The Cottages On The Key - Siesta Key, Florida

Erika Cantafio

My husband and I are from NEPA, and had booked a 2 week stay for our beach wedding on 11/22/24. After the hurricanes there was damage to the home we originally booked with this company, leading to a cancellation on the home owners part. The team at Cottages On The Key worked ENDLESSLY on finding a new home for us and our guests. I could not be more grateful for Charles and his co workers who helped save our wedding. We stayed at Bali Hai House and it was absolutely beautiful. We were welcomed with customized wedding cupcakes, a bottle of champagne, and a vase of roses! I can go on and on about how perfect this vacation was. We cannot wait to book with this company again for our vacation next year.

Annie Meyer

We’ve been vacationing on Siesta Key for over 30 years and have rented from (what seems like) every rental company.

Without a doubt, Cottages on the Key is the best team we’ve worked with. They’re very professional, incredibly responsive and have a level of hospitality (and attention to detail) that feels rare these days! This is true not just upon booking, but throughout the duration of the stay. RECOMMEND!

Catherine Wolff

We stayed in the Casita Morning Star and we will definitely be back. This was our first time renting with cottages on the key and they did not disappoint. There were cupcakes waiting for us when we got there for my son’s birthday, the rental was fully stocked with everything you would need for the beach/pool, fully stocked kitchen, toiletry kits in each bathroom, and their management team was very quick to respond to questions/concerns. Thank you for a great vacation!

Raffy D.

Wow! Wow! Wow!
We rented Bali Hai House from this property management.
The house was well kept. It was also well stocked with toiletries, paper goods, kitchen supplies and best of all enough beach and bath towel to use once per day for 2 weeks!!! The house also included beach chairs, umbrellas and Cabanas!!! Definitely saved us money from renting!!
We have been booking with VRBO and been disappointed. After booking with The Cottages on the key, I do not know if we can ever find a better property management group!!
The communication was top notch! Dennis, helped me from day one. He was polite, professional, knowledgeable of the area and friendly. He was not pushing or acted like a salesman but rather assured that all my questions and concerns were answered accordingly. We received an email and text message to assure we have all the appropriate information. We were informed to check in early!! This was a plus since we arrived at Siesta keys a few hours before the 4pm check in. We needed something during our stay. My text messages were answered promptly even though it was 1:00am!! It was assuring to know that if we needed anything, the team members were there to help us!!
Would definitely use this team to book our next trip! Thank you Dennis and team!!!!!!! Talk to you next year!!!!

Christina Hills

We had such a great time at our cottage in the siesta keys!

Part of what made this so great was the excellent management team of the property. They were very responsive and kind and helped us if we needed it.

The next time we come we will certainly book through this company. They are the best!

Angela Stier

Wonderful family trip for 3 teenagers for first timers to Siesta Key Beach. Love this place!! Very clean!! Beautiful setting on the beach. Close to everything in Siesta Key. Great communication to get in before our booking. Staff was very attentive to our needs. We didn’t want to leave. Would definitely book there again! Highly recommend!!

Jo Lewis

We rented Villa Vista Mare on Siesta Key Beach and we were not disappointed. This condo is beautiful and well appointed. Anything a vacationer needs is provided ( beach towels, beach chairs, beach caddy, bikes, laundry detergent, etc. no detail was missed). There is a direct view of the ocean from this unit and it is right near beach entry point #11. There is a nearby trolley stop, so you can take the free trolley into the "downtown" area for the restaurants and gift shops. We opened the huge accordion doors to the balcony and enjoyed the ocean air most mornings. The balcony is large enough to sit 4 comfortably and is great for watching the boats of the people going up and down Beach Rd. While we were there, we saw Santa come by on a Harley Davidson! Hahahahaha! It was just a super short walk and we were on that famous white powder sand of siesta key. The beach here is huge so keeping socially distant was a breeze. The building has a private pool and grill. There is also an elevator! The unit itself was beautiful and tastefully decorated. The kitchen is stocked with all of the household necessities. The beds were fabulous. This place is huge and had plenty of room for us to spread out. Cottages on the Key staff stayed in touch and made needed suggestions. When we arrived there was a spread of delicious cupcakes and wine to welcome us. What a nice touch! NOTE: There is a guest book on the bar area, so don't forget to leave a few words for fellow travelers. I took my mother and daughter for a holiday getaway to recharge and we were better for it, thanks in part to this beautiful place! This is a wonderful condo in a wonderful location and we can't wait to visit again.

Pensee Do

Our family had a great time staying at the Monarch Villa in Siesta Key. The house was very clean and the location is awesome, just cross the street to reach the beach access. Loved the structures of this house especially the balconies. We could see the beach on the top balcony of the master bedroom. One of the toilet was broken but repair was very quick within 1/2 hr. The pool was shared but we didnt have any problem. We loved how all detergent and handsoap were provided for the dishwasher, the washer and the kitchen sink, and all bathrooms, unlike some of the properties we stayed in the past. There are plenty of beach towels. We would highly recommend this property and would love to stay here again in the future.