Siesta Key Vacation Rentals - HolidayHomes base64Hash Siesta Key Vacation Rentals - HolidayHomes

Siesta Key Vacation Rentals

Browse 8,092 available vacation homes and compared across 31 trusted partners

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Top-Rated Vacation rentals in Siesta Key

Book the highest-rated Siesta Key vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Condo Siesta Key
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
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House Siesta Key
House with terrace, yard & private pool
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House Siesta Key
Vacation home with hot tub, private pool & grill | Nature view
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Condo Siesta Key
Pleasant condo with barbeque & pool | Nature view | Close to the beach
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House Siesta Key
Fully equipped big vacation home with garden, jacuzzi & private pool | Close to the beach | Suitable for remote work
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Condo Siesta Key
Anchorage Resort 7th Floor 2-Bedroom Condo w Private Balcony Beach Access
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Villa Siesta Key
Newly renovated. Gulf-side condo. Your own private beach directly on Siesta Key.
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House Siesta Key
Beautiful 5 Bedroom Home Directly on Siesta Key Beach!
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Condo Siesta Key
Condo with heated pool & terrace
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Condo Siesta Key
Buttonwood 432 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
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House Siesta Key
Beach Access, Pools, Tennis and Pickleball - 1225 Gulf & Bayside
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House Siesta Key
Bright and Beachy 5 Bedroom/3 Bath House. Short Walk to Beach & SK Village!
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Condo Siesta Key
Spacious Beachfront Condo on Lido Beach in Sarasota
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House Siesta Key
House with private pool & barbecue
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Condo Siesta Key
Buttonwood 467 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
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Top 15 most Recommended Vacation Rentals in Siesta Key

Discover your ideal Siesta Key vacation rental with real-time comparisons of 8,092 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Siesta Key
Condo ∙ 6 guests ∙ 2 bedrooms

126 m² Condo

Siesta Key, Sarasota County, Florida, United States
This spacious 6-person condo in Sarasota features a heated pool and offers a perfect retreat for families and events.
from $144
per night
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House Siesta Key
House ∙ 4 guests ∙ 2 bedrooms

128 m² House

Siesta Key, Sarasota County, Florida, United States
Charming house rental in Sarasota for 4 guests with a fully equipped kitchen and pet-friendly accommodations.
from $109
per night
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House Siesta Key
House ∙ 6 guests ∙ 3 bedrooms

185 m² House

Siesta Key, Sarasota County, Florida, United States
This house rental in Southgate accommodates 6 guests and features a family-friendly kitchen and a spacious yard for outdoor activities.
from $281
per night
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Condo Siesta Key
Condo ∙ 6 guests ∙ 2 bedrooms

111 m² Condo

Siesta Key, Sarasota County, Florida, United States
This spacious 6-person condo in Siesta Key features a modern kitchen and access to a beautiful pool.
from $253
per night
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Villa Siesta Key
4 guests ∙ 1 bedroom

Villa

Siesta Key, Sarasota County, Florida, United States
This charming villa in Siesta Key accommodates 4 guests and features beach access for a perfect coastal getaway.
from $278
per night
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House Siesta Key
House ∙ 4 guests ∙ 1 bedroom

62 m² House

Siesta Key, Sarasota County, Florida, United States
This house rental in Siesta Key accommodates 4 guests and features a private pool for relaxation and fun.
from $279
per night
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House Siesta Key
4 guests ∙ 2 bedrooms

House

Siesta Key, Sarasota County, Florida, United States
This cozy house rental in Siesta Key accommodates 4 guests and features a private pool for relaxation and fun.
from $401
per night
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House Siesta Key
House ∙ 16 guests ∙ 6 bedrooms

557 m² House

Siesta Key, Sarasota County, Florida, United States
This spacious house rental in Lido Key accommodates 16 guests and features a private pool for a perfect getaway.
from $1,105
per night
(41)
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Condo Siesta Key
Condo ∙ 6 guests ∙ 2 bedrooms

116 m² Condo

Siesta Key, Sarasota County, Florida, United States
This spacious 6-person condo in Siesta Key features a beautiful balcony with stunning sea views.
from $229
per night
(71)
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