Vacation rentals in Siesta Key

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Top-rated vacation rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 471 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Nov. 14 – 21

$223 CAD per night
Guest favourite

Guesthouse in Sarasota

4.93 out of 5 average rating, 448 reviews

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

La Casetta means, in Italian, a tiny house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

Oct. 14 – 21

$164 CAD per night
Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 101 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Aug. 6 – 13

$192 CAD per night

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
Siesta Key Oyster Bar167 locals recommend
Phillippi Estate Park17 locals recommend
South Lido Key Beach Park on the Gulf25 locals recommend

Other great vacation rentals in Siesta Key

Guest favourite

Guest suite in Sarasota

4.96 out of 5 average rating, 101 reviews

Cozy little guest suite- 6 miles from Siesta Beach

Apr. 24 – May 1

$176 CAD per night
Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 298 reviews

*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*

Jan. 22 – 29

$917 CAD per night
Guest favourite

Guesthouse in Sarasota

4.93 out of 5 average rating, 363 reviews

Clean and Modern Sarasota Studio w/ Beach Gear!

Sep. 1 – 8

$162 CAD per night
Guest favourite

Apartment in Sarasota

4.98 out of 5 average rating, 164 reviews

Gillespie On The Park, Walk to Downtown

May 21 – 28

$144 CAD per night
Guest favourite

Guesthouse in Osprey

4.99 out of 5 average rating, 281 reviews

Cozy Cottage by the Bay

Apr. 7 – 14

$179 CAD per night
Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 254 reviews

Two Miles to Siesta Key

Oct. 21 – 28

$212 CAD per night
Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 196 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Oct. 15 – 22

$189 CAD per night
Guest favourite

Apartment in Siesta Key

4.99 out of 5 average rating, 136 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Oct. 26 – Nov. 2

$711 CAD per night
Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 279 reviews

Beach & Town Posh Location! Jungle Paradise Studio

Jul. 18 – 25

$274 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

Jul. 27 – Aug. 3

$240 CAD per night
Superhost

Apartment in Sarasota

4.91 out of 5 average rating, 34 reviews

Luxury Queen Suite

Aug. 18 – 25

$232 CAD per night
Guest favourite

Condo in Siesta Key

4.91 out of 5 average rating, 81 reviews

NO Stairs, beachfront & short walk to the village!

Aug. 23 – 30

$1,127 CAD per night

Quick stats about vacation rentals in Siesta Key

Total rentals

1.6K properties

Rentals with dedicated workspaces

680 properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

340 properties allow pets

Family-friendly rentals

1.3K properties are a good fit for families

Total number of reviews

28K 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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  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key