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Siesta Key Condos & Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. Florida
  4. Siesta Key

Our Favorite Vacation Rentals in Siesta Key

  • Hibiscus Suite
     Home/Apartment
    Booking.com
    From
    $238
  • Salty Summer
     Home/Apartment
    Booking.com
    From
    $206
  • Siesta Key Beach Home
     Country House
    Booking.com
    From
    $1,485
  • Key of Siesta
     Country House
    Booking.com
    From
    $175
  • Sienna Park Apartments
     Home/Apartment
    Booking.com
    From
    $110
  • Downtown Sarasota, Best Location For Your Vacation !!!
     Home/Apartment
    Booking.com
    From
    $160
  • The Casita Amarilla Beside the Ringling Museum and the Ca'D'Zan (John Ringling Home)
     Country House
    Booking.com
    From
    $225
  • Longboat Key 66 Condo
     Home/Apartment
    Booking.com
    From
    $238
Show all

Check prices for these upcoming dates

Siesta Key Vacation Rentals with a Pool

  • Sea Club I
    Good24br Home/Apartment
    Booking.com
    From
    $193
  • Siesta Key ~ Sarasota ~ Condo
    GoodHome/Apartment
    Airbnb
    From
    $223
  • Luxury Unit Steps From the Ocean in Siesta Key
    ExcellentHome/Apartment
    Airbnb
    From
    $314
  • 5mil to Beach!Pool!WiFi,SmartTv,Cable,3B/2BSleeps8
    Excellent3br Home/Apartment
    Airbnb
    From
    $534
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Siesta Key Vacation Rentals with Wi-Fi

  • Siesta Suite at Moonbeam Manor
    Excellent2br Home/Apartment
    Airbnb
    From
    $152
  • Artsy In-law Apartment Minutes from Siesta Key!
    ExcellentHome/Apartment
    Airbnb
    From
    $124
  • Florida Charm, Boating Waterway, near Siesta Beach
    GoodHome/Apartment
    Airbnb
    From
    $239
  • Beautiful Waterfront Florida Home
    ExcellentHome/Apartment
    Airbnb
    From
    $153
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Siesta Key Pet-Friendly Vacation Rentals

  • ENITRE HOME w/ community ramp 3 miles to Siesta
    Excellent3br Home/Apartment
    Airbnb
    From
    $266
  • PARADISE RETREAT ON SIESTA KEY
    Excellent4br Home/Apartment
    Airbnb
    From
    $472
  • Siesta Orchid
     2br Home/Apartment
    Airbnb
    From
    $195
  • Your own slice of paradise with only 2 minute walk to private beach on Siesta Key! - Siesta Key 09
     3br Home/Apartment
    Airbnb
    From
    $378
Show all

Siesta Key Travel Guide

Just off the coast of Sarasota, Florida, Siesta Key boasts sandy beaches, exotic marine life and family-friendly activities. Enjoy outdoor dining, shopping and kayaking while being immersed at one of America’s best beach locations.

Things to Do in Siesta Key

Hop on a boat tour around Siesta Beach and take your chances seeing a dolphin or manatee. For something with a little more adrenaline, take a parasailing tour for great views of the bustling coastline.

Elsewhere, Point of Rocks -- shallow waters with over 100 yards of limestone ledges -- is accessible via Crescent Beach and ideal for snorkeling. Tidal pools and coral reefs fill the area and are sure to bring out the marine biologist in any visitor.

Best Time to Visit Siesta Key

Perfect for a romantic holiday or for an adventurous sports getaway, Siesta Key is popular in March for spring break or over the summer months, where temperatures can top 90.

Condos in Siesta Key

Siesta Key Florida should be on everyone's bucket list when it comes to a beach vacation. Siesta Key Beach is known for having the whitest sand in the Key area, and with the Gulf of Mexico stretching out into the distance, you'll feel like you're are in paradise. Just a short drive from Sarasota Florida, the town enjoys its reputation as one of Traveler's Choice 'Best Beaches in America'. The white quartz sand is known as the Sand of Siesta, and stretches over the public beach of Cresent Beach, creating a postcard-worthy scene.

Other fun activities include playing on the tennis court, enjoying the cafes and shops in Siesta Key Village and exploring Beach Bazaar.

Siesta Key Vacation Rentals come in all shapes and sizes to suit all budgets. Keep a look out for amazing amenities such as private heated pools, hot tubs, full kitchens, and more. Whether you want a beach house next to the white sand or a rental unit within walking distance to the town center, you’re sure to find the perfect Siesta Key condo rental.

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Price and Availability in Siesta Key

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Siesta Key tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Siesta Key tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Siesta Key is in March, while the cheapest month is in September. The most popular time to book a vacation rental in Siesta Key is in the high season in March. Siesta Key has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
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The Weather in Siesta Key

Rainy days
85° 42°
8
80° 30°
3
90° 49°
0
86° 40°
2
89° 52°
3
92° 61°
7
94° 70°
4
93° 69°
8
95° 71°
5
94° 72°
6
92° 54°
1
89° 44°
2
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Rainy days

This climate histogram shows you the weather patterns in Siesta Key. The warmest months in Siesta Key are May and July, when temperatures reach 95 ˚F. The coolest month is December, when temperatures drop to 30 ˚F. The wettest month in Siesta Key is January with 8.1 inches of rain, while the driest month is November with 0.44 inches of rain.

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What Expert Travelers Think

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Vacation Rentals in Siesta Key

At AllTheRooms.com we have rentals from all of the best providers - Airbnb, RedAwning, Priceline and many more. Siesta Key has 10,762 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. For those traveling on a budget, the most economical place to stay in Siesta Key is available at $10 per night. A typical vacation rental in Siesta Key costs on average $363 per night.

If you would like to stay connected during your trip, then you can choose from over 2,270 accommodations in Siesta Key that have WiFi. 36 of our accommodations come with breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 478 accommodations that have gyms. If you're planning on getting to Siesta Key by car, be sure to choose from 2,146 accommodations that provide parking. We track 1,806 places to stay that have a pool or jacuzzi.

AllTheRooms has 349 pet-friendly places to stay in Siesta Key, so if you're traveling with your pet you won't have any problems.

We combine a wide variety of Siesta Key accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 1,861 places to stay from Airbnb, 367 accommodations from RedAwning and 33 places to stay from Priceline.

3,223 of the accommodations in Siesta Key have been reviewed and rated. 30% are rated excellent or good. You can instantly book any of 3,384 places to stay right now.

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