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Siesta Key Vacation Rentals

Find 6,265 available offers from 33 partners
Siesta Key
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Siesta Key
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Siesta Key vacation rentals: the perfect beach holiday in an island paradise

Not far from Sarasota, and just next to the enticing Gulf of Mexico, sits the eight mile long Siesta Key. It’s been named America’s Best Beach, and once you get here, it’s easy to see why. Its four main beaches are best known for their white sand, pure blue waters, and lots of sports activities.

A family-friendly location, the region is ideal for those with children, however Siesta Key also offers the perfect romantic setting for couples. Dinner while bathed in moonlight at a waterfront oyster bar? Breakfast from your beach terrace in your Siesta Key holiday home? With any Siesta Key holiday letting you choose, you’ll have direct access to the bay and beach — just footsteps away. Around the shore are many dining options and plenty of activities to choose from. Restaurants range from budget to luxurious; the beaches here some of the most coveted in the country. In short, Siesta Key is an island paradise.

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Holiday lettings and apartments with air conditioning

Good weather while on holiday is always great - and it's a plus to be able to control the temperature in your accommodation too. Find holiday homes and apartments in Siesta Key with air conditioning and cooling systems to ensure maximum comfort during your stay.

House  Siesta Key
21 Sept - 28 Sept
£267 per night
House ∙ 4 guests ∙ 2 bedrooms

Beautiful House in Siesta Key

4.5
Excellent (48 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
Details
Vrbo
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Condo  Siesta Key
21 Sept - 28 Sept
£470 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Pleasant Flat in Siesta Key with Pool & Barbecue

4.9
Outstanding (10 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Condo  Siesta Key
21 Sept - 28 Sept
£234 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Flat in Siesta Key with Pool, Terrace & Barbecue

5.0
Outstanding (1 rating)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
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Best holiday homes with a patio or terrace

Want to admire Siesta Key's vistas from the comfort of a holiday apartment, or enjoy private outside space while staying in a Siesta Key holiday home? Take a look at our top lettings with balconies and patios in Siesta Key and find the perfect accommodation for your stay.

Villa  Siesta Key
27 Apr - 4 May
-32%
£527
£361 per night
Villa ∙ 10 guests ∙ 3 bedrooms

Villa in Siesta Key with 2-Car Garage

5.0
Outstanding (1 rating)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
Details
HomeToGo
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House  Siesta Key
21 Sept - 28 Sept
£409 per night
House ∙ 11 guests ∙ 4 bedrooms

Holiday Home in Siesta Key with Barbecue & Pool

4.7
Excellent (100 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
Details
Vrbo
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Condo  Siesta Key
21 Sept - 28 Sept
£200 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Flat in Sarasota with Pool & Barbecue + Beach Nearby

4.7
Excellent (91 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
Details
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Holiday rentals with wifi

Whether it's for working remotely or streaming your favourite shows, internet access can be an indispensable amenity when it comes to choosing a holiday home. Check out HomeToGo's range of holiday lettings with WiFi in Siesta Key and enjoy a fast and reliable internet connection during your stay.

Condo  Siesta Key
21 Sept - 28 Sept
-19%
£601
£486 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Spacious Flat in Sarasota with Barbecue, Pool & Terrace + Beach Views

4.6
Excellent (64 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
Details
Vrbo
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Condo  Siesta Key
21 Sept - 28 Sept
£234 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Flat in Siesta Key with Sauna, Pool & Barbecue

Siesta Key, Sarasota County, Florida, United States
Internet
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Condo  Siesta Key
11 May - 18 May
£205 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family Friendly Flat in Siesta Key with Open Balcony

5.0
Outstanding (136 ratings)
Siesta Key, Sarasota County, Florida, United States
Internet
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Best holiday rental deals in Siesta Key

Save up to 16%

House Siesta Key
22 Sept - 29 Sept
-4%
£381
£367 per night
House ∙ 6 guests ∙ 4 bedrooms

Holiday Home in Sarasota with Free Parking

5.0
Outstanding (31 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Condo Siesta Key
21 Sept - 28 Sept
-16%
£362
£305 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Flat in Sarasota with Private Balcony

5.0
Outstanding (125 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Condo Siesta Key
21 Sept - 28 Sept
-6%
£212
£199 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Flat in Sarasota with Pool & Barbecue

4.8
Outstanding (13 ratings)
Siesta Key, Sarasota County, Florida, United States
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Easily find the perfect holiday letting from £140 per night by searching and comparing the 6,265 options listed in Siesta Key. By comparing these different offers, HomeToGo highlights the lowest prices and the highest rated lettings in Siesta Key.

