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Find Vacation Rentals in Siesta Key

Siesta Key
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Popular Siesta Key Vacation Rentals

Find the perfect Siesta Key vacation rental

House Siesta Key
e.g. 11/13 - 11/20 (Sun - Sun)
$130 per night
House ∙ 6 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Details
HomeToGo
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Apartment Siesta Key
e.g. 8/6 - 8/13 (Sat - Sat)
$189 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
Details
HomeToGo
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House Siesta Key
e.g. 8/13 - 8/20 (Sat - Sat)
-52%
$497
$240 per night
House ∙ 4 guests ∙ 1 bedroom
4.2
"Very good" (44 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
HomeToGo
Details
Condo Siesta Key
e.g. 9/17 - 9/24 (Sat - Sat)
-39%
$345
$210 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.4
"Very good" (8 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Details
HomeToGo
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Condo Siesta Key
e.g. 9/17 - 9/24 (Sat - Sat)
-30%
$318
$223 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.6
"Outstanding" (9 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Details
HomeToGo
Details
Condo Siesta Key
e.g. 8/13 - 8/20 (Sat - Sat)
-33%
$335
$226 per night
Condo ∙ 8 guests ∙ 2 bedrooms
4.8
"Excellent" (9 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Details
HomeToGo
Details
Villa Siesta Key
e.g. 8/6 - 8/13 (Sat - Sat)
-26%
$662
$490 per night
Villa ∙ 6 guests ∙ 3 bedrooms
4.0
"Very good" (9 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
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Condo Siesta Key
e.g. 12/3 - 12/10 (Sat - Sat)
$204 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
Details
HomeToGo
Details
Condo Siesta Key
e.g. 9/17 - 9/24 (Sat - Sat)
-29%
$537
$380 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.8
"Excellent" (10 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Details
HomeToGo
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Vacation rentals and apartments with air conditioning

House Aircondition Siesta Key
e.g. 11/13 - 11/20 (Sun - Sun)
$130 per night
House ∙ 6 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Aircondition
Details
HomeToGo
Details
Apartment Aircondition Siesta Key
e.g. 8/6 - 8/13 (Sat - Sat)
$189 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
Aircondition
Details
HomeToGo
Details
House Aircondition Siesta Key
e.g. 8/13 - 8/20 (Sat - Sat)
-52%
$497
$240 per night
House ∙ 4 guests ∙ 1 bedroom
4.2
"Very good" (44 ratings)
Siesta Key, Sarasota County, Florida, United States
Aircondition
Details
HomeToGo
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Vacation rentals with Wi-Fi

Condo Internet Siesta Key
e.g. 9/17 - 9/24 (Sat - Sat)
-39%
$345
$210 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.4
"Very good" (8 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Internet
Details
HomeToGo
Details
Condo Internet Siesta Key
e.g. 9/17 - 9/24 (Sat - Sat)
-30%
$318
$223 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.6
"Outstanding" (9 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Internet
Details
HomeToGo
Details
Condo Internet Siesta Key
e.g. 5/18 - 5/25 (Wed - Wed)
-38%
$335
$207 per night
Condo ∙ 8 guests ∙ 2 bedrooms
4.8
"Excellent" (9 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
Details
HomeToGo
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Vacation Homes With Terraces

Villa Balcony/Patio Siesta Key
e.g. 9/17 - 9/24 (Sat - Sat)
-26%
$662
$490 per night
Villa ∙ 6 guests ∙ 3 bedrooms
4.0
"Very good" (9 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
Details
HomeToGo
Details
Condo Balcony/Patio Siesta Key
e.g. 12/3 - 12/10 (Sat - Sat)
$204 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
Details
HomeToGo
Details
Condo Balcony/Patio Siesta Key
e.g. 9/17 - 9/24 (Sat - Sat)
-29%
$537
$380 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.8
"Excellent" (10 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Balcony/Patio
Details
HomeToGo
Details
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Frequently Asked Questions

What is the price of vacation rentals in Siesta Key?

The price per night in Siesta Key starts at $168.

Is there a wide selection of vacation rentals in Siesta Key?

You can find 3,234 available vacation rentals in Siesta Key.

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!

Popular Day Trips Near Siesta Key

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