Find Vacation Rentals in Siesta Key

Siesta Key
Anytime
2 guests

Popular Siesta Key Vacation Rentals

Find the perfect Siesta Key vacation rental

House Siesta Key 2
-44%
e.g. 9/25 - 10/2 (Sat - Sat)
House ∙ 2 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $114 $203
Vrbo
5.0/5.0
"Excellent"
Details
House Siesta Key 4
-39%
e.g. 12/5 - 12/12 (Sat - Sat)
House ∙ 4 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $115 $190
Vrbo
5.0/5.0
"Excellent"
Details
Apartment Siesta Key 6
-44%
e.g. 9/18 - 9/25 (Sat - Sat)
Apartment ∙ 6 guests ∙ 3 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $253 $450
Vrbo
4.8/5.0
"Excellent"
Details
Apartment Siesta Key 2
Apartment ∙ 2 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $109
Vrbo
4.8/5.0
"Excellent"
Details
Apartment Siesta Key 3
-53%
e.g. 11/13 - 11/20 (Sat - Sat)
Apartment ∙ 3 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $86 $181
Vrbo
4.4/5.0
"Very good"
Details
Apartment Siesta Key 4
-45%
e.g. 11/13 - 11/20 (Sat - Sat)
Apartment ∙ 4 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $116 $210
Vrbo
5.0/5.0
"Excellent"
Details
Apartment Siesta Key 5
Apartment ∙ 5 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $315
Vrbo
4.9/5.0
"Excellent"
Details
Apartment Siesta Key 4
Apartment ∙ 4 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $200
Vrbo
Details
Apartment Siesta Key 2
-30%
e.g. 9/4 - 9/11 (Sat - Sat)
Apartment ∙ 2 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $110 $158
Vrbo
4.0/5.0
"Very good"
Details
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Vacation rentals and apartments with air conditioning

House Aircondition Siesta Key
-34%
e.g. 5/29 - 6/5 (Sat - Sat)
Aircondition
House ∙ 4 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $99 $150
Vrbo
5.0/5.0
"Excellent"
Details
House Aircondition Siesta Key
-50%
e.g. 12/5 - 12/12 (Sat - Sat)
Aircondition
House ∙ 6 guests ∙ 3 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $201 $404
Vrbo
4.0/5.0
"Very good"
Details
House Aircondition Siesta Key
-53%
e.g. 9/4 - 9/11 (Sat - Sat)
Aircondition
House ∙ 6 guests ∙ 3 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $299 $636
Vrbo
4.9/5.0
"Excellent"
Details
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Vacation rentals with Wi-Fi

Apartment Internet Siesta Key
-56%
e.g. 12/12 - 12/19 (Sat - Sat)
Internet
Apartment ∙ 6 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $120 $271
Vrbo
4.3/5.0
"Very good"
Details
Apartment Internet Siesta Key
-36%
e.g. 12/5 - 12/12 (Sat - Sat)
Internet
Apartment ∙ 4 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $119 $185
Vrbo
Details
Apartment Internet Siesta Key
-19%
e.g. 9/4 - 9/11 (Sat - Sat)
Internet
Apartment ∙ 6 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $281 $348
Vrbo
4.7/5.0
"Outstanding"
Details
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Apartments and vacation rentals with a kitchen

Condo Kitchen Siesta Key
Kitchen
Condo ∙ 4 guests ∙ 1 bedroom
Siesta Key, Sarasota County, Florida, United States
from $249
HomeToGo
4.5/5.0
"Outstanding"
Details
Condo Kitchen Siesta Key
-38%
e.g. 8/28 - 9/4 (Sat - Sat)
Kitchen
Condo ∙ 4 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $282 $457
HomeToGo
5.0/5.0
"Excellent"
Details
Condo Kitchen Siesta Key
-40%
e.g. 1/2 - 1/9 (Sat - Sat)
Kitchen
Condo ∙ 6 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
from $229 $379
HomeToGo
4.4/5.0
"Very good"
Details
View more

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Siesta Key Information

About Siesta Key

Siesta Key is a small barrier island off the coast of Florida with the Gulf of Mexico on the west and Roberts Bay to the east. Only about 3.5 square miles, Siesta Key has a relaxed, suburban atmosphere that draws tourists and locals who want to get away from it all, but still have easy access to mainland amenities.

Things to do in Siesta Key

Siesta Key is best known for its warm, clear beaches. Siesta Key Public Beach, voted the 3rd Best Beach in the US by TripAdvisor users, is the most popular on the island. While this long-time favorite and nearby Crescent Beach are known for their soft, spotless sand, Turtle Beach is hailed as the perfect place for collecting shells. Surfing, volleyball, scuba diving, fishing, boating, jet skiing, and even parasailing are all beach activities available at one or more beaches on Siesta Key. Downtown hosts a wealth of dining and shopping options from family-friendly restaurants to a host of clubs and nightlife spots. Explore the island’s natural beauty with a hike, bike ride, or walk to the Point of Rocks to spot rare marine life and birds.

Siesta Key Accommodations

Even though it is an island, Siesta Key is not difficult to reach. Fly into the Sarasota-Bradenton International Airport, just 8 miles from the center of Siesta Key, and drive into town via one of the two drawbridges that connect it to the mainland. If you want to get started on your vacation right away, you can even take a ferry or boat from nearby Sarasota. Finding a vacation rental with a view or pool within your price range will not be a challenge with Tripping’s wide variety of properties available on Siesta Key!

Vacation Rentals in Siesta Key

Looking for the perfect vacation rental for your Siesta Key getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Siesta Key offers 5459 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 5130 properties with high-speed WiFi Internet, 3893 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget.
For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $8896 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Siesta Key has 5459 gorgeous homes with 702 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.
Search properties from 12 vacation rental sites in Siesta Key where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 2567 HomeAway rentals, 1016 TripAdvisor short term rentals and 768 Booking.com vacation rentals.

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