Siesta Key Vacation Rentals Guide

South West FL / Siesta Key

Siesta Key Vacation Rental Guide  

Situated on the Southwest Gulf coast south of Clearwater Beach, Siesta Key is a barrier island just off the mainland city of Sarasota and attracts visitors to its world-class beach. 

Siesta Key Beach was twice named the nation's best beach with 8-miles of brilliant quartz sand and turquoise waterfront. For such a small area, this little Key is big on shopping, dining, and nightlife with waterfront amenities. Whether you're looking for a fun vacation with the kids or a romantic trip for two, Siesta Key offers something for everyone.

Siesta Key hosts a variety of festivals and events year-round like the unique Chalk Festival with 3D pavement artwork delighting visitors. There is also a Siesta Beach Seafood and Music Festival, Sand Sculpting Festival, and more that draw visitors to relax and enjoy the fun in spacious rentals. Siesta Key owners are proud of their waterfront homes and offer beautiful vacation rentals to visitors looking to enjoy what Siesta Key has to offer.


Siesta Key

Siesta Key is a barrier island located in Sarasota County, Florida with a population hovering around 6,500 people, although many “snowbirds” come to escape the winter months and create a spike in seasonal population. Famous for its white sandy beaches that stay cool to the touch, Siesta Key is also home to water recreation like kayaking and boating and attracts relaxation and adventure seekers alike. And after $21 million in renovations to public facilities including a pedestrian esplanade, lounging at Siesta Key feels like relaxing at a resort.  

Siesta Key Beach

The main draw to Siesta Key is Siesta Key Beach with its dazzling white, quartz sand and beachfront amenities. Come and lounge or spend the day strolling along the barrier island. Award winner for many years in a row as one of America's best beaches to experience, with that many awards you know it has to be great.

Crescent Beach

Located south of Sarasota Beach, Crescent Beach provides a sense of privacy and seclusion among its waterfront condos and hotels. Crescent Beach has more limited access than Siesta Key Beach but also tends to draw fewer crowds. Much of Crescent Beach is private, though there is a tranquil strip of beachfront accessible by a small parking area for visitors.

Turtle Beach

Animal lovers hoping to get a glimpse of Florida's migrating sea turtles head to Turtle Beach to see its thriving population nesting on the shore. From May 1 to October 31, the sea turtles flock to Florida's Gulf Coast to nest and make their home right on Siesta Key. With 2,6000 feet of beachfront,  visitors can come to Turtle Beach to play, have a picnic, or enjoy the children's play area.


  • There are three powdery white beaches on Siesta Key made from quartz white sand that stays cool to the touch. There’s something for everyone whether you want to relax or go kayaking in the Gulf of Mexico.
  • The Siesta Key Beach area recently underwent a $21 million renovation including an esplanade to stroll.
  • Hundreds of sea turtles return to nest each year at Turtle Beach
  • Best Suited for beach lovers and anyone looking for a relaxing vacation whether families or couples on a romantic getaway.


Siesta Key is small, but there is still plenty to do whether you want to explore the beach and indulge in water sports or enjoy some upscale shopping and dining. Here’s a round-up of some of our recommended activities on Siesta Key to curate your own wish-list of what to see and do.
  • Three major breathtaking beaches - Siesta Key Beach, Crescent Beach, and Turtle Beach
  • Smaller beaches for tranquility like Shell Beach
  • Point of Rocks outdoor attraction for fishing, shelling, and viewing birds and marine wildlife
  • Boating
  • Kayaking
  • Fishing
  • SUP boarding
  • Kiteboarding
  • Jet-skiing
  • Biking
  • Parasailing
  • Scuba diving
  • Skimboarding
  • Bodyboarding
  • Eco-Tours
  • Boutique shopping
  • Fine dining and casual restaurants


Find a gorgeous vacation rental in Siesta Key, Florida on Florida Rental By Owners website. We cater exclusively to travelers looking to communicate and book directly with the owner. There are no traveler fees for using Florida Rental By Owners website, and al owners are verified for ownership. All transactions occur directly between you and the owner. You can also read online reviews and guest experiences to ensure your vacation rental will meet (or exceed!) your travel goals.  

Do you have questions about the Siesta Key area? 

Join our  Local Facebook Travel Group and ask one of the local experts.

Traveling to Siesta Key

There are several airport options to choose from when visiting Siesta Key. Choose from low-cost airline carriers or large airlines making flights from major cities in the U.S., Europe and beyond.

Sarasota - Bradenton International Airport - (SRQ)

Sarasota - Bradenton International Airport is the closest airport to Siesta Key at just 10.4 miles away (16.8 km), or roughly a 30-minute drive by taxi or rental car. Seven major carriers including Air Canada, West Jet, United, American, Delta, Elite, and Jetblue fly into Sarasota-Bradenton International Airport. However, travelers should know that flights are not offered year-round due to the highs and lows of the tourist season, so check in advance with each carrier.

St. Pete - Clearwater Airport - (PIE)

St. Pete - Clearwater Airport is centrally located between Clearwater and St. Petersburg, and is just under 64 miles (102.9 km) away from Siesta Key. It usually takes an hour and ten minutes to get from the airport to Siesta Key. However, travelers should note this route has a toll. Low-cost airline carriers fly into St. Pete - Clearwater Airport including Allegiant Air, as well as private planes and executive jets for business travelers.

