Vacation rentals in Siesta Key

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Popular amenities for Siesta Key vacation rentals

Stay near Siesta Key's top sights

The Cottage68 locals recommend
Siesta Beach Pavillion3 locals recommend
PARASAIL SIESTA24 locals recommend
Phillippi Estate Park17 locals recommend
Siesta Key Oyster Bar167 locals recommend
South Lido Key Beach Park on the Gulf25 locals recommend

Other great vacation rentals in Siesta Key

Guest favourite

Guesthouse in Sarasota

4.93 out of 5 average rating, 454 reviews

La Casetta: "the little house" near to the beaches

Aug. 12 – 19

$152 CAD per night
Guest favourite

Bungalow in Sarasota

4.97 out of 5 average rating, 172 reviews

The Sarasota Sea Turtle Cottage

May 29 – Jun. 5

$189 CAD per night
Guest favourite

Guesthouse in Sarasota

4.93 out of 5 average rating, 105 reviews

Adorable guest house

Dec. 20 – 27

$175 CAD per night
Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 190 reviews

The Sapphire Suite 1Bed/1Bath

Nov. 7 – 14

$183 CAD per night
Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 283 reviews

Beach & Town Posh Location! Jungle Paradise Studio

Aug. 16 – 23

$279 CAD per night
Guest favourite

Guest suite in Sarasota

4.95 out of 5 average rating, 233 reviews

Sweet Hideaway Minutes from Siesta Key!

Jul. 6 – 13

$163 CAD per night
Guest favourite

Cottage in Siesta Key

4.94 out of 5 average rating, 66 reviews

Surf Shack- Walk to Village/Boat Dock Included

Aug. 15 – 22

$244 CAD per night
Guest favourite

Apartment in Sarasota

4.98 out of 5 average rating, 43 reviews

Studio Minutes to Siesta key, Lido Key, and SMH!

Jun. 6 – 13

$165 CAD per night

Quick stats about vacation rentals in Siesta Key

  • Total rentals

    1.7K properties

  • Rentals with dedicated workspaces

    770 properties have a dedicated workspace

  • Rentals with a pool

    1.3K properties have a pool

  • Pet-friendly rentals

    350 properties allow pets

  • Family-friendly rentals

    1.4K properties are a good fit for families

  • Total number of reviews

    29K reviews

Your guide to Siesta Key

All About Siesta Key

The beaches on this barrier island in Sarasota have a luxurious feel, thanks to the pure white sand along its 13 kilometers of pristine coastline. On each of the island’s three main beaches — Siesta Beach, Crescent Beach, and Turtle Beach — the sand is almost exclusively composed of tiny quartz crystals, believed to have originated in the Appalachian Mountains millions of years ago. Digging your toes into it, you’ll notice the soft sand stays cool, even under the hot Florida sun. The beaches here fade into aquamarine surf, and as you watch the sunset over the Gulf of Mexico, you’ll come to appreciate why Siesta Key Beach is such a popular destination.

This beach town has a lively vibe, especially around its main hub, Siesta Key Village. At the core of the village on Ocean Boulevard, you’ll find a variety of local shops and open-air bars and restaurants giving you plenty to do here both on and off the sand.


The best time to stay in a vacation rental in Siesta Key

Siesta Key condo rentals can fill up in the springtime when the weather is warm and dry. This is when the area has the most festivals, too, with the Children’s Easter Party and Egg Hunt kick-starting the season in late March and the Siesta Fiesta arts and crafts festival in late April. The Amateur Sand Sculpting Contest in May invites you to try your hand at sculpting Siesta Key’s renowned quartz sand. But if you want to see the masters at work, consider visiting in November for the International Sand Sculpting Festival.

The summer months are another popular time for exploring options for Siesta Key villas for rent. The afternoons are often hot and humid, and there are typically more rain showers during this time of year. However, the long days are the main draw for many vacationers. As summer gives way to autumn, rain falls more steadily on the region until wintertime, when snowbirds arrive in search of mild winter weather.


Top things to do in Siesta Key

Siesta Beach

No trip to Siesta Key would be complete without visiting Siesta Beach, the most popular of the region’s three beaches. The white sand and warm water invite lounging and swimming, while volleyball courts offer a fun activity for groups. Concession stands with food and drink make it possible to spend the entire day at the water’s edge. There’s a longstanding tradition here on Sundays of winding down the week with a drum circle during sunset.

Siesta Village

A short walk from Siesta Beach will get you to Siesta Village, where you’ll find beach-style restaurants and tropical-themed bars. The bright-coloured shops, thatched-roof huts, and towering palm trees give the small district a vibrant atmosphere, while extra-wide sidewalks accommodate window shoppers and cyclists alike.

Point of Rocks

Point of Rocks is a beginner-friendly snorkelling area with shallow, calm water. This rocky sea wall located south of Crescent Beach hosts a myriad of sea life, including gentle manatees in the summertime. High tide is the best time to explore with a snorkel and fins, while low tide offers opportunities to examine tidal pools on land.

Destinations to explore

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