Vacation rentals in Siesta Key - HomeToGo base64Hash Vacation rentals in Siesta Key - HomeToGo

Vacation rentals in Siesta Key

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Top 15 Recommended vacation rentals in Siesta Key

Find your perfect vacation rental in Siesta Key from just $123 per night!

House Siesta Key
-57%
Sep 6 - Sep 13
Free cancellation
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with BBQ

Siesta Key, Sarasota County, Florida, United States
$1,616$691
per night
$1,616$691
per night
View deal
Villa Siesta Key
Sep 6 - Sep 13
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with BBQ, heated pool & patio

Siesta Key, Sarasota County, Florida, United States
$321
per night
Outstanding(7 ratings)
$321
per night
View deal
Condo Siesta Key
Jul 26 - Aug 2
Condo ∙ 8 guests ∙ 4 bedrooms

Child-friendly condo with heated pool, sauna & grill | Nature view | Close to the beach

Siesta Key, Sarasota County, Florida, United States
$396
per night
Outstanding(45 ratings)
$396
per night
View deal
House Siesta Key
-64%
Sep 23 - Sep 30
House ∙ 9 guests ∙ 4 bedrooms

Fully equipped vacation home with heated pool, terrace & grill | Nature view | Beach nearby

Siesta Key, Sarasota County, Florida, United States
$1,075$389
per night
Excellent(56 ratings)
$1,075$389
per night
View deal
House Siesta Key
-29%
Aug 16 - Aug 23
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped vacation home with yard, BBQ & heated pool | Nature view | Next to the beach

Siesta Key, Sarasota County, Florida, United States
$886$625
per night
Outstanding(30 ratings)
$886$625
per night
View deal
House Siesta Key
-63%
Sep 6 - Sep 13
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with yard, BBQ & private pool | City view

Siesta Key, Sarasota County, Florida, United States
$484$178
per night
Outstanding(41 ratings)
$484$178
per night
View deal
House Siesta Key
-28%
Sep 13 - Sep 20
House ∙ 8 guests ∙ 4 bedrooms

House with terrace & barbecue | Nature view

Siesta Key, Sarasota County, Florida, United States
$900$650
per night
Outstanding(39 ratings)
$900$650
per night
View deal
House Siesta Key
-55%
Sep 20 - Sep 27
House ∙ 11 guests ∙ 5 bedrooms

Vacation home with private pool, grill & patio | Nature view

Siesta Key, Sarasota County, Florida, United States
$957$428
per night
Excellent(109 ratings)
$957$428
per night
View deal
House Siesta Key
-16%
Apr 26 - May 3
House ∙ 6 guests ∙ 2 bedrooms

Children-friendly lovely vacation home with barbeque | Next to the beach

Siesta Key, Sarasota County, Florida, United States
$457$385
per night
Excellent
$457$385
per night
View deal
House Siesta Key
-51%
Sep 20 - Sep 27
House ∙ 9 guests ∙ 3 bedrooms

Vacation home with pool & barbeque

Siesta Key, Sarasota County, Florida, United States
$533$263
per night
Outstanding
$533$263
per night
View deal
House Siesta Key
-57%
Aug 1 - Aug 8
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with private pool, yard & barbeque | Suitable for remote work

Siesta Key, Sarasota County, Florida, United States
$1,000$428
per night
Outstanding(125 ratings)
$1,000$428
per night
View deal
House Siesta Key
-81%
Sep 26 - Oct 3
Free cancellation
House ∙ 10 guests ∙ 4 bedrooms

Children-friendly house with private pool & grill | Water view | Beach nearby | Perfect for remote work

Siesta Key, Sarasota County, Florida, United States
$2,323$437
per night
Outstanding(93 ratings)
$2,323$437
per night
View deal
Condo Siesta Key
-54%
May 17 - May 24
Condo ∙ 6 guests ∙ 3 bedrooms

Family-oriented lovely condo with sauna, yard & heated pool | Next to the beach

Siesta Key, Sarasota County, Florida, United States
$500$228
per night
Outstanding(58 ratings)
$500$228
per night
View deal
Condo Siesta Key
Aug 2 - Aug 9
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with heated pool & barbeque | Nature view

