Search Siesta Key Vacation Rentals

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

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 vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Siesta Key offers 2902 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Siesta Key start at an average price of $232 a night with long-term rentals averaging $10351 a month.

These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 2729 of Siesta Key’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 2090 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 2599 vacation home rentals.

Traveling with your dog or cat? Choose from 368 pet-friendly rentals in Siesta Key that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!

Search properties from 12 vacation rental sites in Siesta Key where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 1365 HomeAway rentals, 525 TripAdvisor short term rentals and 385 Booking.com vacation rentals.