1,415 Siesta Key Vacation Rentals & Short Term Rentals

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Compare Siesta Key vacation rentals from 13 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $25 to $2050 a night.

Information about Siesta Key

About Siesta Key

Siesta Key is a small barrier island off the coast of Florida with the Gulf of Mexico on the west and Roberts Bay to the east. Only about 3.5 square miles, Siesta Key has a relaxed, suburban atmosphere that draws tourists and locals who want to get away from it all, but still have easy access to mainland amenities.

Things to do in Siesta Key

Siesta Key is best known for its warm, clear beaches. Siesta Key Public Beach, voted the 3rd Best Beach in the US by TripAdvisor users, is the most popular on the island. While this long-time favorite and nearby Crescent Beach are known for their soft, spotless sand, Turtle Beach is hailed as the perfect place for collecting shells. Surfing, volleyball, scuba diving, fishing, boating, jet skiing, and even parasailing are all beach activities available at one or more beaches on Siesta Key. Downtown hosts a wealth of dining and shopping options from family-friendly restaurants to a host of clubs and nightlife spots. Explore the island’s natural beauty with a hike, bike ride, or walk to the Point of Rocks to spot rare marine life and birds.

Siesta Key Accommodations

Even though it is an island, Siesta Key is not difficult to reach. Fly into the Sarasota-Bradenton International Airport, just 8 miles from the center of Siesta Key, and drive into town via one of the two drawbridges that connect it to the mainland. If you want to get started on your vacation right away, you can even take a ferry or boat from nearby Sarasota. Finding a vacation rental with a view or pool within your price range will not be a challenge with Tripping’s wide variety of properties available on Siesta Key!

Vacation Rentals in Siesta Key

Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Siesta Key offers 3614 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $223 a night, or a long-term rental for an average price of $5140 a month.

These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 2655 of Siesta Key’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 1950 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 2603 cozy homes.

Traveling with pets? Choose from 603 pet-friendly rentals in Siesta Key for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

Search properties from 13 rental sites in Siesta Key where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 1892 HomeAway rentals, 879 TripAdvisor short term rentals and 577 Booking.com vacation rentals.