Recommended holiday lettings in Siesta Key

Rent a holiday home, apartment or cottage in Siesta Key from just £140 per night

Condo Siesta Key
21 Sept - 28 Sept
-7%
£218
£202 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Flat in Siesta Key with Barbecue, Terrace & Pool

4.9
Outstanding (148 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Condo Siesta Key
21 Sept - 28 Sept
£283 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Flat in Siesta Key with Large Pool

5.0
Outstanding (2 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
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House Siesta Key
21 Sept - 28 Sept
£365 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday Home in Bay Isle with Jetted Whirlpool

4.8
Outstanding (55 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
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Condo Siesta Key
6 Oct - 13 Oct
-59%
£439
£180 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Flat in Siesta Key with Gorgeous Pool + Water Views

4.3
Very good (74 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vacasa
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House Siesta Key
26 Jun - 3 Jul
£233 per night
House ∙ 4 guests ∙ 1 bedroom

Charming House in Sarasota with Pool, Terrace & Garden

4.1
Very good (60 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
HomeToGo
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Condo Siesta Key
21 Sept - 28 Sept
£336 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Flat in Siesta Key with Salt-Water Pool + Gulf View

5.0
Outstanding (2 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Condo Siesta Key
14 Sept - 21 Sept
-59%
£510
£209 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Flat in Siesta Key with Pool & Barbecue

4.2
Very good (57 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
HomeToGo
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House Siesta Key
21 Sept - 28 Sept
£524 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday Home in Siesta Key with Spacious Patio

5.0
Outstanding (172 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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House Siesta Key
11 May - 18 May
£422 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Sarasota with Pool, Barbecue & Terrace + Close to Beach

5.0
Outstanding (125 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
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Budget-friendly Holiday Homes in Siesta Key

Find Fantastic yet Cheap Lettings

House Siesta Key
26 Jun - 3 Jul
£441 per night
House ∙ 10 guests ∙ 3 bedrooms

Nice House in Sarasota with Garden, Barbecue & Pool

4.3
Very good (26 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
HomeToGo
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Condo Siesta Key
7 Dec - 14 Dec
-36%
£337
£216 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Nice Flat in Siesta Key with Direct Balcony + Water Views + Next to Beach

4.7
Excellent (27 ratings)
Siesta Key, Sarasota County, Florida, United States
Free cancellation
Details
HomeToGo
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House Siesta Key
21 Sept - 28 Sept
£141 per night
House ∙ 3 guests ∙ 1 bedroom

Beautiful Holiday Home in Siesta Key with Barbecue & Terrace

4.9
Outstanding (76 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Top-Rated Lettings and Properties in Siesta Key

Book Holiday Letting Offers with the Highest User Rating

House Siesta Key
21 Sept - 28 Sept
-35%
£358
£233 per night
House ∙ 4 guests ∙ 2 bedrooms

Rental House in Southgate with Overnight Parking

4.8
Outstanding (55 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Condo Siesta Key
21 Sept - 28 Sept
£207 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Flat in Siesta Key with Pool

4.8
Outstanding (47 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Condo Siesta Key
21 Sept - 28 Sept
£373 per night
Condo ∙ 4 guests ∙ 1 bedroom

Flat in Siesta Key with Open Balcony + Amazing Views

4.7
Excellent (150 ratings)
Siesta Key, Sarasota County, Florida, United States
Details
Vrbo
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Popular holiday rental amenities in Siesta Key

  • Pool (5,025)
  • WiFi (6,124)
  • Air conditioning (5,932)
  • Parking (461)
  • TV (5,750)
  • Washing machine (4,403)
  • Balcony/patio (2,090)
  • Grill (4,523)
  • Dishwasher (4,544)
  • Kitchen (6,017)
  • No smoking (6,010)
  • Microwave (5,053)

Siesta Key is a good holiday spot if you would like to rent a letting with a pool. More than two-thirds of the offers here boast this feature. Additionally, more condo have pools than any other accommodation type. They are an excellent choice if you go in a group of 5, as that is the number of people they can welcome on average. If, ideally, you would like to be close to the water, more than half of the holiday rentals with a pool are located within 2 kilometres of the waterfront.

