Siesta Key Condos & Vacation Rentals

Our Favorite Vacation Rentals in Siesta Key

  • Siesta Key Beach Home
     Country House
    Booking.com
    From
    $1,485
  • 2.5 Miles from the #1 Beach in the US, Siesta Key!!
     3br Home/Apartment
    HolidayLettings
    From
    $601
  • Beach Getaway Mi to Siesta Key
     Country House
    Booking.com
    From
    $321
  • WALK to Siesta Beach from this vacation paradise!!
     3br Home/Apartment
    HolidayLettings
    From
    $462
  • Amazing Hacienda Style Villa - Very Close To Siesta
     3br Country House
    HolidayLettings
    From
    $631
  • Fantastic Mansion + Chef, Chauffeur, Massage Therapist, Bar Tender, Maid, 24/7
     6br Home/Apartment
    HolidayLettings
    From
    $4,130
  • Tropical Beach Vacation - Sleeps 16
     4br Home/Apartment
    HolidayLettings
    From
    $662
  • Cosy cottage close to Downtown Siesta Key Beach and Golf courses
     Home/Apartment
    HolidayLettings
    From
    $161

Check prices for these upcoming dates

Siesta Key Vacation Rentals with a Pool

  • Crossing the street to Siesta key beach entrance.
     7br Home/Apartment
    Airbnb
    From
    $2,857
  • Tropical Beach Getaway - 4 minutes to Siesta Key
     3br Home/Apartment
    Airbnb
    From
    $1,259
  • Extraordinary3BRDenBeachfrontLuxuryVilla+Amenities
     3br Home/Apartment
    Airbnb
    From
    $1,336
  • Luxury House - Pool Spa- Short Walk to Siesta Key
     5br Home/Apartment
    Airbnb
    From
    $1,337

Siesta Key Vacation Rentals with Wi-Fi

  • Tropical Beach Escape Near Siesta Key Beach - Sleeps 6
     3br Home/Apartment
    Airbnb
    From
    $1,259
  • Tropical Beach Getaway - 3 Mi to Siesta Key
     3br Home/Apartment
    Airbnb
    From
    $1,076
  • Tropical Waterfront Oasis Near Siesta Key Beach - Sleeps 12
     3br Home/Apartment
    Airbnb
    From
    $1,104
  • LIDO KEY: 1 BR apt walk to beach-St. Armands
    GoodHome/Apartment
    Airbnb
    From
    $423

Siesta Key Pet-Friendly Vacation Rentals

  • Great Location and Best Price
    GoodHome/Apartment
    Airbnb
    From
    $94
  • Close so siesta key and downtown sarasota!
     Home/Apartment
    Airbnb
    From
    $170
  • WATERFRONT, BEACH, FISH, GULF, PRIVATE, sleeps 11
     3br Home/Apartment
    Airbnb
    From
    $392
  • Farmhouse Charm @ Sun-n-Fun nightly or long term
    ExcellentHome/Apartment
    Airbnb
    From
    $287

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.

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.

The Weather in Siesta Key

Rainy days
84° 40°
3
87° 46°
2
86° 45°
1
94° 56°
2
97° 67°
2
99° 73°
6
94° 71°
14
96° 72°
13
96° 69°
2
94° 71°
3
91° 51°
1
84° 48°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Siesta Key. The hottest month in Siesta Key is July, when temperatures peak at 99 ˚F. The coolest month is December, when temperatures drop to 40 ˚F. The wettest month in Siesta Key is June with 13.92 inches of rain, while the driest month is February with 0.53 inches of rain.

What Expert Travelers Think

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels

Vacation Rentals in Siesta Key

Find the perfect rental for your vacation at AllTheRooms.com. We aggregate Airbnb, RedAwning, Priceline and others. We have 9,204 vacation rentals, hotels and other accommodation types in Siesta Key ranging from budget options to luxury places to stay. For those traveling on a budget, the most economical place to stay in Siesta Key is available at $11 per night. On average, an accommodation in Siesta Key will cost you $356 per night.

If you want to stay connected during your vacation, then you can choose from over 2,121 accommodations in Siesta Key that have WiFi. We have 37 accommodations that include a breakfast included. Choose from 406 places to stay that provide gym facilities, so you won't miss a single workout. Driving to Siesta Key? Then choose one of the 1,985 places to stay that comes with a parking spot included. We have 1,820 places to stay that have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to choose one of the 300 pet-friendly accommodations available.

AllTheRooms compares vacation rentals, hotels and other unique accommodation types from many providers in Siesta Key, including 1,792 places to stay from Airbnb, 421 accommodations from RedAwning and 33 places to stay from Priceline

3,090 of the accommodations in Siesta Key have been reviewed and rated. 29% are rated excellent or good. 3,066 accommodations allow instant booking.

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