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Vacation Rentals in Siesta Key

Find 7,232 available offers from 27 partners
Siesta Key
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Siesta Key
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Popular Filters to find the Perfect Home Rental in Siesta Key

2 Adults
Pool
Condo
4 Adults
2 Bathrooms
250 yd to water
2 Bedrooms

This month's trending homes: most-clicked rentals

Discover offers in Siesta Key that attract the most attention from other travelers

House Siesta Key
from $190
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Siesta Key with Large Patio

5.0
Outstanding (75 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $191
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Lovely Condo in Sarasota with Patio, Pool & Yard

5.0
Outstanding (2 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
from $201
per night
House ∙ 6 guests ∙ 3 bedrooms

House in Siesta Key with Grill & Pool

4.7
Excellent (65 ratings)
Siesta Key, Sarasota County, Florida, United States
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Vacation rentals and apartments with air conditioning

House  Siesta Key
Feb 8 - Feb 15
-32%
$1,946
$1,330
per night
House ∙ 14 guests ∙ 5 bedrooms

House in Siesta Key with Grill + Spectacular Views

5.0
Outstanding (6 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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House  Siesta Key
Jan 11 - Jan 18
-62%
$448
$169
per night
House ∙ 8 guests ∙ 3 bedrooms

House in Siesta Key with Ample Parking

4.4
Very good (38 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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House  Siesta Key
Oct 19 - Oct 26
-53%
$243
$114
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Sarasota with Pool, Yard & Patio

4.5
Excellent (6 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Vacation rentals with Wi-Fi

House  Siesta Key
Oct 19 - Oct 26
-65%
$870
$303
per night
House ∙ 11 guests ∙ 4 bedrooms

Vacation Home in Siesta Key with Grill & Pool

4.6
Excellent (100 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
View deal
Condo  Siesta Key
Aug 16 - Aug 23
-41%
$435
$256
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Sarasota with Grill & Pool

Siesta Key, Sarasota County, Florida, United States
Internet
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Condo  Siesta Key
Oct 26 - Nov 2
-71%
$464
$136
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Siesta Key with Outdoor Pool

3.2
(10 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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Apartments With Balconies or Patios

Apartment  Siesta Key
Sep 6 - Sep 13
-60%
$410
$164
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Lido Key with Screened-In Patio

4.5
Excellent (62 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Balcony/Patio
View deal
House  Siesta Key
May 14 - May 21
$245
per night
House ∙ 5 guests ∙ 3 bedrooms

House in Siesta Key with Grill, Yard & Patio

5.0
Outstanding (8 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
House  Siesta Key
Nov 10 - Nov 17
$400
per night
House ∙ 8 guests ∙ 4 bedrooms

Wonderful House in Siesta Key with Pool, Patio & Grill

5.0
Outstanding (93 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
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Best Vacation Home Deals in Siesta Key

Save up to 73%

Condo Siesta Key
Oct 19 - Oct 26
-73%
$381
$103
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family Friendly Beautiful Condo in Siesta Key with Screened-In Balcony

4.7
Excellent (77 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Jan 4 - Jan 11
-53%
$993
$464
per night
House ∙ 11 guests ∙ 5 bedrooms

House in Siesta Key with Pool, Yard & Grill + Beach Views

4.6
Excellent (11 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Apartment Siesta Key
May 10 - May 17
-41%
$220
$129
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Lovely Rental Apartment in Siesta Key

4.5
Excellent (33 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Choose among 7,232 offers available in Siesta Key and discover a wonderful spot for your vacation. Using HomeToGo you can directly compare the offers of each listed rental to discover the best price and save up to 72%.

Recommended Vacation Rentals in Siesta Key

Find your perfect vacation rental in Siesta Key: from $81 per night

Condo Siesta Key
Nov 2 - Nov 9
$273
per night
Condo ∙ 8 guests ∙ 2 bedrooms

Condo in Siesta Key

Siesta Key, Sarasota County, Florida, United States
View deal
Cottage Siesta Key
Sep 23 - Sep 30
-79%
$600
$128
per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Cottage in Siesta Key

4.5
Excellent (188 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Sep 21 - Sep 28
$150
per night
House ∙ 4 guests ∙ 2 bedrooms

Nice Vacation Home in Siesta Key with Patio + Beach Nearby

4.9
Outstanding (62 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Nov 1 - Nov 8
-68%
$1,700
$543
per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Bay Isle

4.5
Excellent (2 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
Dec 7 - Dec 14
$156
per night
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home in Sarasota with Free Parking