Price and Availability Index for Siesta Key

Click on any bar to see price and availability information

Holiday Letting Price Information in Siesta Key

This graph displays the average prices for the next twelve months in Siesta Key. Holiday letting prices are the highest in February (15/02 – 22/02). Prices are lower in September (14/09 – 21/09).

Rental availability information in Siesta Key

Our availability graph helps you identify the busiest months in Siesta Key. The week with the highest booking rate in the next 6 months is in February (15/02 – 22/02), when 79% of the holiday lettings are booked. People tend to travel to Siesta Key least during a week in September (14/09 – 21/09) when only 30% of the rentals are booked.

The Weather in Siesta Key

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25°
14°
5 days 5
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23°
13°
6 days 6
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26°
15°
7 days 7
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29°
18°
7 days 7
max.
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31°
20°
8 days 8
max.
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32°
23°
14 days 14
max.
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32°
24°
16 days 16
max.
Min.
33°
24°
18 days 18
max.
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32°
23°
15 days 15
max.
Min.
29°
20°
7 days 7
max.
Min.
26°
16°
6 days 6
max.
Min.
25°
15°
5 days 5
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. During August, maximum temperatures climb above 33°. Conversely, February is the coldest month in Siesta Key, with temperatures falling below 13°. January is the driest month.

7-Day Weather Forecast in Siesta Key

Sat, 13 Apr
25°
23°

0%

6 h

14 km/h

Sun, 14 Apr
26°
23°

0%

6 h

10 km/h

Mon, 15 Apr
27°
25°

0%

3 h

16 km/h

Tue, 16 Apr
27°
26°

0%

2 h

19 km/h

Wed, 17 Apr
28°
26°

0%

1 h

20 km/h

Thu, 18 Apr
28°
26°

0%

1 h

18 km/h

Fri, 19 Apr
29°
27°

0%

1 h

20 km/h

Accommodation options for your holiday in Siesta Key

One-third of the accommodation options (33.17%) in Siesta Key are house rentals. They are the most typical properties there. The average price of house rentals is £517 per night, with an average area of 201 m². Moreover, these holiday rentals are usually a great option for large groups, as that is the average number of guests that house rentals can welcome in Siesta Key. You can also look at other types of accommodation in Siesta Key. For example, apartment rental are another common type of accommodation in Siesta Key, with 365 offers listed. Apartment rental in Siesta Key are 128 m² on average, with an average price of £335 a night.
Where to find the best food in Siesta Key?

What to eat in Siesta Key

Being a beach destination means there’s unlimited seafood to enjoy. When you come to Siesta Key, be sure to try out the well-known seafront restaurants. Try the freshest lobsters, crabs and crayfish; sip margaritas in the sunshine, or twilight. Whether cooking in your Siesta Key holiday letting , or dining out in this relaxed beachy vibe, you’ll enjoy this part of every day.

What is the weather like in Siesta Key?

Perfect beach climate in Siesta Key

Come to your Siesta Key holiday letting during the summer to enjoy Siesta Key’s warm yet temperate climate. May through September are the warmest months of the year, while Siesta Key’s cold season goes from December until February. So if you want to get some sunbathing in, plan to come during the early to mid-summer months.

What are the top sights in Siesta Key?

The beaches of Siesta Key

Water sport lovers will have a blast in Siesta Key; it’s the ultimate beach destination. Its four main areas are: Siesta Beach, Crescent Beach, Turtle Beach and Siesta Key Village. When staying in your Siesta Key holiday letting , try visiting each one, as they all have a unique charm.

The most popular, Siesta Beach, was in fact rated the number one beach in the United States in 2011. Here, you can lounge on its lovely quartz sand, enjoying the cool feeling under your toes. Try some active sports in the tennis and volleyball courts, or go with your family for a picnic. For catching the gorgeous sunset, head to Crescent Beach, known for its fine white sands. With its stunning blue waters and peaceful vibe, it’s also a great place for a romantic date with your favourites person.

You’ll find Turtle Beach on Siesta Key’s southern tip. It's notably darker sand has more shells, so if you love collecting, or have little ones who do, head there. There are also playgrounds and sports areas on the sand, which is likely to be not close to your Siesta Beach holiday letting .

