Siesta Key Vacation Rentals - Wimdu base64Hash Siesta Key Vacation Rentals - Wimdu

Siesta Key Vacation Rentals

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Choose from 8,030 vacation rentals and homes for your trip!

Best-rated vacation rentals in Siesta Key

Discover vacation rentals with top-notch guest ratings

House Siesta Key
from $526 per night
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented spacious house with jacuzzi, yard & BBQ | Close to the beach | Perfect for remote work

5.0
Outstanding(163 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $262 per night
House ∙ 28 guests ∙ 8 bedrooms

House with terrace, yard & private pool

4.9
Outstanding(151 ratings)
Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
from $228 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with hot tub, private pool & grill

5.0
Outstanding(79 ratings)
Siesta Key, Sarasota County, Florida, United States
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Pet-friendly rentals in Siesta Key

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House Siesta Key
from $221 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with barbeque & private pool | Good for workation | Pets allowed

5.0
Outstanding(2 ratings)
Siesta Key, Sarasota County, Florida, United States
Pet-friendly
View deal
House Siesta Key
from $303 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with garden, patio & barbecue | Nature view

4.7
Excellent(29 ratings)
Siesta Key, Sarasota County, Florida, United States
Pet-friendly
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House Siesta Key
from $336 per night
House ∙ 8 guests ∙ 3 bedrooms

House with terrace, barbeque & private pool | Suitable for remote work

5.0
Outstanding(105 ratings)
Siesta Key, Sarasota County, Florida, United States
Pet-friendly
View deal
See all pet-friendly offers

Vacation rentals with pool in Siesta Key

Discover best cabin and house rentals with pool in Siesta Key

Condo Siesta Key
from $410 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Family-oriented charming condo with private pool & barbeque | Beach nearby

5.0
Outstanding(7 ratings)
Siesta Key, Sarasota County, Florida, United States
Pool
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House Siesta Key
from $234 per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with heated pool & barbeque | Nature view | Suitable for remote work

4.7
Excellent(22 ratings)
Siesta Key, Sarasota County, Florida, United States
Pool
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House Siesta Key
from $936 per night
House ∙ 8 guests ∙ 4 bedrooms

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

5.0
Outstanding(33 ratings)
Siesta Key, Sarasota County, Florida, United States
Pool
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See all offers with pool

Best vacation rental offers in Siesta Key

Condo Siesta Key
from $219 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo with barbecue & pool

5.0
Outstanding(2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $275 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-friendly condo with heated pool, grill & terrace | Water view | Beach nearby

4.7
Excellent(41 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $599 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with barbecue & patio

4.7
Excellent(40 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $392 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with heated pool, patio & barbeque

5.0
Outstanding(129 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $913 per night
House ∙ 8 guests ∙ 4 bedrooms

House with private pool & barbecue

5.0
Outstanding(13 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $476 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Child-friendly wonderful condo with barbeque, private pool & jacuzzi | Beach nearby

4.9
Outstanding(78 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $391 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Child-friendly condo with private pool & BBQ | Beach nearby

4.7
Excellent(21 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Villa Siesta Key
from $354 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa with garden, barbecue & pool | Suitable for remote work

Siesta Key, Sarasota County, Florida, United States
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House Siesta Key
from $295 per night
House ∙ 16 guests ∙ 5 bedrooms

Family-friendly wonderful house with private pool, terrace & hot tub | Next to the beach | Pets allowed

5.0
Outstanding(1 rating)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $563 per night
Condo ∙ 6 guests ∙ 3 bedrooms

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

4.9
Outstanding(44 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $513 per night
House ∙ 10 guests ∙ 4 bedrooms

House with terrace, barbeque & pool | Beach nearby | Pets are welcome

Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $295 per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with grill & heated pool

4.6
Excellent(5 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $383 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with garden, private pool & patio

4.8
Outstanding(38 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $179 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with sauna, heated pool & barbecue | City view | Perfect for remote work

4.7
Excellent(42 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $234 per night
House ∙ 8 guests ∙ 3 bedrooms

House with heated pool, grill & hot tub | Nature view | Perfect for remote work

5.0
Outstanding(2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $307 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with grill, private pool & yard | City view | Suitable for remote work

5.0
Outstanding(54 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $226 per night
House ∙ 8 guests ∙ 3 bedrooms

House with yard, barbeque & private pool | Nature view

4.8
Outstanding(53 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $130 per night
House ∙ 6 guests ∙ 3 bedrooms

House with BBQ, terrace & hot tub | Perfect for remote work

4.8
Outstanding(9 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $604 per night
House ∙ 8 guests ∙ 3 bedrooms

House with pool

5.0
Outstanding(2 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $264 per night
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented house with BBQ, jacuzzi & private pool | Suitable for remote work

5.0
Outstanding(50 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $331 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with private pool

4.8
Outstanding(69 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $178 per night
Condo ∙ 3 guests ∙ 1 bedroom

Condo with patio | City view

5.0
Outstanding(232 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $187 per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly vacation home with yard, patio & barbeque | City view | Suitable for remote work

4.9
Outstanding(12 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $523 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped vacation home with barbeque & pool | Close to the beach

5.0
Outstanding(5 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $269 per night
House ∙ 10 guests ∙ 4 bedrooms

Children-friendly vacation home with private pool, terrace & jacuzzi | Suitable for remote work

5.0
Outstanding(48 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $301 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped pleasant condo with pool & terrace | Beach nearby | Perfect for remote work

5.0
Outstanding(16 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $173 per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with sauna, heated pool & barbeque | City view

4.9
Outstanding(43 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $203 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented house with garden, terrace & private pool | Nature view

5.0
Outstanding(99 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
House Siesta Key
from $259 per night
House ∙ 7 guests ∙ 4 bedrooms

Vacation home with patio, hot tub & private pool

4.9
Outstanding(44 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Condo Siesta Key
from $179 per night
Condo ∙ 4 guests ∙ 1 bedroom

Fully equipped condo with barbecue, sauna & terrace | Beach nearby | Good for workation

5.0
Outstanding(4 ratings)
Siesta Key, Sarasota County, Florida, United States
View deal
Show all 5668 apartments in Siesta Key

Price and Availability Index in Siesta Key

Click on any bar to see price and availability information

Vacation Rental Price Information in Siesta Key

Check the graph above to find out what's the best time to travel and find accommodation in Siesta Key. The most expensive month is March, with an average accommodation price of $826. However, there are periods when prices drop significantly. Booking accommodation for your trip is most affordable in September. In the period 9/12 – 9/19, you will pay on average $559 per night.

Rental availability information in Siesta Key

This graph displays the availability of vacation rentals in Siesta Key over the next 12 months. Only 22% of the vacation rentals in Siesta Key are available in July. If you'd like to visit then, make sure to book early! In contrast, the month with the highest availability rate in Siesta Key is September.

370 reviews
370 travelers who stayed in Siesta Key rated their vacation home 4.6/5 stars on average.

And we love our apartments

Condo with barbecue & pool
Family-friendly condo with heated pool, grill & terrace | Water view | Beach nearby
Vacation home with barbecue & patio
Condo with heated pool, patio & barbeque
House with private pool & barbecue
Show all 5668 apartments in Siesta Key

Features of Siesta Key vacation rentals

💳 Discounts up to 43%
⭐ Popular amenities Air conditioning, Pool and Internet
🏊  Vacation rentals with a pool 5,797 rentals
🌙 Minimum price starting at $137
🐾 Pet friendly vacation homes 1,690 rentals
🏡 Rentals available 8,030 rentals

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