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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

  • Siesta Key Condo - on the water !
    GoodHome/Apartment
    Booking.com
    From
    $132
  • Exceptional townhouse - Royal Palm Suite - with Gulf Views from all 3 balconies
    Good3br Home/Apartment
    HolidayLettings
    From
    $460
  • The Resort At Longboat Key Club
     Boat
    NextTrip
    From
    $316
  • holiday home for max. 8 persons in Bradenton, Florida
     Country House
    TUIvillas
    From
    $368
  • Salty Dog
     Country House
    Booking.com
    From
    $484
  • $99 OCT SPECIAL! 3 min drive/15 min walk to Siesta Key! Super Clean!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $240
  • Zota Beach Resort
     Boat
    NextTrip
    From
    $263
  • Ebb Tide #1
     Home/Apartment
    Booking.com
    From
    $159
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Check prices for these upcoming dates

Siesta Key Vacation Rentals with a Pool

  • Sea Club I
    Good24br Home/Apartment
    Booking.com
    From
    $146
  • Stroll to Siesta Beach from Serene Condo + 2 bikes
    ExcellentHome/Apartment
    Airbnb
    From
    $213
  • V4 POOL Walk to Beach 1 king bed Villa 30% OFF
    ExcellentCountry House
    Airbnb
    From
    $213
  • 5mil to Beach!Pool!WiFi,SmartTv,Cable,3B/2BSleeps8
    Excellent3br Home/Apartment
    Airbnb
    From
    $274
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Siesta Key Vacation Rentals with Wi-Fi

  • Siesta Suite at Moonbeam Manor
    Excellent2br Home/Apartment
    Airbnb
    From
    $226
  • Beautiful Waterfront Florida Home
    ExcellentHome/Apartment
    Airbnb
    From
    $153
  • Luxury House - Pool Spa- Short Walk to Siesta Key
     5br Home/Apartment
    Airbnb
    From
    $1,337
  • Sunshine Paradise
     Home/Apartment
    Airbnb
    From
    $141
Show all

Siesta Key Pet-Friendly Vacation Rentals

  • Pet Friendly Pool Home Close to Beaches & Town
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $316
  • Charming 'Old Florida' one bed apartment, Sarasota
    NiceHome/Apartment
    HolidayLettings
    From
    $152
  • SMALL STUDIO APT, PERFECT LOCATION CLOSE EVERYWHERE,SIESTA (8 min), pet friendly
     -1br Studio
    HolidayLettings
    From
    $82
  • BIG HOUSE 5br/2bth/Playground walk DOWNTOWN,Beach
     5br Home/Apartment
    HolidayLettings
    From
    $278
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
92° 54°
1
89° 44°
2
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
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Siesta Key. The hottest month in Siesta Key is May, when temperatures peak at 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

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
    Kid World Citizen

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
    Visit Amanda Alston

  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
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Vacation Rentals in Siesta Key

At AllTheRooms.com we have rentals from all of your favorite providers - Airbnb, RedAwning, Priceline and many more. Siesta Key has 9,171 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. A vacation in Siesta Key can be budget-friendly - the cheapest price accommodation is available at $10 per night. A typical vacation rental in Siesta Key costs on average $366 a night.

If you want to stay connected during your trip, then you can choose from over 3,635 accommodations in Siesta Key that have WiFi. 33 of our accommodations come with breakfast in the price. Choose from 871 accommodations that provide gym options, so you don't miss a single workout. If you are driving to Siesta Key, you'll want to pick from 3,379 places to stay that provide parking. 1,700 vacation rentals come with a pool or jacuzzi

If you're traveling with a furry friend, then make sure to choose one of the 513 pet-friendly accommodations available.

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 1,770 places to stay from Airbnb, 360 accommodations from RedAwning and 6 places to stay from Priceline.

3,166 of the accommodations in Siesta Key have been reviewed by previous guests. They rated 33% as excellent or good. 3,181 accommodations allow instant booking.

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