5.0
Outstanding (45 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Sep 21 - Sep 28
-74%
$951
$248
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Siesta Key with Private Balcony + Beach View

5.0
Outstanding (8 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Sep 26 - Oct 3
-65%
$524
$185
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Lovely Condo in Siesta Key with Pool, Patio & Grill + Beach Nearby

4.5
Excellent (64 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Sep 6 - Sep 13
-67%
$1,500
$500
per night
House ∙ 12 guests ∙ 5 bedrooms

House in Siesta Key with Spacious Patio

5.0
Outstanding (2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Jul 12 - Jul 19
$111
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Ridge Wood Heights with Yard & Patio

5.0
Outstanding (2 ratings)
Siesta Key, Sarasota County, Florida, United States
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Budget-friendly Vacation Rentals in Siesta Key

Find Fantastic yet Inexpensive Offers

House Siesta Key
Nov 7 - Nov 14
-38%
$800
$500
per night
House ∙ 10 guests ∙ 4 bedrooms

House in Siesta Key with Tropical Garden

4.8
Outstanding (22 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Sep 21 - Sep 28
-45%
$785
$428
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Siesta Key with Spacious Patio

5.0
Outstanding (176 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Dec 14 - Dec 21
-61%
$434
$169
per night
Condo ∙ 7 guests ∙ 2 bedrooms

Beautiful Condo in Siesta Key with Patio & Pool, Queen Size-Bed + Next to Beach

4.1
Very good (36 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Top-Rated Rentals and Accommodations in Siesta Key

Book Vacation Rental Offers with the Highest User Rating

House Siesta Key
Feb 1 - Feb 8
-39%
$1,396
$850
per night
House ∙ 16 guests ∙ 6 bedrooms

House in Siesta Key with Grill & Patio + Spectacular Views + Close to Beach

4.7
Excellent (12 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Sep 23 - Sep 30
$122
per night
House ∙ 8 guests ∙ 3 bedrooms

House in Sarasota with Grill, Pool & Yard

4.7
Excellent (214 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Sep 21 - Sep 28
-67%
$270
$91
per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo in Siesta Key with Sauna, Pool & Grill

5.0
Outstanding (2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Popular Rental Amenities in Siesta Key

  • Pool (5,562)
  • Pet-friendly (1,485)
  • Balcony/patio (2,024)
  • WiFi (6,865)
  • Air conditioning (6,620)
  • Kitchen (6,795)
  • Washing machine (4,950)
  • TV (6,518)
  • Parking (557)
  • Microwave (5,464)
  • Dishwasher (4,861)
  • No smoking (6,528)

Siesta Key is a great vacation destination if you want a rental with a pool, as 77% of the vacation rentals include one. In addition, properties with pools in Siesta Key cost, on average, $564 a night. Most of the listed accommodations with pools are condo. You can also compare and find a vacation rental offering a pool near the water, which is the case for nearly half of the rentals there.

Price and Availability Index in Siesta Key

Click on any bar to see price and availability information

Vacation Rental Price Information in Siesta Key

We analyzed price data and input them into this graph, which shows vacation rental prices for the next year in Siesta Key. It is during a week of February (2/15 – 2/22) that you will find the highest prices for the next 12 months. The lowest average nightly prices can be found in September (9/21 – 9/28).

Rental availability information in Siesta Key

The graph displays the weekly availability rate in Siesta Key for the upcoming year. The week with the lowest percentage of available accommodations is in August (8/23 – 8/30). On the other hand, the week with the most available offers is in September (9/28 – 10/5).

Siesta Key: A Tropical Paradise on Florida's Gulf Coast

Siesta Key has earned its reputation as a premier vacation spot for its stunning natural beauty and laid-back atmosphere. This barrier island off the coast of Sarasota, Florida, is renowned for its pristine white sand beaches, often ranked among the best in the world. The sand, composed of 99% pure quartz, remains cool even on hot days, making it perfect for barefoot walks. Beyond the beach, Siesta Key boasts a vibrant village atmosphere with unique shops, diverse dining options and a relaxed nightlife scene. The island's small size and pedestrian-friendly layout make it easy to explore, while its proximity to Sarasota provides access to additional cultural attractions and amenities. Beyond the beaches, Siesta Key offers a variety of vacation rentals, activities, including water sports, fishing and vibrant nightlife. Its charming village area features eclectic shops, restaurants and live music, making it a well-rounded destination for all types of travelers.

Top 6 Attractions and Where They Are

  1. Siesta Beach (948 Beach Road): The island's most famous beach, known for its wide expanse of white sand and clear waters, perfect for swimming and sunbathing.

