Vacation rentals in Siesta Key
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Top-rated vacation rentals in Siesta Key
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Guest suite in Sarasota
4.94 out of 5 average rating, 471 reviewsStudio 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
Guesthouse in Sarasota
4.93 out of 5 average rating, 448 reviewsLa 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
Guest suite in Sarasota
4.98 out of 5 average rating, 101 reviewsMid-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
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Siesta Key vacation rentals
Other great vacation rentals in Siesta Key
Guest suite in Sarasota
4.96 out of 5 average rating, 101 reviewsCozy little guest suite- 6 miles from Siesta Beach
Apr. 24 – May 1
Island in Sarasota
4.97 out of 5 average rating, 298 reviews*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
Jan. 22 – 29
Guesthouse in Sarasota
4.93 out of 5 average rating, 363 reviewsClean and Modern Sarasota Studio w/ Beach Gear!
Sep. 1 – 8
Apartment in Sarasota
4.98 out of 5 average rating, 164 reviewsGillespie On The Park, Walk to Downtown
May 21 – 28
Guesthouse in Osprey
4.99 out of 5 average rating, 281 reviewsCozy Cottage by the Bay
Apr. 7 – 14
Guest suite in Sarasota
4.94 out of 5 average rating, 254 reviewsTwo Miles to Siesta Key
Oct. 21 – 28
Home in Sarasota
4.98 out of 5 average rating, 196 reviewsThe Key Lime Cottage 2 miles from Siesta Key Beach
Oct. 15 – 22
Apartment in Siesta Key
4.99 out of 5 average rating, 136 reviewsSiesta Key #1 Beach, pickle ball & tennis paradise
Oct. 26 – Nov. 2
Guest suite in Sarasota
4.94 out of 5 average rating, 279 reviewsBeach & Town Posh Location! Jungle Paradise Studio
Jul. 18 – 25
Cottage in Siesta Key
4.94 out of 5 average rating, 66 reviewsSurf Shack- Walk to Village/Boat Dock Included
Jul. 27 – Aug. 3
Apartment in Sarasota
4.91 out of 5 average rating, 34 reviewsLuxury Queen Suite
Aug. 18 – 25
Condo in Siesta Key
4.91 out of 5 average rating, 81 reviewsNO Stairs, beachfront & short walk to the village!
Aug. 23 – 30
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.
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