Siesta Key, Sarasota County, Florida, United States
$525
per night
Outstanding(5 ratings)
$525
per night
View deal
Condo Siesta Key
-61%
Sep 6 - Sep 13
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with heated pool, barbecue & patio | City view | Next to the beach

Siesta Key, Sarasota County, Florida, United States
$823$319
per night
Outstanding(85 ratings)
$823$319
per night
View deal

Vacation rentals and apartments with air conditioning

House  Siesta Key
Sep 13 - Sep 20
-59%
$757
$311
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with grill

Siesta Key, Sarasota County, Florida, United States
Free cancellation
Air conditioning
View deal
Condo  Siesta Key
Jul 19 - Jul 26
-48%
$335
$175
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with heated pool, barbecue & yard | Nature view

5.0
Outstanding(2 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
House  Siesta Key
Sep 6 - Sep 13
-81%
$1,298
$241
per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped lovely vacation home with private pool & BBQ | City view | Next to the beach | Dogs allowed

4.9
Outstanding(28 ratings)
Siesta Key, Sarasota County, Florida, United States
Air conditioning
View deal
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Vacation houses with Balconies or Patios

Condo  Siesta Key
Aug 9 - Aug 16
-32%
$374
$256
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with heated pool, BBQ & terrace

4.8
Outstanding(20 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
House  Siesta Key
May 11 - May 18
-70%
$1,421
$432
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with terrace, heated pool & grill | City view | Perfect for remote work

4.0
Very good(1 rating)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
House  Siesta Key
Aug 2 - Aug 9
-66%
$620
$214
per night
House ∙ 10 guests ∙ 3 bedrooms

Fully equipped house with garden, private pool & BBQ | Nature view | Pet-friendly

4.8
Outstanding(19 ratings)
Siesta Key, Sarasota County, Florida, United States
Balcony/Patio
View deal
See all offers

Vacation homes and rentals with a yard

House  Siesta Key
May 9 - May 16
-50%
$499
$252
per night
House ∙ 11 guests ∙ 4 bedrooms

Fully equipped house with yard, barbeque & private pool | Perfect for remote work | Pets allowed

Siesta Key, Sarasota County, Florida, United States
Yard
View deal
House  Siesta Key
Oct 11 - Oct 18
$695
per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, garden & barbecue

5.0
Outstanding(10 ratings)
Siesta Key, Sarasota County, Florida, United States
Yard
View deal
House  Siesta Key
Jul 5 - Jul 12
$344
per night
House ∙ 28 guests ∙ 8 bedrooms

House with terrace, yard & private pool

4.9
Outstanding(149 ratings)
Siesta Key, Sarasota County, Florida, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Siesta Key

Save up to 45%

Condo Siesta Key
Sep 6 - Sep 13
-40%
$425
$256
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with heated pool & BBQ

5.0
Outstanding(10 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Sep 13 - Sep 20
-34%
$368
$243
per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped charming house with private pool | Nature view | Suitable for remote work | Pets are welcome

5.0
Outstanding(2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
Aug 23 - Aug 30
-45%
$785
$428
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with terrace & barbeque | Nature view

5.0
Outstanding(175 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Choose among 9,081 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 67%.

Budget-friendly Vacation Rentals in Siesta Key

Find Fantastic yet Inexpensive Offers

Condo Siesta Key
Apr 25 - May 2
$141
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped nice condo with grill & heated pool | Nature view | Beach nearby

5.0
Outstanding(12 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
May 28 - Jun 4
-34%
$211
$139
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with pool & jacuzzi | Perfect for remote work

3.0
(13 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Aug 9 - Aug 16
-62%
$713
$270
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped charming condo with barbecue & pool | Beach nearby

4.7
Excellent(6 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

Condo Siesta Key
Sep 13 - Sep 20
-55%
$475
$215
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with BBQ, heated pool & garden

4.7
Excellent(11 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Oct 11 - Oct 18
-22%
$325
$254
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Ample condo with barbeque & heated pool | Nature view | Close to the beach

5.0
Outstanding(9 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
Sep 20 - Sep 27
-49%
$432
$219
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with sauna, BBQ & pool

5.0
Outstanding(4 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal

Customer ratings and reviews

How are reviews collected?
ANDREW T.
Guest verified by HomeToGo

The condo location is excellent! The amenities of the condo association (pool, tennis, and pickleball courts, and secure parking), were excellent, the condo unit itself was a bit dated, but clean and well appointed. WiFI was fast and tv offerings from Netflix, Prime Video, Hulu, Paramount , were nice to be able to watch in the evening after a day at the beach or lounging at the pool.

