Discover a selection of 5,000 vacation rentals in Siesta Key, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $150 per night, and houses and condos are popular options for a stay in Siesta Key. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Siesta Key
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Destination guide

Island paradise at Siesta Key vacation home rentals

Siesta Beach is regularly hailed on lists of the very best in the United States. It strings along Florida's Treasure Coast, fringing the edge of Siesta Key like a wisp of white cloud that's lapped by a sky-blue sea. But the sands aren't the only draw. This barrier isle is also a fun-loving family hotspot, laden with coffee shops and oyster bars, kayak rentals and turtle sanctuaries. Siesta Key vacation rentals cover all sorts, whether you're after a pad overlooking the waves of the Mexican Gulf or a modern apartment that takes the whole crew.

Things to do

Attractions near your Siesta Key summer rental

There's no doubt about it – the main attraction of Siesta Key is Siesta Beach. That long stretch of sand so white you might just be tempted to spoon it into your morning coffee is regularly hailed as one of the most beautiful in the whole United States. With its aquamarine waters and undulating dunes, it says, "Move over, California!" You could even bag yourself a Siesta Key vacation rental with views over the shoreline, just to make sure you're the first laying down the towel, come morning.

Activities

What to do near Siesta Key vacation rentals

Wobbling on a paddle board or blowing bubbles from a snorkeling tube, whizzing on personal watercraft or carving wakes through the Gulf – all sorts of aqua fun is on the menu in Siesta Key. Home to boating outfitters, big fishing tourers, kitesurfing guides and turtle conservationists, this Floridian island is the place to be if you love making a splash. Dolphin cruises and whale spotting usually top the menu for families. A meeting with bottlenoses and beaked whales is all but guaranteed, between December and February.

Weather

Something tropical in Siesta Key

The palms and Caribbean-esque sands of Siesta Key should be a clue to the island's tropical nature. Enjoying year-round warmth and 100s of days of sunshine, there's never really a time when the board shorts and bikinis aren't needed. Loads of people will head down during the US winter. Temperatures average around 62–74 between December and March, and there's hardly any rain at all – you'll get a tan while the snows fall in the Midwest. Summer, from June to September, is the hottest time. It also brings more chance of rain and the occasional tropical storm.

Natural features

Reefs and resplendent sands along Siesta Key

The whole coast of Siesta Key is a patchwork of cotton-white powder and turquoise seas, and a playground for lovers of the beach. You can laze on the brilliant white sands or snorkel through crystal-clear Gulf waters. Talking of the Gulf, there are coral reefs and multicolored fish waiting just off the shore, not to mention pods of whales and dolphins. You can also encounter rare turtles on the appropriately-named Turtle Beach. Alternatively, book your Siesta Key vacation rentals inland, to kayak through Floridian mangroves and creeks.

Beaches

Best beaches near Siesta Key vacation homes

The beaches of Siesta Key are its biggest draw. Vacation homes are available near beautiful beaches like Siesta Key Beach, a beach of white quartz sand with clear water, playgrounds, and tennis courts, and Crescent Beach, a wide, sandy beach on the Gulf of Mexico with picturesque views. You’ll also enjoy Sarasota Beach, a quiet beach with calm waters perfect for families.

How to get there

Transportation to and around Siesta Key

The nearest airport is in Sarasota-Bradenton Intl. Airport (SRQ), located 7.8 mi (12.5 km) from the city center.

Family friendly

Family activities near Siesta Key vacation rentals

Siesta Key is filled with unique attractions for kids of all ages. Vacation rentals are available near places like South Lido County Park, a waterfront park with swimming, kayaking, bird watching, and trails, and Turtle Beach, a sandy beach with a native population of sea turtles. You’ll also like Livingston’s Amusement Center, a colossal family-friendly activity space with go-karts, billiards, and games, as well as a bar for adults.

What are the top vacation rentals in or near Siesta Key?

Chic villas, quirky treehouses and cozy cottages — everyone's dream getaway is different. Whatever you're into, you're sure to find something you love among these top vacation rentals in Siesta Key:

  • "A Bayside Treasure - Outstanding Waterfront Views": This Gulf Coast rental comes with 2 bedrooms and is rated highly among visitors. Amenities such as an ice maker and a heated pool will help you feel right at home.
  • "Cleaned To New Standards: 4bedroom": Stay a week or so at this escape in Siesta Key Village and you'll have access to a dishwasher, a fenced pool and more. It has 3 bedrooms to accommodate your favorite people.

For even more great options, use the search bar at the top of the page to find the perfect Siesta Key vacation rental for you.

What are the best tiny house vacation rentals in or near Siesta Key?

Punching way above its weight when it comes to charm and character, a tiny house vacation rental in Siesta Key provides a front-row seat to big adventure. Shut off all your gadgets and switch your focus to nature at one of these pocket-sized escapes:

  • Leave the everyday behind and disappear to "Mystic Sea Tiny House 4 Min To The Beach". This retreat in Englewood packs plenty of conveniences into its small space, such as nearby ecotour services and air conditioning.
  • "Pinecraft Tiny Home 2 - New, Cozy And Clean" offers plenty of conveniences, including air conditioning and a TV. Located in Southgate, you'll be able to live large in this small yet comfy home.

What are the top-rated vacation rentals for weekend getaways in or near Siesta Key?

Forget about catching up on chores, because weekends were made for fun. Book one of these weekend getaways in and near Siesta Key and enjoy all the terrific things to do nearby:

  • Located 1 mile to the southeast of central Siesta Key, "Cleaned To New Standards: 4bedroom" is a favorite among adventurous types and nature lovers. Stay busy by exploring nearby attractions, such as North Jetty Beach and River Run Golf Links. If it's activities you're interested in, try water skiing or sailing.
  • Alternatively, enjoy a slower pace of life at "Waterfront Hideaway On Siesta Key In Sarasota". Approximately 4 miles southeast of Siesta Key, fun activities around here include kayaking and parasailing. More into sightseeing? Make a detour to Lemon Bay Park and Caspersen Beach.

