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

Siesta Key Vacation Rentals

Browse 8,022 available vacation homes and compared across 32 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

House Siesta Key
Beautiful Beach Cottage 2 Bed/2 Bath 10 Minutes To Siesta Key Beach and Downtown
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House Siesta Key
Stunning Siesta Key,, ., Walk to Shell Beach, HEATED POOL 10
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Condo Siesta Key
Condo with heated pool, patio & barbeque
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House Siesta Key
Beach Access, Pools, Tennis and Pickleball - 1225 Gulf & Bayside
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House Siesta Key
Doveplum 112- 3 Story, 4 Bedroom Condo with Private Beach with lounge chairs & umbrella provided,...
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Condo Siesta Key
Condo with heated pool & barbeque
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House Siesta Key
SIESTA KEY 1 BEACH: 4 COTTAGES: RENT 1,2,3 OR ALL 4! PRICE HERE IS FOR 1 COTTAGE
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House Siesta Key
Child-friendly ample house with terrace, private pool & barbeque | Perfect for remote work | Dogs allowed
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House Siesta Key
Waterfront ranch home near Siesta Key with pool overlooking canal and kayaks.
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House Siesta Key
Vacation home with hot tub, private pool & grill
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Cabin Siesta Key
5 Min walk to Beach & Village, Private Pool, On the Canal
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Condo Siesta Key
Anchorage Resort 7th Floor 2-Bedroom Condo w Private Balcony Beach Access
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House Siesta Key
Beach front paradise located in a Condo Building Beach front Penthouse!
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House Siesta Key
Luxury Sarasota Waterfront Home - Pool, Boat Dock & Near Siesta Key Beach
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House Siesta Key
Nothing Comparable on Siesta Key to 4BR Beachfront - Right on 1 Rated Beach
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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 8,022 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Villa Siesta Key
Villa ∙ 10 guests ∙ 4 bedrooms

Nice villa with pool, patio & grill | Next to the beach

Siesta Key, Sarasota County, Florida, United States
This spacious villa in Siesta Key accommodates 10 guests and features a modern kitchen ideal for family gatherings.
from $650
per night
(17)
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House Siesta Key
House ∙ 8 guests ∙ 3 bedrooms

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

Siesta Key, Sarasota County, Florida, United States
This house rental in Siesta Key accommodates 8 guests and features a heated pool for a relaxing getaway.
from $256
per night
(2)
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House Siesta Key
House ∙ 6 guests ∙ 3 bedrooms

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

Siesta Key, Sarasota County, Florida, United States
This house rental in Sarasota accommodates 6 guests and features a private pool for a relaxing getaway.
from $307
per night
(53)
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House Siesta Key
House ∙ 8 guests ∙ 3 bedrooms

House with pool

Siesta Key, Sarasota County, Florida, United States
This spacious condo in Siesta Key accommodates 8 guests and features a lovely balcony for enjoying the scenic views.
from $604
per night
(2)
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House Siesta Key
House ∙ 16 guests ∙ 5 bedrooms

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

Siesta Key, Sarasota County, Florida, United States
This spacious house rental in Siesta Key accommodates 16 guests and features a private pool for a relaxing getaway.
from $296
per night
(2)
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House Siesta Key
House ∙ 7 guests ∙ 4 bedrooms

Vacation home with patio, hot tub & private pool

Siesta Key, Sarasota County, Florida, United States
This house rental in Sarasota accommodates 7 guests and features a private pool for a relaxing getaway.
from $259
per night
(44)
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Condo Siesta Key
Condo ∙ 3 guests ∙ 1 bedroom

Condo with patio | City view

Siesta Key, Sarasota County, Florida, United States
This condo in Lido Key accommodates 3 guests and features a fully equipped kitchen for convenient meal preparation.
from $178
per night
(234)
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House Siesta Key
House ∙ 10 guests ∙ 4 bedrooms

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

Siesta Key, Sarasota County, Florida, United States
This house rental in Sarasota accommodates 10 guests and features a private pool for a relaxing stay.
from $265
per night
(51)
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Condo Siesta Key
Condo ∙ 8 guests ∙ 3 bedrooms

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

Siesta Key, Sarasota County, Florida, United States
This spacious 8-person condo in Siesta Key features a heated pool for relaxation and enjoyment.
from $179
per night
(42)
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