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Siesta Key Cottage Rentals & Holiday Homes

Find the best cottages in Siesta Key - We found 85 exact matches

About Siesta Key Cottage Rentals on PickleTrip

Searching for cottages to rent near Siesta Key? PickleTrip™ features more than 85 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Siesta Key have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Siesta Key.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

PickleTrip™ boasts of 85 holiday cottages and places to stay in Siesta Key. The site provides unique Airbnb, VRBO, pickleball-ready cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday — all fitting within your budget.

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Frequently Asked Questions About Siesta Key Rental Cottages

There are a lot of options in Siesta Key. If you plan on staying in the Siesta Key area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Siesta Key:

The average cost for a cottage rental in Siesta Key is $535 per night. PickleTrip has a wide list of great cottages near Siesta Key that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Siesta Key that allow you to bring your pet:

See all pet-friendly vacation rentals in Siesta Key on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Siesta Key to find one that works for you.
As of 2026, the data from PickleTrip shows that there are Over 85 private swimming pools or cottages with indoor pools in the Siesta Key area along with other great amenities.
About 85 cottages in Siesta Key boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Siesta Key on PickleTrip
Yes, there are luxury cottages in Siesta Key. Find more luxury, lakefront, winter, & last-minute cottage rentals near Siesta Key.