Siesta Village is where you’ll get to see wildlife like parrots and various shore birds. Don’t forget your camera if you enjoy nature photography. You may just spy a beautiful snowy egret, an ibis or a stork. Those who love the underwater thrill of snorkeling can head out to Point of Rocks. It’s an area lauded as the best spot on Florida’s west coast for snorkeling.

What are the best activities for families in Siesta Key?

Where to go with children in Siesta Key

Got kids? After a morning sleeping in at your Siesta Key holiday home, go check out the Crowley Museum & Nature Centre, where you can enjoy hiking around nature trails, visit the wildlife sanctuary, and overlook the Myakka River. Another interesting place for kids near to your Siesta Key holiday letting is the Florida Gulf Coast Railroad Museum, open most weekends. At the Mote Marine Laboratory and Science Centre, both young and old can enjoy learning about marine life. Visit their giant aquariums and see sharks, eels or manatees up close. If your young ones ever want to experience circus life, they can learn all about it at the Circus Museum.

Whether you choose to lounge around on the beach all day, work on your tan, or take up a more active holiday activities around Siesta Key Beach, you’ll have a great time. Your Siesta Key holiday home has all the amenities you need to make this holiday perfect.

What are the must-see attractions in Siesta Key?

Discover paradise at Siesta Key

Point of Rocks

Forming a natural boundary at Crescent Beach's south end, Point-of-Rocks is great for snorkelling and shallow-water bathing. Children will especially enjoy discovering the marine life.

Turtle Beach

Named after the turtles who nest here, Turtle Beach is perfect for family picnics and taking in picturesque sunsets. Collect shells, swim, sunbathe or fish here.

Siesta Farmers Market

This market has it all from fruit, vegetables and olive oil, to paintings, vintage photos, shell artwork, ceramics and beauty products. After bargain hunting, relax with a coffee and enjoy the live music.

Siesta Beach

White-powdered sand, turquoise waters and gentle breezes define the tropical paradise that is Siesta Beach. This award-winning beach is unbeatable for blissful atmosphere, even offering the chance to spot dolphins.

Crescent Beach

This southern portion of Siesta Beach has won the accolade of having "the whitest and finest sand in the world". Paddleboarding, kayaking and snorkelling are popular activities here.

Information about holiday rentals in Siesta Key

🏡 Holiday homes available 6,265 rentals
💳 Discounts available up to 57%
🌙 Nightly prices from £140
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly rentals 944 properties
🏊 Holiday rentals with pools 4,921 properties
10 reviews
Siesta Key holiday rentals have an average rating of 5/5 across 10 reviews left by travellers.

Frequently Asked Questions

How many holiday homes are available to book in Siesta Key?

September is the time of year with the highest amount of House rentals and Apartment rental available in Siesta Key, so you'll find plenty of great holiday deals during this month.

What is the most searched holiday home amenity in Siesta Key?

Travellers planning trips to Siesta Key usually search for Pool, Internet, and Air conditioning as holiday home amenities.

How many holiday lettings with a pool there are on offer in Siesta Key?

Holiday homes with pools are 79 of all in Siesta Key.

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

August and June are the best months for sun lovers in Siesta Key.

Where can I see discounts on holiday accommmodation in Siesta Key?

You can get great value holiday lets in Siesta Key with the nightly price of accommodation beginning at £140 - and HomeToGo has introduced plenty of features that make it a piece of cake to find the best deals. When thinking about the timing for your break, search with HomeToGo's flexible dates technology to quickly locate low-price time periods and get discounts of as much as 57%. In addition, HomeToGo's 'distance from' filter can help you find hidden gem holiday homes in great value, lesser-known spots that are just as close to the area of your choice, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Start searching with time to spare to get the benefits of a wide range of offers and low prices - and do so with confidence by clicking on HomeToGo's 'free cancellation' filter when using the website or app.

What are the pros of booking a holiday home in Siesta Key with HomeToGo?

From serenity away from the crowds to plenty of room for relaxing with your travel companions, holiday lets in Siesta Key offer a wide range of advantages. HomeToGo lets you read genuine ratings from verified visitors, and searching is safe, easy, and stress-free - so with 6,265 lets from 33 providers in the vicinity, you're bound to find the right holiday home with all of the amenities that are important to you in Siesta Key.

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