Cottage holiday rentals in Longboat Key

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!

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.

We had the best time - it was everything we could've wanted in a rental! This was our first time staying in Holmes Beach and we loved it. The house is close to everything in town. We used and enjoyed all the wonderful amenities that Craig provides - the golf cart (a must!), beach cruisers, beach wagon, umbrella and chairs. The pool, hot tub and hammock were also a highlight for us. We can't wait to come back!

My friend and I recently stayed at Laura‘s place with our four kids under four years old. The house was not only super cute and clean, but also very comfortable, accommodating and kid friendly. Laura even made sure we had enough cribs/ floor beds to accommodate our specific sleeping needs for our young kiddos. Despite the chaos of juggling 4 kids, we felt right at home and welcomed by Laura. It was so nice to have plenty to “do” at the house when we chose to stay in and were within 15 minutes to beaches and shops on days we chose to venture out. Indian rocks beach was our favorite (less crowded than Clearwater - although parking took a little time to find mid day) and we had a blast at ZooTampa (~40 min away). We also walked around shops and ate lunch at Pelican Walk Plaza which was a fun change of pace. Ice cream and Walmart (and other grocery/ stores) were 2-5 minutes from the house which was super convenient as well. We highly recommend the house/ property, location and hostess!

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.

Great private stay a block from the beach and two blocks from the village. The area is very walkable for things to do and eat. If you’re looking for a honeymoon, anniversary or getaway spot this is perfect! And the hot tub is a nice touch.

We’ve stayed near Siesta key before, but the experience was very different this time due to our host. Starting before we arrived, she made sure we would have what we needed for our staff, including a high chair and crib. During our stay she checked in regularly. It felt more like we were staying at a friends house than a rental.

The cottage was very cozy and comfortable. Loved being able to walk down to bayshore for nightly walks. Also enjoyed the nice little back patio with sitting area. The weather was so nice and we ate out there many nights . Also nice to have your own driveway to park in. Would stay here again . :)

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.

I only stayed a short few nights, but the place was wonderful. The day of my check-in Lori had contacted me to let me know I could check-in early if I pleased, which was very helpful to me. She had many suggestions on things to do in the area with all the information you would need. I loved just how close it was to the beach and some wonderful restaurants, all only a short walk away. The place was very clean and had everything I needed. Can’t say enough great things about it, it’s not surprising to see it’s booked up far in advance!

We thoroughly enjoyed our stay at Canopy Cottage. This was our second year staying and loved it even more. Jami is an excellent host. We loved being close to the Legacy Trail to ride bikes and the sort drive to Siesta Key Beach! Would definitely stay again.

We had a wonderful time in Bradenton. We love the area because it has great beaches and lots to do. This home was close to the Riverwalk area which we really enjoy. There are great restaurants and just a nice area to walk around. The house itself was very comfortable for us. Becca has lots of things there for people to enjoy doing. We played a lot of ping pong and corn hole. The kitchen was well stocked and there was a grill to use. We would love to stay in this home again.

Grouper was a great cottage for a relaxing girls mini vaca! Walked over the bridge in the am for exercise, spent the day on the beach, afternoons drinking wine on the covered dock, and strolled to local restaurants for fresh fish dinners!! Perfect!!

This was the best Airbnb we have stayed at!!!! We travel alot for basketball and this was a favorite for all 9 of us. The house felt so cozy and decor was amazing. Krista was so generous and flexible with the check in/out times and process. The outside was so relaxing and peaceful, along with so much to do. We will be back!!!

We enjoyed our stay. The house was very clean and had everything we needed. It was very quiet and peaceful. Very easier to get everywhere we had to go. I highly, recommend Doug's place.

Everything was LOVELY! The kitchen was fully stocked with everything needed, much appreciated! The home was super clean and peaceful. The pool was warm and clean ... the shower outside was amazing! Our stay was truly amazing and peaceful ... a home away from home.

Staying at Shane's place was wonderful! Our family stayed for 8 nights. It was just as described, and the pictures were extremely acurate. The place was very clean and it really was just a short walk (maybe 3 minutes) to the beach. We had everything we needed for our stay. Diane was extremely helpful and responsive and she answered all of our questions in a very timely manner. The neighborhood is beautiful, quiet and very safe. Another family was staying upstairs during our stay, and although you could hear them a little bit, we had no issues with the shared access areas because they were super nice and friendly, too. The beach is absolutely gorgeous and not crowded at all. We had access to beach equipment (chairs, unbrellas, etc, which was a bonus for us). It was a perfect beach vacation for our family of 4 and we can't wait to stay at Shane's place again!

Terry was very responsive, and the cottage was exactly as described. The location was amazing, being so close to the beach, a minute walk, we were able to go back and forth to the cottage quickly. We were there over Easter break, and it was very relaxing and beach was not busy. Terry recommended Kenny’s Corner for breakfast and lunch, and it did not disappoint. Also, Nachman’s Fish Market across the street was amazing! We bought fresh scallops, little neck clams, asparagus and rice and cooked in the cottage. We also at Easter dinner at Backwaters Grill , about .04 miles away, their key Lime Pie the Butter Blackened Ribeye was amazing. Overall the trip was a success! Thank you Terry for all your recommendations and for being a great host!

Citrus Cottage 2 was the perfect size for my wife and I. The location can't be beat. Dunedin is a walkable town, and the cottage was right in the center of everything. We were a 5-minute walk to numerous restaurants and breweries and to the Pinellas Trail. Michael provided a clean and comfortable home for us to relax in. The shower was amazing and felt so good after a 13+ mile bike ride. We have been to Dunedin several times and this was, by far, the best place we've stayed in. We highly recommend Citrus Cottage 2, and we will definitely look to stay here again the next time we visit Dunedin!

This house is an absolute gem! It had everything that we (and our dogs) needed and more! There are so many wonderful spaces to relax in. We enjoyed the main room, screened in back porch, beautiful front courtyard, and sipped coffee in the back yard each morning by the canal. We also had a blast paddling out to the bay in the canoe! The host is super friendly and quick to respond. She has put a lot of nice touches on the property that we really appreciated. We had the best time here and would love to come back! Highly recommend a stay here!

We love the Sun Cottage. This is our second stay there. A really nice place. Within walking distance or short drive to the beach. Lauren responded to our questions very quickly. We stayed two months so we really appreciated the washer/dryer and the stocked kitchen. We would definitely book again.

We spent 4 days here with our 3 kids (11, 9 & 3) and absolutely loved it! The cottage is perfect for a family with small kids or a couple of adults. I wouldn’t recommend more than that because of the bathroom. They have really maximized the space & we were pleasantly surprised to see that it was a little different from the photos- in a great way! There is a counter top that wraps around in the kitchen/living area. The beach chairs were a huge bonus as half of us flew in and didn’t have much room for packing. Between the 5 of us, the house had plenty of dishes, towels, trash bags, etc.. much more was provided than your average condo/rental home stay. The neighborhood is amazing and truly a gem, rare to find such peace and quiet on a busy coast. My kids were enamored with Charlie the bird and we really enjoyed having so many walkable options for food (The Grove was our morning routine!) If you are looking in the area, do not hesitate to book this home- you’re in for a treat!

Fabulous time at hidden cove - only thing to keep in mind is there are only 2 beach chairs so if you’re with a bunch of beach bound guests that could be a consideration. Loved our stay and would definitely stay again when we want to be in the Bradenton area.