  2. Siesta Key Village (Ocean Boulevard): A charming area filled with shops, restaurants and live music venues.

  3. Point of Rocks (southern end of Crescent Beach): A popular spot for snorkeling and observing marine life among limestone formations.

  4. Turtle Beach (8918 Midnight Pass Road): A quieter beach on the southern end of the island, ideal for picnicking, shell collecting and kayaking.

  5. Siesta Key Drum Circle (Siesta Beach): A popular Sunday evening event featuring drumming, dancing and sunset views.

  6. Crescent Beach (situated between Siesta Beach and Turtle Beach): A more secluded atmosphere and access to Point of Rocks for snorkeling enthusiasts.

Best Time to Visit Siesta Key

The ideal time to visit Siesta Key depends on personal preferences and planned activities. Spring (March to May) offers warm temperatures and lower humidity, perfect for beach activities and outdoor exploration. However, this period can be crowded with spring break visitors. Summer (June to August) is the peak tourist season, with hot temperatures ideal for water activities but also bringing larger crowds and higher prices. Fall (September to November) sees fewer tourists and pleasant temperatures, making it an excellent time for a more relaxed visit. Winter (December to February) offers mild temperatures and the lowest prices of the year, though water activities may be limited due to cooler Gulf temperatures. For a balance of good weather, manageable crowds and reasonable prices, consider visiting in late spring or early fall. Keep in mind that hurricane season runs from June to November, with the highest risk typically in August and September.

Best Neighborhoods for Vacation Rentals

Siesta Key offers various areas suitable for vacation rentals, each with its own unique appeal:

  1. Siesta Key Village: Ideal for those who want to be close to dining, shopping and nightlife.

  2. Crescent Beach: A quieter area with beautiful beaches and easy access to Point of Rocks for snorkeling.

  3. Turtle Beach: Perfect for those seeking a more secluded and natural setting.

  4. Gulf and Bay Club: A resort-style community with amenities and beach access.

  5. Sarasota (mainland): Offers proximity to Siesta Key while providing access to additional attractions and services.

  6. Mid-Key Area (located between Siesta Beach and Turtle Beach): This area offers a balanced mix of tranquility and convenience.

Popular Types of Vacation Rentals in Siesta Key

Siesta Key's vacation rental market caters to diverse preferences and group sizes:

  1. Beachfront condos: Offer stunning Gulf views and easy beach access, ideal for couples and small families.

  2. Beach houses: Spacious options ideal for larger families or groups, some with private pools.

  3. Bungalows: Smaller, charming properties that provide a cozy and intimate setting, suitable for couples or solo travelers looking for a unique stay.

  4. Vacation Homes: From quaint cabins to luxurious houses, these rentals provide ample space and a home-like feel, perfect for larger families or groups.

  5. Villas: High-end properties that often include private pools, spacious living areas and premium furnishings, ideal for those seeking a luxury vacation.

These varied rental options ensure that visitors can find accommodations that suit their needs, whether they're seeking a romantic beachfront getaway, a family-friendly house with a pool, or a centrally located apartment for exploring all that Siesta Key has to offer.

Information about vacation rentals in Siesta Key

🏡 Vacation rentals available 7,095 rentals
💳 Possible discounts up to 61%
🌙 Nightly prices starting at $81
⭐ Popular amenities Pool, Pets allowed and Balcony/Patio
🐾 Pet friendly homes 1,440 homes
🏊 Vacation rentals with pools 5,489 homes
13 reviews
Siesta Key vacation rentals have an average rating of 4.8/5 on 13 reviews left by travelers.

Frequently Asked Questions

What is the average price per night for a vacation home in Siesta Key?

The average accommodation in Siesta Key is priced at $81 per night. Average prices for condos are $419 per night. House rentals in Siesta Key cost $756 per night on average.

How many vacation rentals are available to book in Siesta Key?

Currently there are 7,095 rentals to choose from for your upcoming trip.

What amenities are most popular for vacation homes in Siesta Key?

If you're looking to book a vacation rental in Siesta Key, the most common amenities are: Pets allowed, Pool and Balcony/Patio.

How many vacation homes with pools are there in Siesta Key?

There are 5,489 vacation homes from 31 providers in Siesta Key.

Are dogs allowed in vacation rentals in Siesta Key?

If traveling with a dog in Siesta Key, 20% of rentals are pet-friendly.

What's the best time to travel to Siesta Key?

Siesta Key has its warmest time of year in August and June, with average nightly prices around $81.

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