1,842 Siesta Key Vacation Rentals & Short Term Rentals

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Compare Siesta Key vacation rentals from 14 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $25 to $6900 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

Find the best Siesta Key vacation rentals with Tripping.com. Choose from 3653 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $6900 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 2437 of homes in Siesta Key offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 1797 rentals with pool or jacuzzi, or relax with the family in one of the 3147 homes with cable TV.

For all those dog lovers and cat lovers, Siesta Key offers 543 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 14 rental sites in Siesta Key where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 1618 HomeAway rentals, 831 TripAdvisor short term rentals and 775 Booking.com vacation rentals.
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