The best rentals from the top sites, all in one place

We believe finding a villa vacation rental in Siesta Key should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Siesta Key

Villa vacation rentals in Siesta Key

Staying in one of the numerous Siesta Key Villas offers you a luxurious vacation experience you wouldn’t be able to have with other vacation rentals. Whether you want to be in the hills, on the beach, or near Siesta Key, VacationRenter has a wealth of villa options for you alone, your bachelor party, or your family vacation in Florida. While villas are considered to be the upscale vacation rental, you can still manage to find yourself a villa to rent for under $159/night. However, if you really want to impress the family and/or your guests, there are 187 villas available for rent between $400 and $2,103/night.

This is your Siesta Key vacation, why not do it in the lap of luxury with a gorgeous villa to make the Florida trip truly memorable. Search above to see the 1872 available villas for rent over the next 30 days, or take a look below at some of the trending villas in the Siesta Key, FL area. Siesta Key has been a frequently searched travel destination this year and continues to grow in popularity and it’s likely because of these beautiful villas for rent. VacationRenter offers a wide selection of vacation villas from travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Siesta Key luxury homes for your next vacation.

Where is Siesta Key

Whether you're looking for a family fun day trip, a romantic getaway or a recreational wonderland, you can't go wrong at Siesta Key, an island off the shores of Sarasota, Florida, in the Gulf of Mexico. Stretching eight miles in length, this warm-weather paradise is a beach lover's dream.

Quick Guide to Siesta Key

Accessible from the mainland by two bridges, Siesta Key offers beach fun at its finest. Three different beaches deliver something for everyone.
  • Siesta Beach: Here, you can sunbathe, swim, fish, picnic or play tennis or volleyball for a full day on the sand. For water adventure, navigate the warm shallow waters along Siesta Beach by kayak.
  • Crescent Beach: If you're looking for a more serene setting, this is the beach for you. Snorkelers and divers enjoy Point of Rocks. It is an area located at the southern tip of the beach featuring colorful coral and marine life.
  • Turtle Beach: With a volleyball court and a horseshoe pit, Turtle Beach offers lots of active fun by land and sea. It also makes a great place to hunt for shells and petrified sharks' teeth.

More Home-types in Siesta Key

Siesta Key has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Siesta Key:
- Oceanfront1,872 vacation rentals
- Beach1,872 vacation rentals
- Condo1,205 vacation rentals
- Apartment1,205 vacation rentals
- House489 vacation rentals
- Villa164 vacation rentals

Points of interests in Siesta Key

Siesta Key has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Siesta Key:
- CB's Saltwater Outfitters: 1,127 vacation rentals
- Siesta Key Watersports: 805 vacation rentals
- Siesta Key Drum Circle: 694 vacation rentals
- Siesta Key Beach: 647 vacation rentals
- Siesta Key Chamber of Commerce: 402 vacation rentals