Tampa International Airport - (TPA)

Tampa International Airport is 71 miles (114.2 km) away from Siesta Key. This route includes a toll and usually takes up to 1 hour and 15 minutes to travel. Served by over 20 major airline carriers, the Tampa International Airport welcomes Delta, American, Jet Blue, United, and the economical Southwest sand Spirit Airlines.

Southwest Florida International Airport - Fort Myers - (RSW)

The Southwest Florida International Airport services many airline carriers including Southwest, Delta, American, Spirit and Jetblue. At just 89 miles (143 km) away, traveling to Siesta Key only takes 1 hour and 30 minutes from the airport.

Orlando International Airport - (MCO)

Orlando International Airport is 137 miles (220 km) away from Siesta Key. Travel time is approximately 2 hours and 13 minutes. Be careful of traffic in Orlando, it is a busy city but is also a nice stop for shopping and of course Disney and other amusement parks before arriving on the island. It also has a hotel on-site for late-night arrivals or early departures.
This airport is the second busiest in the state of Florida and services 39 airline carriers. in addition to U.S. and Canadian options, it is the best option for European flights.

Transportation on Siesta Key

Although you will need a taxi service or rental car to get from your airport of choice to Siesta Key, there are plenty of nearly-free transportation options once you’re on the island. Here’s our list of transportation options to and around Siesta Key for a successful vacation.

Conscious Cab of Sarasota

If you need a taxi around the key (or off), Conscious Cab of Sarasota is ready to deliver. Book a ride to or from the airport, or get in touch for an excursion off of Siesta Key. Call 941-306-6653 to get in touch whether you’re going on a brief journey or long-distance car transportation.

Johnny's Original Free Rides

Johnny's was the first company to offer free transportation around Siesta Key with service from Siesta Key Village all the way to Turtle Beach on the opposite end. Rides are free, but you’re expected to tip generously. The team offers rides from 10 a.m. to 2 a.m. daily. Call 941-928-9200 for more information or to set-up your free ride.

Sun Ride Pedi Cab

Sun Ride Pedicab in Siesta Key prides itself on being the only true "eco-friendly" tour and transportation service. Rides around the Key are free, but drivers expect you to tip generously. Call 941-343-3400 to get in touch with Sun Ride Pedicab.

Siesta Key Breeze Trolley

Take a charming trolley ride around Siesta Key for free with the Siesta Key Breeze Trolley. You’ll get to skip the parking or traffic battle during peak tourist season. Call 941-861-1234 for more information.  

Siesta Key Florida Monthly Average Weather Chart


What types of property can I rent on Siesta Key, Florida?

Florida Rental By Owners (FLARBO) is full of a wide variety of vacation rentals in Siesta Key, Florida including condos, cottages, town-homes, duplexes, villas, holiday and private homes. Our 2019 property selection features several homes and condos in Siesta Key. We recommend selecting a property based on your needs such as proximity to beach areas, waterfront docks, parking, wheelchair accessible, nearby attractions, and whether or not the property is pet-friendly or boat-friendly.

Should I rent a Cottage on Siesta Key?

Yes, if a cottage is right for you! Most cottages in Siesta Key offer amazing beachfront views! Some include free beach gear and many amenities such as pools, hot tubs, backyard beaches, tiki huts, fitness rooms, and ping pong tables. If this is what you are looking for, then you should rent a cottage in Siesta Key.

Should I rent a Condo on Siesta Key?

Absolutely! Siesta Key accommodations include condos which often offer unique amenities and the perfect space rather than a Siesta Key cottage or sizeable private home for example. House rentals are usually great for family vacations, larger groups or those who prefer having an entire house and outdoor property to themselves.

Can I rent a pet-friendly rental on Siesta Key?

Yes, we have a lovely selection of pet-friendly rentals in our Siesta Key inventory of homes.  We love our pets, and we are sure you do too! has many pet-friendly rentals on Siesta Key. You can use our search feature to narrow down our Siesta Key rental properties to show those that are pet-friendly.

Can I rent a boat-friendly rental on Siesta Key?

Siesta Key is the perfect place to bring your boat or rent one from a local vendor! (Florida Rental By Owners) has many boat-friendly vacation rentals with docks on Siesta Key. Use our search filters to narrow down our Siesta Key rental properties to show those that are boat-friendly .

Is Siesta Key a good place for Snowbirds looking for monthly rentals?

Yes, there are many homes and condos that rent on a monthly basis on and near Siesta Key, Florida that are perfect for longer stay guests. Don't forget to search for more options just off the island in nearby culture-rich Sarasota.

Will I pay any fees to book a property on Florida Rental By Owners?

Never! We never charge any fees to book a property on Florida Rental By Owners. And we never take a commission from an owner.  If you are looking for VRBO or Airbnb type rental or lodging accommodation why pay the extra fees? Use! We put you in direct contact with the owner or manager of the property or cottage rental in Siesta Key so you always get the best price.

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