Reviewed on 4/1/2025 | Family
Condo Siesta Key
from $213
per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.5
Excellent(58 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Vanessa Y.
Guest verified by HomeToGo

We enjoyed our stay at Avanti Villa 534. The property is exactly like the pictures and was clean. Not a bad walk to the beach or village. We incurred no problems with any features of the property and communication was great with the host. They even left a delicious treat on arrival, and some nice starter necessities such as cleaning and bathing products! They also offered us another nights stay, but unfortunately we couldn’t take advantage of it ! We had a wonderful stay, just wish it could have been longer! One thing I will say, and it has nothing to do with the property, but bring bug spray when you come, the no-see-ums are brutal!

Reviewed on 7/2/2024 | Family
House Siesta Key
from $347
per night
HomeToGo
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Michael G.
Guest verified by HomeToGo

Home was very nice and was as represented. Service was responsive and excellent.

Reviewed on 7/2/2024 | Family
House Siesta Key
from $739
per night
HomeToGo
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(49 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Pete M.
Guest verified by HomeToGo

Just a few things missing: facial tissues, hand soap in bathrooms, bed pillows that were too high to be comfortable. The towels provided by service were sometimes gross, sometimes ok, Most frustrating was the tv in living room. Only being able to watch on Youtube tv made us miss several of our morning news shows. Had to watch the NFL Sunday night game outside by the pool, bundled in blankets. Overall, very good vacationtime there. Too bad the weather was so cold.

Reviewed on 1/29/2024 | Couple
House Siesta Key
from $507
per night
HomeToGo
House ∙ 12 guests ∙ 3 bedrooms
5.0
Outstanding(43 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Amy S.
Guest verified by HomeToGo

Endless Views was a perfect spot for our vacation to Siesta Key. Roomy, clean, and with the added plus on an elevator for our luggage and handicapped son. A short walk to both the village and the beach. We enjoyed every minute!

Reviewed on 3/13/2023 | Family
House Siesta Key
from $355
per night
HomeToGo
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(21 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Siesta Key

  • Pool (6,179)
  • Pet-friendly (1,711)
  • Balcony/patio (2,140)
  • WiFi (8,377)
  • Air conditioning (7,998)
  • Kitchen (8,311)
  • Washing machine (5,348)
  • TV (7,756)
  • Parking (663)
  • Microwave (6,563)
  • Dishwasher (4,861)
  • No smoking (7,859)

Siesta Key is a great vacation destination if you want a rental with a pool, as 68% of the vacation rentals include one. In addition, properties with pools in Siesta Key cost, on average, $599 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 one-third 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 December (12/27 – 1/3) that you will find the highest prices for the next 12 months. The lowest average nightly prices can be found in September (9/13 – 9/20).

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 April (4/4 – 4/11). On the other hand, the week with the most available offers is in November (11/1 – 11/8).

What are the best activities for families in Siesta Key?

Siesta Key with Kids

Got kids? After a morning sleeping in at your Siesta Key vacation home, go check out the Crowley Museum & Nature Center, 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 vacation rental is the Florida Gulf Coast Railroad Museum, open most weekends. At the Mote Marine Laboratory and Science Center, 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 vacation activities around Siesta Key Beach, you’ll have a great time. Your Siesta Key vacation home has all the amenities you need to make this vacation perfect.

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

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 9,081 rentals
💳 Possible discounts up to 67%
🌙 Nightly prices starting at $123
⭐ Popular amenities Pool, Pets allowed and Balcony/Patio
🐾 Pet friendly homes 1,718 homes
🏊 Vacation rentals with pools 6,192 homes
108,224 reviews
Siesta Key vacation rentals have an average rating of 4.6/5 on 108,224 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 $123 per night. Average prices for condos are $426 per night. House rentals in Siesta Key cost $745 per night on average.

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

Currently there are 9,081 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 6,192 vacation homes from 29 providers in Siesta Key.

Are dogs allowed in vacation rentals in Siesta Key?

If traveling with a dog in Siesta Key, 19% 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 $123.

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