Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village

The host was amazing. Always very responsive and quick to get us what we needed. The house itself was beautiful. Perfect location.

Nice house within walking distance of the beach and the town. Host was a good communicator.

This is a fantastic Siesta Key location. You are steps from the beach and steps from downtown. There is more than enough room for everyone in your group to spread out and enjoy themselves. We rented both 113 and 117 to have one huge space that sleeps 20+. It was so great for everyone to have their own rooms, and we loved the pool area. The rental even boasts elevators as well which is a huge benefit! Lots and lots of beach chairs in each unit (and nice chairs, not the typical old and rusted ones that you typically encounter in most beach side rentals). Siesta Key is such a great spot for a big group as there is plenty to do for everyone - the beach, shopping, sports bars, great restaurants, tennis/pickle ball, etc... You won't regret booking this rental home and even more so if you bring a big group and get both side by side units!

Fantastic property in a perfect location. Within easy walking distance to a (basically) private area of the beach, and a very short walking distance to great restaurants and shopping. The home itself was better than we ever expected. Terraces off of almost every room and a nice pool with fabulous amenities. I can't say enough great things about our stay there. All communication with the property manager was also fabulous and he replied VERY promptly to my questions (which were very minor, but he was always very gracious and quick to respond). Love this place and hope to return!

There were so many things that we loved about this home. There were 7 of us in our group and we were more than comfortable. We did not need anything but our clothes, food and sunscreen. The location of this property is the best! Walking distance to our favorite restaurants, mini grocery store and shopping. We used the trolley for sightseeing and trying an ice cream shop at Crescent Beach. I was surprised by the fact there were two wagons, beach chairs for everyone (plus more we didn't need) and two umbrellas for the beach. Our grandson loved the pool!

This is my second time renting with Dan, part of the Gertrude family, and each time my experience is better. They make sure your vacation is perfect and that your family enjoys it to the fullest without worries. If you have any problems or concerns, just call them and they will take care of fixing it so you can continue enjoying your vacation. Dan is an excellent person. He explains everything and is always there if you need him. I have traveled a lot to other places, but with Dan, I feel like my vacation is guaranteed and that it will be 5-star. I recommend it and you will not regret it with the attention from Dan and his team. I also emphasize that the houses are very clean and very beautiful with the decoration. Many thanks to Dan and his team for their attention and dedication to make my vacation unforgettable.

The house is perfectly located by the beach and the main strip, the host was very helpful and accommodating!

We do this every year same group same weekend. We wanted to make it special for our 50th birthday celebrations!! (We’ve been friends a long time.) the house was perfect for going to the beach or hanging out in the village. Plenty of rooms greet areas for gathering. (We are between 7-10 women). We’ve stayed in a lot of places this was easy and excellent. Yeah stuff broke or didn’t work right and as soon as I let them know they were right one it. Made it easy. Also the house if well equipped with all the beach things you need.

Really happy with place it was above and beyond with all it has to offer and team always ready to help with any of your necessities, they handled everything from start to finish this is really is a great place to stay and we definitely will be returning with Dan the man

Our stay at this stunning gulf-view rental was absolutely perfect! The house offered breathtaking views of the sunset right from the spacious deck, making every evening feel magical. The interior was beautifully decorated, clean, and equipped with everything we needed for a comfortable stay. The location couldn't have been better — just a short walk to the beach, local restaurants, and lively bars. It was so convenient to enjoy a day on the sand and then head out for dinner and drinks without needing to drive. The host was incredibly responsive and thoughtful, ensuring we had everything we needed for an unforgettable getaway. If you're looking for a peaceful retreat with unbeatable views and easy access to local hotspots, this place is a gem. We can't wait to come back!

We really loved this home to stay in for five nights. It was a two minute walk to the beach, two minute walk to the village. It was very spacious and clean. Unfortunately We did not have great weather to utilize all the multiple decks and the pool area. There is a great rooftop deck where we were able to see a beautiful sunset. We would definitely stay here again!

We loved this house and it was at a perfect spot. Once we got there we never had to drive, everything was in walking distance.

The stay was perfect! Great accessories for the beach, walking distance to the restaurants and bars. Beach was a short walk as well! We loved the stay and would recommend it to anyone. The elevator was a cool touch as well it made it easy to fill a cooler and bring luggage to different floors. Really great communication and even let us drop our bags off a bit early which was awesome!!

Amazing property and location!! We loved it! The parents and recent grads had a blast. Thank you!!

Easy to check in and communicate. Perfect location, pool, and rooms. We will be back! Appreciate everything!

We enjoyed our stay here very much. House was close to restaurants and the beach so we really didn’t have to drive around much. It was also nice to have a wagon to take our stuff to the beach as well as bikes to explore the area. I thought the pool was small but lots of other compensating factors.