Can I find studio apartments for rent in and around Siesta Key?

Usually compact, inexpensive and conveniently located, it's hard not to succumb to the charms of a studio apartment. Make yourself comfortable in one of these vacation rentals and get acquainted with Siesta Key up close:

  • Explore the world around you from "Living The Dream Lido Available In October". This property is an excellent base for seeing the sights and comes with amenities including a restaurant dining guide and a free nearby fitness center.
  • "Cleaned To New Standards: Gorgeous Cottages Steps From Beach" is another top choice. Get comfy and take advantage of a garden, an outdoor pool and more.

When it's time to step outside your studio apartment and discover the highlights, there's plenty to keep you occupied around Siesta Key. Into culture? Pencil in a visit to Historic Spanish Point and Asolo Theatre for the Performing Arts.

Can I find short term rentals in or near Siesta Key?

You can. Vrbo's short-term rentals in Siesta Key provide an excellent alternative to your typical cookie-cutter hotel room. Offering many creature comforts of home, you'll be able to switch into vacation mode the minute you arrive. Try one of these fantastic rentals on for size:

  • Conveniently situated close to favorite attractions like Sarasota National Cemetery, "Living The Dream Lido Available In October" will make an ideal home away from home during your short stay in Siesta Key.
  • "Cleaned To New Standards: Gorgeous Cottages Steps From Beach" is another fabulous property that welcomes short-term guests. Make the most of your swift visit by exploring local hot spots, including Venetian Golf and River Club.

What are the best romantic weekend getaways in or near Siesta Key?

Whether spent in a cottage, a cabin or a condo, a romantic weekend getaway is one of the best ways to spice up your love life. Whisk your special someone off for a couple of leisurely days at one of these sought-after escapes in or near Siesta Key:

  • Put on some soft music and slow dance the nights away at "A Bayside Treasure - Outstanding Waterfront Views". Around 2 miles from Siesta Key, this property has everything you need for a romantic weekend getaway, including a resort and a nearby bay.
  • Another place where you can enjoy a few glorious days together is "The Casa Coco | Coronado: Updated Home". Located 19 miles from Siesta Key, a nearby bay and beauty services add to the atmosphere here.

What are the best large group vacation rentals in or near Siesta Key?

Big groups mean big fun. They also mean finding a place that'll easily fit your entire crew. Check out our large group vacation rentals in or around Siesta Key and get everyone together under the one roof:

  • A range of amenities including a swimming pool and a water park make "Contemporary Beach House, 5bd, 4 Bath" a top pick. This spacious property has 5 bedrooms and sleeps up to 12 people. From the heart of Siesta Key, it's around 20 miles away to the southeast.
  • Invite up to 16 of your best friends to "Tropical Oasis - Private Heated Pool" and fill its spaces with love and laughter. This popular option has 7 bedrooms and is around 0.1 miles to the west of central Siesta Key. It's crammed with features to keep your group occupied, including a swimming pool and a kitchen.

Are there large vacation rentals that sleep 30 or more in or near Siesta Key?

Now and again you just want to get away from it all … with, oh, 30 or more of your nearest and dearest. Whether you're searching for someplace to stay with the extended family or you're planning a big ol' shindig, we have large vacation rentals in and around Siesta Key that'll house your whole party:

  • "Siesta Key Bungalows - On Water": With 10 bedrooms housing up to 40 people, there's room enough for all. You and your guests will have access to amenities including a water view and a kitchen.
  • "8 Steps To Beach Path Of #1 Beach In The Country": Offering privacy, space and comfort, this impressive home houses as many as 32 people in its 8 bedrooms. A kitchen and a garden will help keep your team content.

What are the best houses for rent with a pool in or near Siesta Key?

A pool is often an all-important amenity when choosing where to stay, especially if you're bringing the kids along. Browse these houses with a pool in or near Siesta Key and spend your days splashing about:

  • Treat the gang to an unforgettable break at "Siesta Breeze Beach House: 3bed". There's a lot to love about this escape besides its pool, such as coffee and tea making facilities and a toaster.
  • Alternatively, enjoy a change of scenery at "This House Is A 3 Bedroom - S - , 2 Bathrooms". Along with an invigorating pool, you'll also have use of cable/satellite TV services and a TV.

Siesta Key has a humid subtropical climate, with average summertime temperatures fluctuating between 80 ºF and 90 ºF. But you don't have to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the ideal Siesta Key vacation rental and organize your getaway for any time of year.

What are the best large family vacation rentals in or near Siesta Key?

You'll always have more fun sharing wonderful times with the ones you care about the most. Whether you're organizing a family trip or taking time out with good friends, Vrbo has a large vacation rental that suits you. These are two of our best in and around Siesta Key:

  • Get everyone together at "Cleaned To New Standards: 4bedroom", which has 3 bedrooms sleeping up to 7 guests. This escape is around 1 mile to the southeast of Siesta Key and features amenities such as a garden and coffee and tea making facilities.
  • Another top choice is "Beach Front 3bedroom 2 Ba Villa Near Siesta Key Village". This property is 0.1 miles west of Siesta Key and features a DVD player, a nearby laundromat and more. With 3 bedrooms accommodating up to 8 people, you won't need to leave anyone off your guest list.

When it's time to leave the house and explore, there are loads of family-friendly attractions in the area to keep everyone entertained. St. Armands Circle, Sarasota Jungle Gardens and Mote Marine Laboratory & Aquarium should be at the top of your agenda.