House holiday rentals in Siesta Key
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Top-rated house rentals in Siesta Key
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Siesta Key house rentals
House rentals with a pool
Home in Siesta Key
4.87 out of 5 average rating, 119 reviews"Safe & Clean" Palm Oasis - Relax in comfort!
9–16 Dec
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
19–26 Aug
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
25 Aug – 1 Sep
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
22–29 Nov
Home in Sarasota
4.94 out of 5 average rating, 296 reviews☀Coastal Gem☀Heated pool & amazing location!☀
2–9 Aug
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
19–26 Sep
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
7–14 Nov
Home in Siesta Key
4.89 out of 5 average rating, 139 reviewsSiesta Beach House
4–11 Sep
Weekly house rentals
Home in Sarasota
4.85 out of 5 average rating, 162 reviewsAuthentic Florida Bungalow near Downtown and Beach
26 Jun – 3 Jul
Home in Sarasota
5.0 out of 5 average rating, 29 reviewsSiesta Key Fully-Renovated Unit 5 min to the beach
26 Sep – 3 Oct
Home in Sarasota
5.0 out of 5 average rating, 20 reviewsThe Mango House Beach Cottage
15–22 Aug
Home in Sarasota
4.98 out of 5 average rating, 47 reviews2 bedroom 1 bath 7 mins to the beach
9–16 May
Home in Siesta Key
5.0 out of 5 average rating, 7 reviewsVintage Coastal
13–20 Sep
Home in Siesta Key
5.0 out of 5 average rating, 22 reviewsBeachfront 180-Degree View, Walk to Village!
21–28 Sep
Home in Sarasota
4.89 out of 5 average rating, 47 reviewsCentrally Located Cozy Home
17–24 Sep
Home in Sarasota
5.0 out of 5 average rating, 5 reviewsCute 2 bedroom home close to it all.
31 Aug – 7 Sep
Private house rentals
Home in Sarasota
4.96 out of 5 average rating, 24 reviewsBeach house #2
14–21 Jan
Home in Siesta Key
4.95 out of 5 average rating, 88 reviewsBeachfront home with private access, walk to town!
24 Nov – 1 Dec
Home in Siesta Key
5.0 out of 5 average rating, 25 reviewsLuxe Siesta Key Home| Pool + Hot Tub| Near Beach
10–17 Dec
Home in Sarasota
5.0 out of 5 average rating, 5 reviewsCozy Heaven Studio III
10–17 Nov
Home in Siesta Key
5.0 out of 5 average rating, 20 reviewsIn Village, Steps to Beach, Pool, Ocean-view!
10–17 Dec
Home in Sarasota
5.0 out of 5 average rating, 10 reviewsFruit /Botanical Garden Estate 2 miles to downtown
14–21 Aug
Home in Sarasota
5.0 out of 5 average rating, 26 reviewsFamily friendly with large pool
29 Aug – 5 Sep
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsBrand New Luxury Home w/ Pool & Putting Green
10–17 Sep
Quick stats about house rentals in Siesta Key
Total rentals
410 properties
Rentals with dedicated workspaces
270 properties have a dedicated workspace
Rentals with a pool
290 properties have a pool
Pet-friendly rentals
190 properties allow pets
Family-friendly rentals
370 properties are a good fit for families
Total number of reviews
6.1K reviews
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