5 people, there was plenty of space. They provided beach chairs and an umbrella which was wonderful. We also used the grill which we enjoyed having access to. The only thing we would recommend is more pots/pans/serving bowls, etc. for use in the kitchen - that was a little lacking. Otherwise, communication with the host was outstanding. We had a couple of minor issues that were resolved immediately. They let us check in early and stay late based on our schedule and the fact that no one was coming in behind us. Finally, the location is awesome - right across the street from the beach with easy beach access. We had a great time and would definitely recommend this house.

The cottage was immaculately clean and comfortable. It was stocked with everything you would need such as kitchen necessities, toiletries, extra towels and beach items. The pool was beautiful and even lit up at night. It is a three minute walk to the beach and some of the bars and restaurants. It is a very quiet neighborhood. The host was extremely nice and responsive with everything. We would stay there again. And I loved the free library out front. I left a book in there ☺️If you are thinking about renting this cottage, you definitely should, you won't be disappointed.

This is probably our favorite Airbnb to date! The location is fantastic, on a street full of restaurants and bars, about a block from the beach. Yet, it was quiet! The place is very comfortable, with awesome and quirky decor, two bedrooms, and an air-conditioned, screened-in front porch, which was our dog’s favorite part! Great value!

We really enjoyed our stay at the Indian Shores Beach Cottage! Property was exactly as the photos describe, easy check-in, cute minimal decor which is always helpful traveling with children (less to babyproof), host was friendly and responsive, and best of all.. Location is just one block walk to the beach! A quiet, relaxing, tropical stay for our annual FL getaway! :)

This was my second time staying at The Cottage and when I walked in it felt like coming home again. Everything about the place is pretty much perfect, there is nothing more I could have asked for.

We had to get another rental after our first fell through and Petie was so helpful in getting us set up quickly. Her hosting was attentive the entire time. And the place was so clean, well located and apportioned. The back patio was a great place to have breakfast and watch the boats and birds. It was a good space but ultimately the attentive hosting and being good with a last minute booking were what really pushed this over the top.

Very responsive, went above and beyond!

I recently stayed at this house and had a wonderful experience. It was incredibly clean, with everything spotless and well-maintained. The space had a warm, homey feel that made it easy to relax and feel comfortable right away. It’s clear the hosts put care into making it welcoming. I’d definitely stay here again!

This was the first time staying in an Airbnb and I highly recommend this property and the management company, 5 stars ⭐️ . The home was just as advertised but better. Home was sparkling clean and I own a cleaning business in Tampa, so that says a lot! It was walkable to the beach, great restaurants and grocery stores. Everything you need for the first day/night to get you started on your getaway. The pool was clean and we loved the beach sand area of the pool area! The host and his associates were very responsive. We look forward to staying at this house or any of the other 29 properties the host has!

This super cute cottage is very clean with up-to-date appliances and beautifully decorated with well-thought-out use of space! We stayed for 10 weeks and slept soundly every night due to the comfortable mattress, peaceful & quiet safe neighborhood. The newer fixtures and large washer/dryer were so convenient. Communication with Mary Jane was fantastic. She’s very responsive to questions and even though she lives next door, never intrusive. She’s so gracious we’d be back in a heartbeat! 💗 Truly one of the best experiences we’ve had in the nearly decade of staying in Airbnbs. Location is a bonus as is very walkable to Bay/Beach or bicycle to the Pinellas Trail. This area has so much to offer with beaches, trails, restaurants, fairs, etc

I've stay here a few times and it's very consistent. Perfect walkable location and very clean and comfortable. Thank you.

This place is a true gem. The lovely town has plenty to offer without being overrun with tourists like many of the surrounding areas. The beach itself its breathtaking with a spectacular sunset every night. And the actual beach cottage is phenomenal, intimate but perfectly sized for a couple or family looking for a beach oasis escape. We could not recommend it enough. Thank you!