Cottage holiday rentals in Casey Key, Florida

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!

A very cute, comfortable, clean and exceptionally appointed cottage. Brian is a wonderful host. We really enjoyed our stay there and look forward to visiting again. The SOS facility is a great place for family stays and is a major plus as well.

Great stay on Bokeelia! Tina’s place is beautiful, perfect for a stay-cation. The sky views at night were incredible and the hot tub was perfect. Highly recommend!

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.

This is a BEAUTIFUL place. There was a lovely welcome basket with toiletries when we arrived. Lots of fun board games. The back patio with hot tub are incredible, at night it is amazing. The host was really proactive in communicating with us, and was a pleasure to work with. Very, very quiet inside as well. With 2 bunk beds in the 2nd bedroom, you have lots of options. My son kept begging us to stay another day! We would highly recommend this location to anyone.

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!

I was so pleased with my little cottage. Very clean and all the little details were there to make my stay comfortable. Located in a quiet neighborhood. I felt very safe. A good location to grocery store, restaurants and beaches. A very short walk to a wonderful Mexican restaurant, Paraiso. Angelika can often be found outside in her vast garden areas. Told me to help myself to her tomatoes! Met her husband Al who was also very pleasant and friendly. I liked the fact they lived next door. Although located off a busy street it is quiet and can’t even be seen from the street due to all the large foliage that surrounds it. I would definitely recommend this to a single person or couple who want a comfortable place to stay and easily accessible to wherever you may want to go.

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.

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!!

Absolutely amazing place!!! 2 minute walk to the beach, spacious living area with a big open kitchen, stocked with everything you would need. The owners thought of every little detail! The gardens are the envy of the neighborhood and the spacious community area with the huge fountain is lovely. Very quiet, even with the post hurricane construction going on (at time of our visit they were still finishing up some of the units). We can’t wait to come back!

We had a great time at this villa! The pool was amazing. The backyard was peaceful. We loved that we could bring our dog with us. 2 minute walk to the beach. Would definitely love to stay here again.

Perfect little get away! Had everything we needed and just a quick walk to the beach. Loved the outside patio in the evenings!

Absolutely loved our stay! The place was beautiful, clean, and exactly as described. It’s literally less than a minute walk to the beach—such a perfect location. Quiet, peaceful, and a great little getaway spot. The host had everything we needed, which made the stay super comfortable and convenient. Couldn’t have asked for a better place to relax and unwind. Highly recommend!

This tini home is great! We had two very nice days - the area is super calm! Out neighbour was a gator - so don’t go for a swim 🫢🙂

Great location, beautiful sunrise, great fishing! My daughter cast out and within five minutes, caught a bass!!

Our stay at the cottage was perfect. The place was equipped with everything you would need to feel right at home. Carol, the host was responsive and helpful with so many amazing recommendations.

We had a great time staying here! The home was beautiful with all the beach supplies one could want. As someone who drove their boat up, the dock had great cleat availability and we had no problems getting a spot. One of the easier places to dock at that I have stayed overnight. Home also has everything for cooking and good wifi for being on an island. Loved the vibe of LGI, watching the sunset, and exploring the surrounding islands. Would definitely stay again!

This was a great stay and I would come back!

I travel regularly for work. I’ve stayed at dozens of AirBnbs throughout the country. This was my best experience by a mile. I was legitimately sad to leave. Can’t recommend this spot enough!!!

The place was even nicer than expected! It was well located and perfect for two people with separate bedrooms and bathrooms. The beds were very comfortable which was awesome! We loved sitting out on the little patio in the morning. Keep in mind that you will need to buy all perishables including olive oil, spices, etc...that was listed under the instructions that they included prior to our stay...just a heads up. Also, the cute space was immediately around the corner from, Salt...we recommend if you're interested in a nice dinner out. We were very happy with our choice and would definitely stay here again!