Top Siesta Key cottages - Florida

Explore Siesta Key cottage rentals

The Inn On Siesta Key

Sleeps 2 · 1 bedroom

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

Sleeps 8 · 4 bedrooms · 2 bathrooms

Top rated cottage rentals - Siesta Key

Premier Host

Wonderful Place!!

We had a wonderful time at Mermaid Cottage. It was clean and welcoming. We had all the amenities we needed and the location was easy to get to every place!! We will be back!!!

Amanda C.

Stayed Aug 2024

the beautiful Gulf of Mexico just steps away!

Wonderful location in paradise!

Small cottage perfect for a couple. We had a wonderful relaxing time. One situation which was irritating was the neighbors' parties across the road. Did not respect the time limit for noise. However the owner was quick in communicating with the owners to complain about the issue. We would go back again...

Danielle C.

Stayed Apr 2024

Perfect family retreat

Jo and Carl were incredible hosts - warm, accommodating, and incredibly responsive. They went above and beyond to make our kids feel welcome. The location is fabulous and the unit has everything we needed to cook, do laundry, and enjoy some downtime as a family. We couldn’t have asked for a better experience. It was a truly magical Christmas!

Emily B.

Stayed Dec 2023

Guest cottage is straight out of a fairy tale. All that's missing are the bears.

Premier Host

Cute Hideaway for a Couple

Private apartment in a very convenient yet private location. Unit was very well equipped- tons of towels and even enough toilet paper for our 8 day stay! The bed was very comfortable and the air conditioning and the fans kept the whole apartment very comfortable.

Linda C.

Stayed Jul 2023

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Frequently asked questions

Are there any cottage rentals in Siesta Key?

Select from 81 cottage rentals in Siesta Key that offer a restful, quiet retreat among the sights and sounds of nature. Look into cottages in popular areas such as Siesta Key Village, Aloha Kai and Bay Isle.

How much does it cost to stay in a cottage rental in Siesta Key?

A number of factors will determine the price of a cottage rental in Siesta Key, such as the size of the property and how long and when you're traveling. All you have to do is enter your vacation dates and preferences to find a cottage that fits your style and budget.

When is the best time to rent a cottage in Siesta Key?

To get your ideal cottage rental in Siesta Key, timing plays a big part. Book early and you'll have a greater range of properties to pick from, especially if you're traveling during peak seasons. You can usually find more affordable prices or special early booking discounts.

Where can I rent a Siesta Key vacation cottage with great views?

Let stress fade away as you relax and take in the beach views from your inviting cottage rental in Siesta Key. Use our filter tools to search for cottages with outdoor areas, such as a patio or deck, so you can enjoy the vistas even more.

Does Siesta Key have any lakeside cottages?

Glorious views of glistening water, the peacefulness of nature and outdoor activities are just a few of the things you can look forward to in one of Vrbo's lakeside cottage rentals. Use our handy "Location" filter and click on "Lake" to see if there are any cozy retreats in Siesta Key near the water.

What are the top things to do in Siesta Key?

Siesta Key Beach, Mote Marine Laboratory & Aquarium and Sarasota Jungle Gardens are popular attractions that'll keep the whole family busy in Siesta Key. There's nothing like travel to get everyone together, so browse our cottage rentals in this vibrant destination.

Why should I book my vacation cottage with Vrbo?

Vrbo offers customer support from booking until the end of your trip, so every aspect of your vacation is hassle-free. Plus we think our cottage rentals are pretty special — think amenity-packed stays ideal for families and charming options that are perfect for a romantic interlude. When you book with us, you can also take advantage of flexible cancellation policies and other benefits like payment and deposit protection.